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2141 Harbourside Drive Unit 1203, Longboat Key

Welcome to an exceptional turnkey, furnished, and newly renovated villa in Harbour Oaks, ideally located within Bay Isles in the heart of Longboat Key. This end-unit residence offers the right blend of natural warmth, contemporary finishes, and curated style. With high ceilings, abundant natural light, and a spacious floor plan, the home feels remarkably open and inviting. Warm hickory wood floors extend throughout the living areas, adding richness and character to the home's fresh, contemporary design. The impressive kitchen features an oversized island with a dramatic waterfall-edge quartz countertop in a concrete-inspired finish that is both beautiful and requires no maintenance. Stainless steel GE Café appliances complement the kitchen, while a custom coffee bar with floating shelves and a stunning backsplash adds another layer of style and functionality. For evening entertaining, the custom built-in bar is a standout feature, topped with a beautiful live-edge Saman wood countertop. It is the perfect place to pour a cocktail and enjoy the relaxed Longboat Key lifestyle. The spacious dining area is adjacent to a beautiful atrium that fills the home with magnificent natural light. Newly tiled with stone. It is screened overhead, allowing the sliders to be opened, creating a wonderful connection to the outdoors and inviting fresh air into the dining and living space. The oversized screened lanai is another exceptional feature, with brand-new stone pavers and a new panoramic screen enclosure. Lush new greenery surrounds the lanai, creating a private tropical setting that feels like your own outdoor retreat. The primary suite is a luxurious sanctuary with three closets, including a walk-in, all outfitted with customized shelving for exceptional organization. The beautifully renovated primary bath features Carrera marble countertops, dual sinks, warm gold fixtures, and a separate water closet. The spacious second bedroom offers a private ensuite bath with a marble-floored shower, Carrera marble vanity top, and a separate water closet. The generous third bedroom is currently used as a fitness room but offers ample space for a comfortable bedroom, along with a generous closet. Storage is abundant throughout the home. A beautifully appointed powder room serves guests. As an end unit, this villa enjoys a large manicured grass side yard and an enviable location just steps from the community pool. This home has an attached 2-car garage with a new epoxy-coated floor and an additional fridge. An especially wonderful benefit of living in Bay Isles is automatic membership in the Bay Isles Beach Club, just minutes away on Longboat Key's beautiful sandy beaches. Enjoy five acres of beachfront, gated parking, beach chair storage, newly renovated restrooms, grills and picnic tables—a wonderful setting for family and friends to gather, sunset strolls, and memories to last a lifetime. Close proximity to the Longboat Key Club with 45 holes of golf, 5 private restaurants, and a world-class tennis and pickleball facility. This residence is more than a renovation; it is a completely reimagined home where thoughtful design, beautiful materials, and the ease of living the good life on Longboat Key come together beautifully.

3 Beds ⋅ 3 Baths ⋅ Harbour Oaks SubDv. ⋅ 34228 Zip Code

Welcome to an exceptional turnkey, furnished, and newly renovated villa in Harbour Oaks, ideally located within Bay Isles in the heart of Longboat Key. This end-unit residence offers the right blend of natural warmth, contemporary finishes, and curated style. With high ceilings, abundant natural light, and a spacious floor plan, the home feels remarkably open and inviting. Warm hickory wood floors extend throughout the living areas, adding richness and character to the home's fresh, contemporary design. The impressive kitchen features an oversized island with a dramatic waterfall-edge quartz countertop in a concrete-inspired finish that is both beautiful and requires no maintenance. Stainless steel GE Café appliances complement the kitchen, while a custom coffee bar with floating shelves and a stunning backsplash adds another layer of style and functionality. For evening entertaining, the custom built-in bar is a standout feature, topped with a beautiful live-edge Saman wood countertop. It is the perfect place to pour a cocktail and enjoy the relaxed Longboat Key lifestyle. The spacious dining area is adjacent to a beautiful atrium that fills the home with magnificent natural light. Newly tiled with stone. It is screened overhead, allowing the sliders to be opened, creating a wonderful connection to the outdoors and inviting fresh air into the dining and living space. The oversized screened lanai is another exceptional feature, with brand-new stone pavers and a new panoramic screen enclosure. Lush new greenery surrounds the lanai, creating a private tropical setting that feels like your own outdoor retreat. The primary suite is a luxurious sanctuary with three closets, including a walk-in, all outfitted with customized shelving for exceptional organization. The beautifully renovated primary bath features Carrera marble countertops, dual sinks, warm gold fixtures, and a separate water closet. The spacious second bedroom offers a private ensuite bath with a marble-floored shower, Carrera marble vanity top, and a separate water closet. The generous third bedroom is currently used as a fitness room but offers ample space for a comfortable bedroom, along with a generous closet. Storage is abundant throughout the home. A beautifully appointed powder room serves guests. As an end unit, this villa enjoys a large manicured grass side yard and an enviable location just steps from the community pool. This home has an attached 2-car garage with a new epoxy-coated floor and an additional fridge. An especially wonderful benefit of living in Bay Isles is automatic membership in the Bay Isles Beach Club, just minutes away on Longboat Key's beautiful sandy beaches. Enjoy five acres of beachfront, gated parking, beach chair storage, newly renovated restrooms, grills and picnic tables—a wonderful setting for family and friends to gather, sunset strolls, and memories to last a lifetime. Close proximity to the Longboat Key Club with 45 holes of golf, 5 private restaurants, and a world-class tennis and pickleball facility. This residence is more than a renovation; it is a completely reimagined home where thoughtful design, beautiful materials, and the ease of living the good life on Longboat Key come together beautifully.

2141 Harbourside Drive Unit 1203, Longboat Key

845 Spanish Drive N Unit 845, Longboat Key

$450,000

Positioned directly across from the marina and boat slips, this updated villa in Spanish Main Yacht Club enjoys beautiful marina views and puts boating and waterfront access just steps from your front door, while offering the relaxed island lifestyle and everyday convenience of a 55+ waterfront community on Longboat Key. The villa features 2 bedrooms, 2 bathrooms, and a flexible third room that could potentially be converted into a third bedroom, giving you added space for guests, a home office, workout area, or den. Tile flooring runs throughout, while the renovated kitchen features quartz countertops, stainless steel appliances, new cabinetry, and dovetail soft-close drawers. The primary suite offers its own private bath and walk-in closet, while the guest bedroom and second bath are positioned separately for added privacy. The home also features an interior washer and dryer combo, offering added everyday convenience compared with the exterior laundry setups found in many neighboring units. Spanish Main Yacht Club offers a community pool, clubhouse, marina, water access, and deeded beach access just across Gulf of Mexico Drive. Additional parking across the street provides extra convenience for guests and visitors. Here, days can be spent enjoying the marina views, relaxing at the private beach, lounging by the pool, or heading out on the water, with local dining, parks, and island conveniences nearby. Boat slips are available separately through the association as availability allows. Whether you’re looking for a full-time residence or seasonal retreat, this villa offers the updates, setting, and waterfront lifestyle that make Spanish Main Yacht Club such a special place to enjoy Longboat Key.

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

Positioned directly across from the marina and boat slips, this updated villa in Spanish Main Yacht Club enjoys beautiful marina views and puts boating and waterfront access just steps from your front door, while offering the relaxed island lifestyle and everyday convenience of a 55+ waterfront community on Longboat Key. The villa features 2 bedrooms, 2 bathrooms, and a flexible third room that could potentially be converted into a third bedroom, giving you added space for guests, a home office, workout area, or den. Tile flooring runs throughout, while the renovated kitchen features quartz countertops, stainless steel appliances, new cabinetry, and dovetail soft-close drawers. The primary suite offers its own private bath and walk-in closet, while the guest bedroom and second bath are positioned separately for added privacy. The home also features an interior washer and dryer combo, offering added everyday convenience compared with the exterior laundry setups found in many neighboring units. Spanish Main Yacht Club offers a community pool, clubhouse, marina, water access, and deeded beach access just across Gulf of Mexico Drive. Additional parking across the street provides extra convenience for guests and visitors. Here, days can be spent enjoying the marina views, relaxing at the private beach, lounging by the pool, or heading out on the water, with local dining, parks, and island conveniences nearby. Boat slips are available separately through the association as availability allows. Whether you’re looking for a full-time residence or seasonal retreat, this villa offers the updates, setting, and waterfront lifestyle that make Spanish Main Yacht Club such a special place to enjoy Longboat Key.

845 Spanish Drive N Unit 845, Longboat Key

2550 Harbourside Drive Unit 334, Longboat Key

$1,400,000

Waterfront. Exquisite Bay Views. Deeded beach access. Bring your contractor and your imagination. This 3 Bedroom, 3 Bathroom, sun-filled unit lives large with over 3000 sqft of living space and wraparound balconies to capture all the magnificent views. Freshly painted and sparkling clean. Updates include a new roof 2025, 2 water heaters (2022), 2 A/C units (2022). Priced below appraised value. Marina Bay is pet-friendly, allowing one pet up to 25 lbs. Boat slips are available for purchase or lease, subject to availability. The Bay Isles Beach Club adds another dimension to island life. This private Gulf-front retreat offers gated entry, parking, restrooms, showers, and shaded seating along a beautiful stretch of sandy beach.Enjoy nearby shopping and exceptional dining. For those seeking additional recreation and social opportunities, optional membership at the Longboat Key Club offers golf, tennis, pickleball, beach club access, marina facilities, spa and wellness amenities, several dining venues, and an active social calendar. Expansive bay views, room to spread out, and access to both boating and the beach create a wonderful opportunity to shape your own Longboat Key lifestyle. Make an appointment today!

3 Beds ⋅ 3 Baths ⋅ Longboat Key Club SubDv. ⋅ 34228 Zip Code

Waterfront. Exquisite Bay Views. Deeded beach access. Bring your contractor and your imagination. This 3 Bedroom, 3 Bathroom, sun-filled unit lives large with over 3000 sqft of living space and wraparound balconies to capture all the magnificent views. Freshly painted and sparkling clean. Updates include a new roof 2025, 2 water heaters (2022), 2 A/C units (2022). Priced below appraised value. Marina Bay is pet-friendly, allowing one pet up to 25 lbs. Boat slips are available for purchase or lease, subject to availability. The Bay Isles Beach Club adds another dimension to island life. This private Gulf-front retreat offers gated entry, parking, restrooms, showers, and shaded seating along a beautiful stretch of sandy beach.Enjoy nearby shopping and exceptional dining. For those seeking additional recreation and social opportunities, optional membership at the Longboat Key Club offers golf, tennis, pickleball, beach club access, marina facilities, spa and wellness amenities, several dining venues, and an active social calendar. Expansive bay views, room to spread out, and access to both boating and the beach create a wonderful opportunity to shape your own Longboat Key lifestyle. Make an appointment today!

2550 Harbourside Drive Unit 334, Longboat Key

$425,000

Virtually Staged. Welcome to Spanish Main Yacht Club waterfront community and your new home! Light and bright, this stand-alone villa is all new and beautifully updated in 2026. White marble-like large porcelain tile floors that span the entire living area, providing a continuous flow throughout the villa. The new kitchen boasts stainless steel appliances, white quartz countertops, new cabinetry, lighting and more. Attractive updates in the primary en suite bedroom and guest bath as well. A nice added feature is the spacious interior laundry room. Beautiful, lush backyard view with privacy and an extra brick paver side yard and outdoor space. A short stroll to the privately deeded beach entrance to gorgeous Gulf beaches. Two minutes to have your toes in the soft, pearly sand. This is a boater’s paradise with slips available for an extremely inexpensive lease and direct access to Sarasota Bay, the Intracoastal waterway and azure waters of the Gulf. Only a short drive to the fantastic shops, restaurants and cultural events Sarasota and St. Armands Circle have to offer. This is a great investment opportunity and chance to enjoy Longboat Key living. The community is in the build-back stage due to damage from hurricanes in 2024 and is almost complete. All 212 units in Spanish Main are under FEMA requirements, guidelines, and stringent adherence to rebuild specifications and inspections from Town of Longboat Key. This is an opportunity to continue to make this villa your custom home.

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

Virtually Staged. Welcome to Spanish Main Yacht Club waterfront community and your new home! Light and bright, this stand-alone villa is all new and beautifully updated in 2026. White marble-like large porcelain tile floors that span the entire living area, providing a continuous flow throughout the villa. The new kitchen boasts stainless steel appliances, white quartz countertops, new cabinetry, lighting and more. Attractive updates in the primary en suite bedroom and guest bath as well. A nice added feature is the spacious interior laundry room. Beautiful, lush backyard view with privacy and an extra brick paver side yard and outdoor space. A short stroll to the privately deeded beach entrance to gorgeous Gulf beaches. Two minutes to have your toes in the soft, pearly sand. This is a boater’s paradise with slips available for an extremely inexpensive lease and direct access to Sarasota Bay, the Intracoastal waterway and azure waters of the Gulf. Only a short drive to the fantastic shops, restaurants and cultural events Sarasota and St. Armands Circle have to offer. This is a great investment opportunity and chance to enjoy Longboat Key living. The community is in the build-back stage due to damage from hurricanes in 2024 and is almost complete. All 212 units in Spanish Main are under FEMA requirements, guidelines, and stringent adherence to rebuild specifications and inspections from Town of Longboat Key. This is an opportunity to continue to make this villa your custom home.

554 Spanish Drive S, Longboat Key

$15,000,000

Be renewed and inspired by this striking Gulf-front residence in an exclusive island community, featuring an impressive 100 feet of direct beachfront. Renovated and redesigned in 2025 to offer seamless indoor-outdoor integration and wide, unobstructed Gulf views, the setting is simply spectacular. This sophisticated contemporary masterpiece captures the relaxed spirit of beachfront living through clean lines, organic textures, and a crisp, minimalist aesthetic, creating a space that feels airy, bright, and deeply connected to nature. Interior layouts embrace high ceilings and expansive open-plan living zones that share light across the entire footprint through vast expanses of glass. The distinctive 6,660-square-foot beach house blends rigorous structural engineering with minimalist design to celebrate the coastal environment. Luxury finishes and fixtures include Louis XIV champagne White Oak floors, Dennis & Leen custom chandeliers and sconces, and a custom Murano glass chandelier. The living room, dining room, and kitchen span nearly 1,200 square feet of open living, enhanced by a dramatic two-story ceiling and seamless access to the oversized lanai. Multiple sets of triple-glazed sliders open wide, dissolving the boundaries between indoors and out and creating a dramatic setting for effortless entertaining, relaxed gatherings, and unforgettable open-air living. In addition to mesmerizing tropical views and a light-drenched workspace, the extraordinary kitchen and butler’s pantry feature marble counters and high-end appliances, including a Wolf double-range oven, a Wolf steam oven, an integrated Sub-Zero refrigerator and freezer, and two Sub-Zero beverage refrigerators. Elevated to showcase the 180-degree unobstructed horizon views, a glamorous primary suite offers an exquisite bath surrounded by plush comfort amenities, with gorgeous vistas dominating the space. Two additional en-suite bedrooms, a third bedroom currently used as an office with a bath, and a loft library with a long wall of built-in bookcases offer plenty of room for everyone to unwind and rejuvenate at day’s end. The ground-floor space has 2 garage doors for vehicle and water-toy access, an elevator to the second and third levels, a huge lounge with abundant seating, a large-screen TV, an adjoining exercise room, and 2 mini-split air conditioners dedicated to this enormous ground-level space. Notable features throughout the house include 5 full bathrooms, a laundry room with marble counters and flooring, a water filtration system and softener, a Generac generator, a security system with ten cameras, and a Sonos audio system. Outdoor living is integral to this exceptional beachside residence, with multiple levels designed to capture breathtaking water panoramas and embrace the surrounding beauty. Spanning the entire Gulf-facing façade, a covered ground-level patio, a second-level lanai, and a third-level balcony create an effortless progression of spaces for relaxing, entertaining, and enjoying spectacular sunsets. A truly exceptional beachside retreat, 6529 Gulfside Road delivers a refined coastal experience that embraces everything that makes Florida living so extraordinary. From its spectacular setting to its thoughtfully designed spaces, every element celebrates the beauty, ease, and allure of Gulfside living. *Variance in place and plans drawn for 1,000 sq. ft. guest house and pool, making the square footage over 7,500 under air.

5 Beds ⋅ 5 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code

Be renewed and inspired by this striking Gulf-front residence in an exclusive island community, featuring an impressive 100 feet of direct beachfront. Renovated and redesigned in 2025 to offer seamless indoor-outdoor integration and wide, unobstructed Gulf views, the setting is simply spectacular. This sophisticated contemporary masterpiece captures the relaxed spirit of beachfront living through clean lines, organic textures, and a crisp, minimalist aesthetic, creating a space that feels airy, bright, and deeply connected to nature. Interior layouts embrace high ceilings and expansive open-plan living zones that share light across the entire footprint through vast expanses of glass. The distinctive 6,660-square-foot beach house blends rigorous structural engineering with minimalist design to celebrate the coastal environment. Luxury finishes and fixtures include Louis XIV champagne White Oak floors, Dennis & Leen custom chandeliers and sconces, and a custom Murano glass chandelier. The living room, dining room, and kitchen span nearly 1,200 square feet of open living, enhanced by a dramatic two-story ceiling and seamless access to the oversized lanai. Multiple sets of triple-glazed sliders open wide, dissolving the boundaries between indoors and out and creating a dramatic setting for effortless entertaining, relaxed gatherings, and unforgettable open-air living. In addition to mesmerizing tropical views and a light-drenched workspace, the extraordinary kitchen and butler’s pantry feature marble counters and high-end appliances, including a Wolf double-range oven, a Wolf steam oven, an integrated Sub-Zero refrigerator and freezer, and two Sub-Zero beverage refrigerators. Elevated to showcase the 180-degree unobstructed horizon views, a glamorous primary suite offers an exquisite bath surrounded by plush comfort amenities, with gorgeous vistas dominating the space. Two additional en-suite bedrooms, a third bedroom currently used as an office with a bath, and a loft library with a long wall of built-in bookcases offer plenty of room for everyone to unwind and rejuvenate at day’s end. The ground-floor space has 2 garage doors for vehicle and water-toy access, an elevator to the second and third levels, a huge lounge with abundant seating, a large-screen TV, an adjoining exercise room, and 2 mini-split air conditioners dedicated to this enormous ground-level space. Notable features throughout the house include 5 full bathrooms, a laundry room with marble counters and flooring, a water filtration system and softener, a Generac generator, a security system with ten cameras, and a Sonos audio system. Outdoor living is integral to this exceptional beachside residence, with multiple levels designed to capture breathtaking water panoramas and embrace the surrounding beauty. Spanning the entire Gulf-facing façade, a covered ground-level patio, a second-level lanai, and a third-level balcony create an effortless progression of spaces for relaxing, entertaining, and enjoying spectacular sunsets. A truly exceptional beachside retreat, 6529 Gulfside Road delivers a refined coastal experience that embraces everything that makes Florida living so extraordinary. From its spectacular setting to its thoughtfully designed spaces, every element celebrates the beauty, ease, and allure of Gulfside living. *Variance in place and plans drawn for 1,000 sq. ft. guest house and pool, making the square footage over 7,500 under air.

6529 Gulfside Road, Longboat Key

600 Sutton Place Unit 101B, Longboat Key

$319,000

Waterfront condo with Sarasota Bay views! Perfectly positioned along Sarasota Bay on **Longboat Key** and just steps from the turquoise waters of the **Gulf of Mexico**, this exceptional community offers the ultimate coastal lifestyle in an unbeatable location. Current owners have never had water intrusion from any hurricanes. This spacious ground-floor corner residence features an expansive open-concept layout designed to comfortably accommodate up to six guests. The beautifully remodeled kitchen showcases stainless steel appliances, a brand-new range, granite countertops, stone backsplash, recessed lighting, and solid wood cabinetry — blending modern style with everyday functionality. A charming nook provides the perfect space for additional sleeping accommodations or a cozy retreat to enjoy serene bay views. Impact-rated sliding glass doors open seamlessly to the outdoors and are complemented by brand-new Shade Store cellular window treatments. Relax while taking in peaceful water and pool views from the comfort of your living space. The spacious primary bedroom features custom cellular shades with top and bottom openings to maximize natural light and views, along with a walk-in closet complete with built-ins. The ensuite bath has been thoughtfully updated with a newer vanity and a brand-new shower remodel (2025), offering a fresh, modern feel. Furnishings are optional and tastefully curated with designer touches, making this property move-in or rental ready. Exceptional Community Amenities - Residents enjoy a truly unique waterfront lifestyle: Two heated pools, Marina and clubhouse, Available boat slips for rent, fish-cleaning station, Kayak storage with electric launch, BBQ grilling areas, Car wash station, Lighted assigned carport parking, Elevator access, Private storage unit (3rd floor), Laundry facility (2nd floor), exclusive deeded beach access on Longboat Key, featuring a pavilion, storage lockers, indoor showers, and restrooms. Enjoy watching dolphins and manatees from the bayfront grounds, spend your days fishing or kayaking, or relax on the sugar-sand beaches just across the street. The community is also in the planning stages of adding a brand-new state-of-the-art fitness center. Shopping and dining are just minutes away at the renowned **St. Armands Circle**. Experience the best of both worlds — Gulf-front beach days and tranquil bayfront evenings. This is coastal living at its finest.

1 Beds ⋅ 1 Baths ⋅ Sutton Place Condo SubDv. ⋅ 34228 Zip Code

Waterfront condo with Sarasota Bay views! Perfectly positioned along Sarasota Bay on **Longboat Key** and just steps from the turquoise waters of the **Gulf of Mexico**, this exceptional community offers the ultimate coastal lifestyle in an unbeatable location. Current owners have never had water intrusion from any hurricanes. This spacious ground-floor corner residence features an expansive open-concept layout designed to comfortably accommodate up to six guests. The beautifully remodeled kitchen showcases stainless steel appliances, a brand-new range, granite countertops, stone backsplash, recessed lighting, and solid wood cabinetry — blending modern style with everyday functionality. A charming nook provides the perfect space for additional sleeping accommodations or a cozy retreat to enjoy serene bay views. Impact-rated sliding glass doors open seamlessly to the outdoors and are complemented by brand-new Shade Store cellular window treatments. Relax while taking in peaceful water and pool views from the comfort of your living space. The spacious primary bedroom features custom cellular shades with top and bottom openings to maximize natural light and views, along with a walk-in closet complete with built-ins. The ensuite bath has been thoughtfully updated with a newer vanity and a brand-new shower remodel (2025), offering a fresh, modern feel. Furnishings are optional and tastefully curated with designer touches, making this property move-in or rental ready. Exceptional Community Amenities - Residents enjoy a truly unique waterfront lifestyle: Two heated pools, Marina and clubhouse, Available boat slips for rent, fish-cleaning station, Kayak storage with electric launch, BBQ grilling areas, Car wash station, Lighted assigned carport parking, Elevator access, Private storage unit (3rd floor), Laundry facility (2nd floor), exclusive deeded beach access on Longboat Key, featuring a pavilion, storage lockers, indoor showers, and restrooms. Enjoy watching dolphins and manatees from the bayfront grounds, spend your days fishing or kayaking, or relax on the sugar-sand beaches just across the street. The community is also in the planning stages of adding a brand-new state-of-the-art fitness center. Shopping and dining are just minutes away at the renowned **St. Armands Circle**. Experience the best of both worlds — Gulf-front beach days and tranquil bayfront evenings. This is coastal living at its finest.

600 Sutton Place Unit 101B, Longboat Key

4380 Exeter Drive Unit 101, Longboat Key

$389,500

Virtually Staged. Investor alert. Great investment opportunity! Condominium is in great condition. Best price for two-bedroom, two-bath condominium in sought after community of Longboat Harbour. Motivated sellers, ready to have a new buyer enjoy this lovely waterfront first-floor end-unit condominium. New roof, all assessments paid, granite countertops, kitchen open to living area. All glass lanai, tile throughout main living, carpet in bedrooms were in the bedrooms but carpet removed for new flooring to be installed. A huge plus: end unit, close to the beach, washer and dryer are in the unit. Hurricane shutters on rear of unit. Additionally, the beautifully renovated recreation room overlooking the bay serves as heart of social gatherings in Longboat Harbour, hosting a variety of clubs and activities complemented by a kitchen and dance floor. The four heated swimming pools provide relaxation and enjoyment year-round. For beach lovers, a community beach pavilion across Gulf of Mexico Drive offers residents private, private deeded beach access with a cabana, parking, restrooms and dressing areas. Witness breathtaking sunrises, spot manatees and savor stunning sunsets along the Gulf beach. This exceptional opportunity offers an unparalleled lifestyle in one of Longboat Key's active, social and vibrant communities! Seize the opportunity to experience waterfront living at its finest. This condominium community was not impacted by hurricane flood waters, according to the owner. Make this beautiful community your next home!

2 Beds ⋅ 2 Baths ⋅ Longboat Harbour Towers SubDv. ⋅ 34228 Zip Code

Virtually Staged. Investor alert. Great investment opportunity! Condominium is in great condition. Best price for two-bedroom, two-bath condominium in sought after community of Longboat Harbour. Motivated sellers, ready to have a new buyer enjoy this lovely waterfront first-floor end-unit condominium. New roof, all assessments paid, granite countertops, kitchen open to living area. All glass lanai, tile throughout main living, carpet in bedrooms were in the bedrooms but carpet removed for new flooring to be installed. A huge plus: end unit, close to the beach, washer and dryer are in the unit. Hurricane shutters on rear of unit. Additionally, the beautifully renovated recreation room overlooking the bay serves as heart of social gatherings in Longboat Harbour, hosting a variety of clubs and activities complemented by a kitchen and dance floor. The four heated swimming pools provide relaxation and enjoyment year-round. For beach lovers, a community beach pavilion across Gulf of Mexico Drive offers residents private, private deeded beach access with a cabana, parking, restrooms and dressing areas. Witness breathtaking sunrises, spot manatees and savor stunning sunsets along the Gulf beach. This exceptional opportunity offers an unparalleled lifestyle in one of Longboat Key's active, social and vibrant communities! Seize the opportunity to experience waterfront living at its finest. This condominium community was not impacted by hurricane flood waters, according to the owner. Make this beautiful community your next home!

4380 Exeter Drive Unit 101, Longboat Key

340 Gulf Of Mexico Drive Unit 136, Longboat Key

$2,995,000

Rarely available and distinctly different from traditional condominium living, this two-level penthouse at Tangerine Bay Club pairs nearly 3,000 square feet of beautifully reimagined interiors with sweeping bay views and the privacy of a single-family home. Positioned on a coveted south-facing corner, Residence #136 captures an extraordinary panorama encompassing the bay, downtown Sarasota skyline and protected mangrove preserves. Two generous terraces, a private courtyard entry and a private two-car garage further distinguish this exceptional residence. Inside, the renovation strikes a sophisticated balance between coastal ease and thoughtful design. Soaring vaulted ceilings amplify the natural light, while expansive walls of glass keep bay vistas at the forefront of the main living spaces. A gas fireplace and custom entertainment wall create a dramatic focal point, and direct access to the terraces extends everyday living and entertaining outdoors. Impact-rated Andersen windows, motorized storm shutters, custom LED lighting and California Closets add another layer of comfort and functionality. At the heart of the main level, the gourmet kitchen was designed as much for entertaining as for the serious home chef. Honed marble countertops complement a substantial leathered-stone island and custom cabinetry. A remarkable collection of appliances and culinary features includes a La Cornue dual-fuel range with French plate, Flamberge rotisserie oven, galley sink, wine cooler and Sub-Zero beverage drawers. An adjoining breakfast area provides a relaxed place to begin the day, while the formal dining area accommodates larger gatherings against the backdrop of the residence’s open living spaces. Privately positioned, the primary suite is a serene retreat with direct terrace access, custom closets and a beautifully appointed spa-inspired bath. Quartz surfaces, dual vanities, a freestanding soaking tub and expansive walk-in steam shower create a luxurious setting. Also on the main level, the second bedroom is currently arranged as a den with a nearby full bath, providing flexibility for guests, an office or additional living space. Upstairs, the home reveals another dimension: a lofted lounge with custom built-ins overlooks the living areas below, while a private third en-suite bedroom creates an ideal retreat for visiting family and friends. The separation between levels allows the residence to live comfortably whether hosting a full house or enjoying it as a private island escape. Outdoor living is equally compelling. Two terraces capitalize on the penthouse’s south-facing orientation and elevated perspective. Combined with the private courtyard entrance and two-car garage, these spaces reinforce the feeling of a home. Tangerine Bay Club is one of Longboat Key’s distinctive resort-style communities, recognized for its lush mature landscaping and exceptional location at the southern end of the island. Residents enjoy a 25-meter heated pool and spa set on a private island, tennis and pickleball, fitness, kayak launch, walking paths and a day dock available on a first-come basis. Adding to the community’s appeal, Tangerine Bay Club successfully completed its milestone inspection without requiring repairs, maintains healthy reserves and, at this time, has no special assessments anticipated. Optional membership to the Bay Isles Beach Club provides access to a private beach, adding another dimension to the Longboat Key lifestyle.

3 Beds ⋅ 4 Baths ⋅ Tangerine Bay Club SubDv. ⋅ 34228 Zip Code

Rarely available and distinctly different from traditional condominium living, this two-level penthouse at Tangerine Bay Club pairs nearly 3,000 square feet of beautifully reimagined interiors with sweeping bay views and the privacy of a single-family home. Positioned on a coveted south-facing corner, Residence #136 captures an extraordinary panorama encompassing the bay, downtown Sarasota skyline and protected mangrove preserves. Two generous terraces, a private courtyard entry and a private two-car garage further distinguish this exceptional residence. Inside, the renovation strikes a sophisticated balance between coastal ease and thoughtful design. Soaring vaulted ceilings amplify the natural light, while expansive walls of glass keep bay vistas at the forefront of the main living spaces. A gas fireplace and custom entertainment wall create a dramatic focal point, and direct access to the terraces extends everyday living and entertaining outdoors. Impact-rated Andersen windows, motorized storm shutters, custom LED lighting and California Closets add another layer of comfort and functionality. At the heart of the main level, the gourmet kitchen was designed as much for entertaining as for the serious home chef. Honed marble countertops complement a substantial leathered-stone island and custom cabinetry. A remarkable collection of appliances and culinary features includes a La Cornue dual-fuel range with French plate, Flamberge rotisserie oven, galley sink, wine cooler and Sub-Zero beverage drawers. An adjoining breakfast area provides a relaxed place to begin the day, while the formal dining area accommodates larger gatherings against the backdrop of the residence’s open living spaces. Privately positioned, the primary suite is a serene retreat with direct terrace access, custom closets and a beautifully appointed spa-inspired bath. Quartz surfaces, dual vanities, a freestanding soaking tub and expansive walk-in steam shower create a luxurious setting. Also on the main level, the second bedroom is currently arranged as a den with a nearby full bath, providing flexibility for guests, an office or additional living space. Upstairs, the home reveals another dimension: a lofted lounge with custom built-ins overlooks the living areas below, while a private third en-suite bedroom creates an ideal retreat for visiting family and friends. The separation between levels allows the residence to live comfortably whether hosting a full house or enjoying it as a private island escape. Outdoor living is equally compelling. Two terraces capitalize on the penthouse’s south-facing orientation and elevated perspective. Combined with the private courtyard entrance and two-car garage, these spaces reinforce the feeling of a home. Tangerine Bay Club is one of Longboat Key’s distinctive resort-style communities, recognized for its lush mature landscaping and exceptional location at the southern end of the island. Residents enjoy a 25-meter heated pool and spa set on a private island, tennis and pickleball, fitness, kayak launch, walking paths and a day dock available on a first-come basis. Adding to the community’s appeal, Tangerine Bay Club successfully completed its milestone inspection without requiring repairs, maintains healthy reserves and, at this time, has no special assessments anticipated. Optional membership to the Bay Isles Beach Club provides access to a private beach, adding another dimension to the Longboat Key lifestyle.

340 Gulf Of Mexico Drive Unit 136, Longboat Key

$529,990

BACK AND BETTER THAN EVER! This completely renovated, turnkey furnished 2BR/2BA villa in the coveted 55+ Spanish Main Yacht Club returns to market with a NEW ROOF and NEW HVAC, both with transferable warranties. A prior appraisal documents 1,393 SF of above grade living space, offering more room than previously reflected in the MLS. The home also features impact windows and doors, adding peace of mind and year round durability as well as a full house water filtration system. Step outside to your spacious private patio—perfect for grilling, relaxing, and enjoying the coastal breeze. From there, take a short stroll across the road to your deeded Gulf beach access, or walk just a few steps to the deep water marina and head out on your boat for a sunset cruise. Boat slips are convenient and affordable, making every day boating a reality. Residents enjoy a heated waterfront pool and a vibrant, active community—ideal for seasonal snowbirds seeking a winter retreat or those who prefer the ease of year round coastal living. Guest parking is conveniently located behind the villa and at the marina. EXTRA BONUS: A seasonal tenant is in place January–April, offering an attractive opportunity to offset carrying costs. Inquire for details and plan your visit—this one is easy to love!

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

BACK AND BETTER THAN EVER! This completely renovated, turnkey furnished 2BR/2BA villa in the coveted 55+ Spanish Main Yacht Club returns to market with a NEW ROOF and NEW HVAC, both with transferable warranties. A prior appraisal documents 1,393 SF of above grade living space, offering more room than previously reflected in the MLS. The home also features impact windows and doors, adding peace of mind and year round durability as well as a full house water filtration system. Step outside to your spacious private patio—perfect for grilling, relaxing, and enjoying the coastal breeze. From there, take a short stroll across the road to your deeded Gulf beach access, or walk just a few steps to the deep water marina and head out on your boat for a sunset cruise. Boat slips are convenient and affordable, making every day boating a reality. Residents enjoy a heated waterfront pool and a vibrant, active community—ideal for seasonal snowbirds seeking a winter retreat or those who prefer the ease of year round coastal living. Guest parking is conveniently located behind the villa and at the marina. EXTRA BONUS: A seasonal tenant is in place January–April, offering an attractive opportunity to offset carrying costs. Inquire for details and plan your visit—this one is easy to love!

546 Spanish Drive S, Longboat Key

$5,295,000

Set against the luminous backdrop of prestigious Longboat Key, this newly built residence offers a quietly sophisticated interpretation of island living. Ideally situated just across from the beach, the home is framed by glimpses of the water, while its considered architecture and refined interiors create an atmosphere of understated luxury. Here, contemporary design meets the effortless beauty of coastal life, creating a private retreat that feels polished yet deeply connected to its surroundings. Lush, mature landscaping envelops the property in a verdant embrace, ensuring privacy and a sense of tranquility that makes every moment feel like a serene escape. Sunlight streams through expansive windows, filling every room with natural light and creating an inviting atmosphere. Featuring a 3-car garage with dual driveways and convenient elevator access to all levels, the impressive 4,361-square-foot residence, with a total of 6,527 square feet under roof, is thoughtfully designed for both grand entertaining and intimate daily living. An attached poolside casita boasts a dedicated entrance with elegant French doors, a bedroom with a walk-in closet, a kitchenette, a full bath, and a covered lanai. Every detail has been carefully considered to ensure comfort and versatility, with 4 additional bedrooms, 3.5 baths, a quiet study, an upper-level lobby and exercise room, plus laundry rooms on both floors for ultimate convenience. Step inside through grand iron-and-glass double doors to a dramatic foyer and gallery, where a stunning glass-enclosed wine room is an artistic focal point. High ceilings amplify the airy, light-filled ambiance throughout, creating a sense of openness and grandeur that is both welcoming and awe-inspiring. The screened pool area features a rejuvenating spa, tranquil waterfall, captivating fire feature, and an expansive covered lanai with a built-in cabana bar, professional-grade grilling station, serving-island buffet, generous dining space, and a comfortable outdoor living area. Inside, the great room impresses with a sleek linear fireplace, beautifully designed beamed ceiling, and massive glass sliders that open wide to the lush poolside retreat. The high-end island kitchen is a connoisseur's dream, equipped with premium appliances and a wall of windows framing vibrant tropical views. Adjacent spaces include a pool bath, a large walk-in pantry, a laundry room with a sink and ample storage, and a convenient elevator valet area. The study is a private haven, featuring a custom ceiling, two full walls of glass with panoramic views, and a VIP ensuite off the foyer with a secluded balcony for peaceful moments. Distinctive designer light fixtures and dazzling chandeliers lend the space glamour and sophistication. Upstairs, the second floor includes elevator access, a lobby, an exercise room, two bedrooms, and a full bath. A dramatic bridge overlooking the great room leads to the magnificent primary suite, with intricate ceiling details, a large expanse of windows, a private water closet, a spa-like bath with dual vanities, a freestanding soaking tub, a grand full-height glass shower, and a customized wardrobe room. Completed in December 2025 by custom luxury builder John Cannon Homes, this exceptional residence is far more than a stylish, elegant home with gracious open living—it is a sanctuary, a retreat, and an invitation to savor the very best of the coastal lifestyle.

5 Beds ⋅ 5 Baths ⋅ Triton Cove SubDv. ⋅ 34228 Zip Code

Set against the luminous backdrop of prestigious Longboat Key, this newly built residence offers a quietly sophisticated interpretation of island living. Ideally situated just across from the beach, the home is framed by glimpses of the water, while its considered architecture and refined interiors create an atmosphere of understated luxury. Here, contemporary design meets the effortless beauty of coastal life, creating a private retreat that feels polished yet deeply connected to its surroundings. Lush, mature landscaping envelops the property in a verdant embrace, ensuring privacy and a sense of tranquility that makes every moment feel like a serene escape. Sunlight streams through expansive windows, filling every room with natural light and creating an inviting atmosphere. Featuring a 3-car garage with dual driveways and convenient elevator access to all levels, the impressive 4,361-square-foot residence, with a total of 6,527 square feet under roof, is thoughtfully designed for both grand entertaining and intimate daily living. An attached poolside casita boasts a dedicated entrance with elegant French doors, a bedroom with a walk-in closet, a kitchenette, a full bath, and a covered lanai. Every detail has been carefully considered to ensure comfort and versatility, with 4 additional bedrooms, 3.5 baths, a quiet study, an upper-level lobby and exercise room, plus laundry rooms on both floors for ultimate convenience. Step inside through grand iron-and-glass double doors to a dramatic foyer and gallery, where a stunning glass-enclosed wine room is an artistic focal point. High ceilings amplify the airy, light-filled ambiance throughout, creating a sense of openness and grandeur that is both welcoming and awe-inspiring. The screened pool area features a rejuvenating spa, tranquil waterfall, captivating fire feature, and an expansive covered lanai with a built-in cabana bar, professional-grade grilling station, serving-island buffet, generous dining space, and a comfortable outdoor living area. Inside, the great room impresses with a sleek linear fireplace, beautifully designed beamed ceiling, and massive glass sliders that open wide to the lush poolside retreat. The high-end island kitchen is a connoisseur's dream, equipped with premium appliances and a wall of windows framing vibrant tropical views. Adjacent spaces include a pool bath, a large walk-in pantry, a laundry room with a sink and ample storage, and a convenient elevator valet area. The study is a private haven, featuring a custom ceiling, two full walls of glass with panoramic views, and a VIP ensuite off the foyer with a secluded balcony for peaceful moments. Distinctive designer light fixtures and dazzling chandeliers lend the space glamour and sophistication. Upstairs, the second floor includes elevator access, a lobby, an exercise room, two bedrooms, and a full bath. A dramatic bridge overlooking the great room leads to the magnificent primary suite, with intricate ceiling details, a large expanse of windows, a private water closet, a spa-like bath with dual vanities, a freestanding soaking tub, a grand full-height glass shower, and a customized wardrobe room. Completed in December 2025 by custom luxury builder John Cannon Homes, this exceptional residence is far more than a stylish, elegant home with gracious open living—it is a sanctuary, a retreat, and an invitation to savor the very best of the coastal lifestyle.

3100 Gulf Of Mexico Drive, Longboat Key

$3,495,000

Beyond the gates of Bayou Hammock, where just 11 residences share one of north Longboat Key’s most private waterfront settings, a true coastal retreat awaits. Arrive through one of two private gated entrances, where refreshed tropical landscaping and a charming butterfly garden welcome you home. Set on an expansive 0.83-acre lot with approximately 150 feet of direct canal frontage, the property offers sailboat water and room to accommodate vessels up to approximately 70 feet. Thoughtfully reimagined by the current owner, the beautifully renovated bungalow blends timeless Old Florida character with modern comfort. The 3-bedroom, 3-bathroom main residence is complemented by an attached guest casita with its own bedroom and bathroom, creating a total of 4 bedrooms, 4 bathrooms, and approximately 2,600 square feet of air-conditioned living space. Distinctive keystone accents will continue to develop a rich, natural patina in the coastal climate, while impact-rated windows and doors, a new standing-seam metal roof, and an attached one-car garage provide lasting value and peace of mind. Life here unfolds outdoors. Begin the morning beside the pool, rinse off beneath the outdoor shower after an afternoon on the water, or step onto the brand-new dock and set out from one of two new 10,000-pound boat lifts. Spend the day boating, fishing, and exploring the surrounding waterways before returning to your own peaceful hideaway. Just moments from the beaches, dining, and relaxed charm of north Longboat Key and nearby Anna Maria Island, this exceptional property is also zoned for Anna Maria Elementary School. More than a waterfront home, it is a private island sanctuary offering rare space, remarkable boating access, and an unhurried way of life.

4 Beds ⋅ 4 Baths ⋅ Acreage SubDv. ⋅ 34228 Zip Code

Beyond the gates of Bayou Hammock, where just 11 residences share one of north Longboat Key’s most private waterfront settings, a true coastal retreat awaits. Arrive through one of two private gated entrances, where refreshed tropical landscaping and a charming butterfly garden welcome you home. Set on an expansive 0.83-acre lot with approximately 150 feet of direct canal frontage, the property offers sailboat water and room to accommodate vessels up to approximately 70 feet. Thoughtfully reimagined by the current owner, the beautifully renovated bungalow blends timeless Old Florida character with modern comfort. The 3-bedroom, 3-bathroom main residence is complemented by an attached guest casita with its own bedroom and bathroom, creating a total of 4 bedrooms, 4 bathrooms, and approximately 2,600 square feet of air-conditioned living space. Distinctive keystone accents will continue to develop a rich, natural patina in the coastal climate, while impact-rated windows and doors, a new standing-seam metal roof, and an attached one-car garage provide lasting value and peace of mind. Life here unfolds outdoors. Begin the morning beside the pool, rinse off beneath the outdoor shower after an afternoon on the water, or step onto the brand-new dock and set out from one of two new 10,000-pound boat lifts. Spend the day boating, fishing, and exploring the surrounding waterways before returning to your own peaceful hideaway. Just moments from the beaches, dining, and relaxed charm of north Longboat Key and nearby Anna Maria Island, this exceptional property is also zoned for Anna Maria Elementary School. More than a waterfront home, it is a private island sanctuary offering rare space, remarkable boating access, and an unhurried way of life.

6561 Bayou Hammock Road, Longboat Key

1445 Gulf Of Mexico Drive Unit 101, Longboat Key

$1,090,000

Step into this highly desirable corner residence featuring three bedrooms, three full baths, and a 36’ x 11’ sunroom at The Players Club. Unique to this residence is a private garage, offering rare security and convenience plus an additional covered under-building parking space. You’ll immediately be drawn to the impressive 31’ balcony, offering sweeping views of the resort-style pool, lush, landscaped grounds, and breathtaking sunsets over the Gulf of Mexico. The outdoor space is perfect for alfresco dining, entertaining friends, or simply enjoying the tranquil Gulf breezes. An open, white eat-in kitchen is designed with custom cabinetry and extra storage that flows seamlessly into the main living and dining areas. Just off the kitchen, French doors open to a generous multipurpose sunroom that can serve as a home office, reading retreat, casual lounge, or even a fourth bedroom for guests. The primary bedroom, a private sanctuary with an en-suite bath offers a soaking tub, separate glass-enclosed shower, dual vanities, and a fitted walk-in closet. A second bedroom functions as an additional master with a fitted walk-in closet and en-suite bath with dual sinks. A true third bedroom with two separate fitted closets and an adjacent full bathroom adds flexibility for additional guests. Set on 11 acres of beachfront with 560 feet of Gulf frontage, The Players Club offers abundant green space, four Har-Tru tennis courts, a 70-foot heated saltwater pool, spa, fitness center, renovated clubhouse with catering kitchen, outdoor grilling areas, putting green, on-site management, and fully funded reserves and is located Just minutes from St. Armands Circle, downtown Longboat Key, and the Longboat Key Club - with championship golf, premier tennis, and a deep-water marina. One of the largest floor plans available in the community, this residence blends privacy, convenience, and resort-style beachfront living. Offered partially furnished.

3 Beds ⋅ 3 Baths ⋅ Players Club SubDv. ⋅ 34228 Zip Code

Step into this highly desirable corner residence featuring three bedrooms, three full baths, and a 36’ x 11’ sunroom at The Players Club. Unique to this residence is a private garage, offering rare security and convenience plus an additional covered under-building parking space. You’ll immediately be drawn to the impressive 31’ balcony, offering sweeping views of the resort-style pool, lush, landscaped grounds, and breathtaking sunsets over the Gulf of Mexico. The outdoor space is perfect for alfresco dining, entertaining friends, or simply enjoying the tranquil Gulf breezes. An open, white eat-in kitchen is designed with custom cabinetry and extra storage that flows seamlessly into the main living and dining areas. Just off the kitchen, French doors open to a generous multipurpose sunroom that can serve as a home office, reading retreat, casual lounge, or even a fourth bedroom for guests. The primary bedroom, a private sanctuary with an en-suite bath offers a soaking tub, separate glass-enclosed shower, dual vanities, and a fitted walk-in closet. A second bedroom functions as an additional master with a fitted walk-in closet and en-suite bath with dual sinks. A true third bedroom with two separate fitted closets and an adjacent full bathroom adds flexibility for additional guests. Set on 11 acres of beachfront with 560 feet of Gulf frontage, The Players Club offers abundant green space, four Har-Tru tennis courts, a 70-foot heated saltwater pool, spa, fitness center, renovated clubhouse with catering kitchen, outdoor grilling areas, putting green, on-site management, and fully funded reserves and is located Just minutes from St. Armands Circle, downtown Longboat Key, and the Longboat Key Club - with championship golf, premier tennis, and a deep-water marina. One of the largest floor plans available in the community, this residence blends privacy, convenience, and resort-style beachfront living. Offered partially furnished.

1445 Gulf Of Mexico Drive Unit 101, Longboat Key

4485 Gulf Of Mexico Drive Unit 402, Longboat Key

$345,678

Virtually Staged. Auction Property. Auction Property. This Beachfront Condominium will be sold at an Online Auction October 29 ~ November 4. 4485 GULF OF MEXICO DR, #402, LONGBOAT KEY, FL. This is a 2 Bedroom, 2 Bathroom Condominium with stunning views of the brilliant Gulf from every room and immediate beach access on Longboat Key. Arbomar Owners enjoy a heated beachfront pool, fitness center, and a welcoming well-maintained community with private coded access and an elevator. All special assessments will be paid in full by the seller at closing, eliminating future capital expense concerns for the buyer. The residence features a bright, open layout designed to capture stunning water views and coastal breezes. Significant recent improvements provide exceptional value and peace of mind, including a new roof, new balconies and walkways with diamond coating, updated carports, and new doors and impact-rated windows throughout the community. The pool has just been resurfaced. Inside, the home is ready for you to add your own flair. Ideal for full-time living, a seasonal retreat, or an income-producing beach getaway. This condo has a community washer and dryer just outside the front door, and also has a space where one could be installed inside. There are also storm shutters on the balcony for extra security. It comes with one dedicated covered parking spot and extra storage space downstairs. The amenities includes 24 hour security, pavered parking and entrance, elevators, a glistening resort style swimming pool, recreation clubhouse, shuffleboard, and fitness center. Perfectly positioned on Longboat Key, Arbomar is just minutes from St. Armands Circle, Sarasota’s dining and cultural attractions and world-class golf, and just a short trip to the Sarasota International Airport. Experience the luxury of Florida living with panoramic Gulf views and stunning sunsets every day. This building has cell phone towers on the roof that generate significant income for the association. With low maintenance fees and a great rental policy. The Milestone study and SIRS are completed and any past fees will be brought up to date at closing. This sale will come with a Warranty Deed ensuring that all taxes and condominium fees are current. This property will only be sold at Auction. ANY price in any listing or advertisement is for reference only, the selling price will be determined at auction. There is NO starting bid, you may bid any amount.

2 Beds ⋅ 2 Baths ⋅ Arbomar Apts SubDv. ⋅ 34228 Zip Code

Virtually Staged. Auction Property. Auction Property. This Beachfront Condominium will be sold at an Online Auction October 29 ~ November 4. 4485 GULF OF MEXICO DR, #402, LONGBOAT KEY, FL. This is a 2 Bedroom, 2 Bathroom Condominium with stunning views of the brilliant Gulf from every room and immediate beach access on Longboat Key. Arbomar Owners enjoy a heated beachfront pool, fitness center, and a welcoming well-maintained community with private coded access and an elevator. All special assessments will be paid in full by the seller at closing, eliminating future capital expense concerns for the buyer. The residence features a bright, open layout designed to capture stunning water views and coastal breezes. Significant recent improvements provide exceptional value and peace of mind, including a new roof, new balconies and walkways with diamond coating, updated carports, and new doors and impact-rated windows throughout the community. The pool has just been resurfaced. Inside, the home is ready for you to add your own flair. Ideal for full-time living, a seasonal retreat, or an income-producing beach getaway. This condo has a community washer and dryer just outside the front door, and also has a space where one could be installed inside. There are also storm shutters on the balcony for extra security. It comes with one dedicated covered parking spot and extra storage space downstairs. The amenities includes 24 hour security, pavered parking and entrance, elevators, a glistening resort style swimming pool, recreation clubhouse, shuffleboard, and fitness center. Perfectly positioned on Longboat Key, Arbomar is just minutes from St. Armands Circle, Sarasota’s dining and cultural attractions and world-class golf, and just a short trip to the Sarasota International Airport. Experience the luxury of Florida living with panoramic Gulf views and stunning sunsets every day. This building has cell phone towers on the roof that generate significant income for the association. With low maintenance fees and a great rental policy. The Milestone study and SIRS are completed and any past fees will be brought up to date at closing. This sale will come with a Warranty Deed ensuring that all taxes and condominium fees are current. This property will only be sold at Auction. ANY price in any listing or advertisement is for reference only, the selling price will be determined at auction. There is NO starting bid, you may bid any amount.

4485 Gulf Of Mexico Drive Unit 402, Longboat Key

3808 Gulf Of Mexico Drive Unit E412, Longboat Key

$1,175,000

Rarely available penthouse living at Beach Harbor Club pairs sweeping Sarasota Bay views with deeded access to the white sands of the Gulf of Mexico. Set on the top floor of Building E, Residence #E412 is an exceptionally spacious three-bedroom, three-bath retreat offering more than 2,500 square feet, captivating water views from nearly every room and the relaxed indoor-outdoor lifestyle that makes Longboat Key so desirable. This residence also includes two premium covered parking spaces. From the moment you arrive, the water takes center stage. A private screened front patio creates an inviting outdoor perch overlooking the bay, while inside, an expansive, light-filled floor plan unfolds through generous living, dining and family spaces. Walls of glass frame the sparkling bay, surrounding tropical landscape and boating activity below, creating a constant connection to the waterfront setting. The oversized living room flows naturally into the enclosed bayfront terrace, now incorporated as a comfortable family room for additional year-round living space. Impact-rated sliding glass doors open to a Juliet balcony, inviting refreshing bay breezes inside while preserving the protection and comfort of an enclosed space. It is an ideal setting for morning coffee, reading, entertaining or simply watching the ever-changing colors of the water. Designed for both everyday living and entertaining, the formal dining room is surrounded by windows and enjoys beautiful bay views. The adjacent eat-in kitchen, renovated in 2018, features abundant cabinetry and workspace, a breakfast nook and its own picturesque outlook across the water. Three generously sized bedrooms are arranged in a desirable split plan, providing privacy for owners and overnight guests. The spacious primary suite is positioned to take advantage of the waterfront setting and includes a sitting area and an updated en-suite bath renovated in 2023. The additional bedroom suites offer exceptional flexibility for visiting family, guests or a home office. Beyond the residence, Beach Harbor Club delivers the quintessential Longboat Key lifestyle from bay to beach. Residents enjoy a bayfront clubhouse with social room, bar and catering kitchen, library, fitness center, heated swimming pool, Tiki hut and barbecue area, shuffleboard, car wash station, fish-cleaning station and outdoor shower. Boaters and paddlers will especially appreciate Beach Harbor Club's on-site marina, where assigned boat slips and kayak storage racks are available on a first-come basis. Just across Gulf of Mexico Drive, the community's deeded Gulf beach access puts the turquoise waters and soft sands of Longboat Key only moments from home—offering the rare opportunity to spend the morning boating on Sarasota Bay and the afternoon along the Gulf. Ideally positioned on the southern end of Longboat Key, #E412 is convenient to the boutiques, restaurants and cafés of St. Armands Circle, while Downtown Sarasota is just beyond the Ringling Bridge for acclaimed dining, galleries, theaters, the Sarasota Opera, Marina Jack and the city's celebrated arts and cultural scene. Longboat Key's waterfront restaurants, golf, tennis, parks and miles of shoreline are also close at hand.

3 Beds ⋅ 3 Baths ⋅ Beach Harbor Club SubDv. ⋅ 34228 Zip Code

Rarely available penthouse living at Beach Harbor Club pairs sweeping Sarasota Bay views with deeded access to the white sands of the Gulf of Mexico. Set on the top floor of Building E, Residence #E412 is an exceptionally spacious three-bedroom, three-bath retreat offering more than 2,500 square feet, captivating water views from nearly every room and the relaxed indoor-outdoor lifestyle that makes Longboat Key so desirable. This residence also includes two premium covered parking spaces. From the moment you arrive, the water takes center stage. A private screened front patio creates an inviting outdoor perch overlooking the bay, while inside, an expansive, light-filled floor plan unfolds through generous living, dining and family spaces. Walls of glass frame the sparkling bay, surrounding tropical landscape and boating activity below, creating a constant connection to the waterfront setting. The oversized living room flows naturally into the enclosed bayfront terrace, now incorporated as a comfortable family room for additional year-round living space. Impact-rated sliding glass doors open to a Juliet balcony, inviting refreshing bay breezes inside while preserving the protection and comfort of an enclosed space. It is an ideal setting for morning coffee, reading, entertaining or simply watching the ever-changing colors of the water. Designed for both everyday living and entertaining, the formal dining room is surrounded by windows and enjoys beautiful bay views. The adjacent eat-in kitchen, renovated in 2018, features abundant cabinetry and workspace, a breakfast nook and its own picturesque outlook across the water. Three generously sized bedrooms are arranged in a desirable split plan, providing privacy for owners and overnight guests. The spacious primary suite is positioned to take advantage of the waterfront setting and includes a sitting area and an updated en-suite bath renovated in 2023. The additional bedroom suites offer exceptional flexibility for visiting family, guests or a home office. Beyond the residence, Beach Harbor Club delivers the quintessential Longboat Key lifestyle from bay to beach. Residents enjoy a bayfront clubhouse with social room, bar and catering kitchen, library, fitness center, heated swimming pool, Tiki hut and barbecue area, shuffleboard, car wash station, fish-cleaning station and outdoor shower. Boaters and paddlers will especially appreciate Beach Harbor Club's on-site marina, where assigned boat slips and kayak storage racks are available on a first-come basis. Just across Gulf of Mexico Drive, the community's deeded Gulf beach access puts the turquoise waters and soft sands of Longboat Key only moments from home—offering the rare opportunity to spend the morning boating on Sarasota Bay and the afternoon along the Gulf. Ideally positioned on the southern end of Longboat Key, #E412 is convenient to the boutiques, restaurants and cafés of St. Armands Circle, while Downtown Sarasota is just beyond the Ringling Bridge for acclaimed dining, galleries, theaters, the Sarasota Opera, Marina Jack and the city's celebrated arts and cultural scene. Longboat Key's waterfront restaurants, golf, tennis, parks and miles of shoreline are also close at hand.

3808 Gulf Of Mexico Drive Unit E412, Longboat Key

4525 Gulf Of Mexico Drive Unit 204, Longboat Key

$1,125,000

Direct Gulf-front living, uninterrupted beach views and spectacular sunsets define this furnished retreat at The Castillian on Longboat Key. Positioned in the South Building, Residence #204 offers a front-row perspective of the Gulf of Mexico, with expansive water views from nearly every room. Thoughtfully maintained and updated, this two-bedroom residence offers 1,362 square feet of interior living space, including an enclosed Gulf-front terrace that creates a comfortable extension of the residence. From the moment you enter, the Gulf becomes the focal point. A light-filled, open living and dining area leads directly to the enclosed terrace, where floor-to-ceiling glass frames turquoise water, the natural dune landscape and the beach beyond. Impact sliding glass doors open to welcome refreshing Gulf breezes, creating a versatile space for enjoying the ever-changing coastal scenery and everyday living. The east-facing eat-in kitchen, updated in 2017, combines functionality with a fresh coastal aesthetic. Quartz countertops, a breakfast bar, stainless steel appliances and shaker-style cabinetry complement the generous workspace, while a convenient laundry closet adds everyday practicality. The kitchen connects naturally to the living and dining areas, creating an easy flow for entertaining. A split-bedroom floor plan provides privacy for owners and guests. The Gulf-facing primary suite offers beautiful water views, a walk-in closet and an en-suite bath updated in 2017 with quartz finishes and a glass-enclosed shower. The guest bedroom is comfortably separated from the primary suite and is served by a similarly updated second bath. Offered turnkey furnished, the residence is ready for immediate enjoyment as a full-time island home or seasonal getaway. Additional conveniences include deeded under-building parking and a separate storage unit. Beyond the residence, The Castillian offers the intimate atmosphere of a 60-residence beachfront community, with two buildings overlooking the Gulf. Its beautifully maintained grounds and collection of amenities encourage an easygoing coastal lifestyle. Spend afternoons beside the heated Gulfside swimming pool, unwind in the hot tub or gather with friends at the clubhouse and outdoor grilling area. Tennis, kayak storage and opportunities for walking and biking add to the appeal, while more than 700 feet of beachfront places Longboat Key’s soft sand and sparkling Gulf waters just steps from your front door. The community is pet-friendly, subject to association restrictions. The Castillian’s central Longboat Key location also provides convenient access to the island’s waterfront restaurants, golf, tennis and marinas. To the south, St. Armands Circle offers boutique shopping, restaurants and cafés, while Downtown Sarasota is home to acclaimed dining, galleries, theaters, Sarasota Opera, Marie Selby Botanical Gardens and the scenic Bayfront. To the north, Anna Maria Island and the charming coastal communities of Manatee County offer additional opportunities for exploring Southwest Florida.

2 Beds ⋅ 2 Baths ⋅ Castillian The SubDv. ⋅ 34228 Zip Code

Direct Gulf-front living, uninterrupted beach views and spectacular sunsets define this furnished retreat at The Castillian on Longboat Key. Positioned in the South Building, Residence #204 offers a front-row perspective of the Gulf of Mexico, with expansive water views from nearly every room. Thoughtfully maintained and updated, this two-bedroom residence offers 1,362 square feet of interior living space, including an enclosed Gulf-front terrace that creates a comfortable extension of the residence. From the moment you enter, the Gulf becomes the focal point. A light-filled, open living and dining area leads directly to the enclosed terrace, where floor-to-ceiling glass frames turquoise water, the natural dune landscape and the beach beyond. Impact sliding glass doors open to welcome refreshing Gulf breezes, creating a versatile space for enjoying the ever-changing coastal scenery and everyday living. The east-facing eat-in kitchen, updated in 2017, combines functionality with a fresh coastal aesthetic. Quartz countertops, a breakfast bar, stainless steel appliances and shaker-style cabinetry complement the generous workspace, while a convenient laundry closet adds everyday practicality. The kitchen connects naturally to the living and dining areas, creating an easy flow for entertaining. A split-bedroom floor plan provides privacy for owners and guests. The Gulf-facing primary suite offers beautiful water views, a walk-in closet and an en-suite bath updated in 2017 with quartz finishes and a glass-enclosed shower. The guest bedroom is comfortably separated from the primary suite and is served by a similarly updated second bath. Offered turnkey furnished, the residence is ready for immediate enjoyment as a full-time island home or seasonal getaway. Additional conveniences include deeded under-building parking and a separate storage unit. Beyond the residence, The Castillian offers the intimate atmosphere of a 60-residence beachfront community, with two buildings overlooking the Gulf. Its beautifully maintained grounds and collection of amenities encourage an easygoing coastal lifestyle. Spend afternoons beside the heated Gulfside swimming pool, unwind in the hot tub or gather with friends at the clubhouse and outdoor grilling area. Tennis, kayak storage and opportunities for walking and biking add to the appeal, while more than 700 feet of beachfront places Longboat Key’s soft sand and sparkling Gulf waters just steps from your front door. The community is pet-friendly, subject to association restrictions. The Castillian’s central Longboat Key location also provides convenient access to the island’s waterfront restaurants, golf, tennis and marinas. To the south, St. Armands Circle offers boutique shopping, restaurants and cafés, while Downtown Sarasota is home to acclaimed dining, galleries, theaters, Sarasota Opera, Marie Selby Botanical Gardens and the scenic Bayfront. To the north, Anna Maria Island and the charming coastal communities of Manatee County offer additional opportunities for exploring Southwest Florida.

4525 Gulf Of Mexico Drive Unit 204, Longboat Key

$2,100,000

Virtually Staged. Tucked within the highly sought after Queens Harbour enclave of Bay Isles, this exceptional residence captures the effortless elegance and relaxed sophistication of the Longboat Key lifestyle. Queens Harbour offers the rare combination of single-family living with a low-maintenance lifestyle, including landscaping, irrigation, and exterior painting. Grand double entry doors open to nearly 3,000 square feet of beautifully refreshed interiors, where soaring 12- to 15-foot ceilings, abundant natural light, serene water views, and refined architectural details create an immediate sense of space and tranquility. Newly installed wood-look porcelain tile flows throughout the living and dining rooms, den, and first-floor bedrooms, bringing warmth and continuity to the home. At the heart of the residence, the newly renovated kitchen pairs sophisticated design with exceptional functionality. Quartz countertops, a dramatic waterfall island, second prep sink, new backsplash, and stainless steel appliances create an inviting space for cooking and entertaining. An adjoining breakfast nook is framed by a bay window overlooking the pool and lake. The thoughtfully designed split floor plan features three private en-suite bedrooms, a powder room, and an elegant den or office with custom cabinetry that may also serve as a fourth bedroom. The first-floor owner’s suite enjoys direct lanai access and tranquil lake views, complemented by a spa-inspired bath with dual vanities, soaking tub, and spacious walk-in shower. A second en-suite bedroom on the main level provides privacy and comfort for guests. The upper level features an additional en-suite bedroom and flexible living area, creating a secluded retreat ideal for guests, extended stays, or multigenerational living. Outdoors, the expansive screened lanai embraces the home’s peaceful waterfront setting. A heated pool and spa overlook the lake and fountain, while a generous covered sitting area with tongue-and-groove ceiling and coordinating accent wall provides an inviting setting for entertaining or relaxing. A 2023 tile roof adds to the home’s thoughtful updates and long-term appeal. Ownership in Bay Isles includes access to the private Bay Isles Beach Club and its pristine Gulf shoreline. Optional membership to the Longboat Key Club offers golf, tennis, dining, resort amenities, and access to Harbourside Marina. Ideally situated in the heart of Longboat Key, the home is convenient to the shops and everyday amenities of Bay Isles, with St. Armands Circle and downtown Sarasota’s acclaimed dining, arts, and cultural offerings just a scenic drive away. Boating, kayaking, fishing, waterfront dining, and some of Florida’s most beautiful beaches are all within easy reach. A refined island residence offering the privacy of a single-family home, the ease of low-maintenance living, and the exceptional lifestyle that defines Bay Isles and Longboat Key.

3 Beds ⋅ 4 Baths ⋅ Queens Harbour (F/K/A Manchester Bay) SubDv. ⋅ 34228 Zip Code

Virtually Staged. Tucked within the highly sought after Queens Harbour enclave of Bay Isles, this exceptional residence captures the effortless elegance and relaxed sophistication of the Longboat Key lifestyle. Queens Harbour offers the rare combination of single-family living with a low-maintenance lifestyle, including landscaping, irrigation, and exterior painting. Grand double entry doors open to nearly 3,000 square feet of beautifully refreshed interiors, where soaring 12- to 15-foot ceilings, abundant natural light, serene water views, and refined architectural details create an immediate sense of space and tranquility. Newly installed wood-look porcelain tile flows throughout the living and dining rooms, den, and first-floor bedrooms, bringing warmth and continuity to the home. At the heart of the residence, the newly renovated kitchen pairs sophisticated design with exceptional functionality. Quartz countertops, a dramatic waterfall island, second prep sink, new backsplash, and stainless steel appliances create an inviting space for cooking and entertaining. An adjoining breakfast nook is framed by a bay window overlooking the pool and lake. The thoughtfully designed split floor plan features three private en-suite bedrooms, a powder room, and an elegant den or office with custom cabinetry that may also serve as a fourth bedroom. The first-floor owner’s suite enjoys direct lanai access and tranquil lake views, complemented by a spa-inspired bath with dual vanities, soaking tub, and spacious walk-in shower. A second en-suite bedroom on the main level provides privacy and comfort for guests. The upper level features an additional en-suite bedroom and flexible living area, creating a secluded retreat ideal for guests, extended stays, or multigenerational living. Outdoors, the expansive screened lanai embraces the home’s peaceful waterfront setting. A heated pool and spa overlook the lake and fountain, while a generous covered sitting area with tongue-and-groove ceiling and coordinating accent wall provides an inviting setting for entertaining or relaxing. A 2023 tile roof adds to the home’s thoughtful updates and long-term appeal. Ownership in Bay Isles includes access to the private Bay Isles Beach Club and its pristine Gulf shoreline. Optional membership to the Longboat Key Club offers golf, tennis, dining, resort amenities, and access to Harbourside Marina. Ideally situated in the heart of Longboat Key, the home is convenient to the shops and everyday amenities of Bay Isles, with St. Armands Circle and downtown Sarasota’s acclaimed dining, arts, and cultural offerings just a scenic drive away. Boating, kayaking, fishing, waterfront dining, and some of Florida’s most beautiful beaches are all within easy reach. A refined island residence offering the privacy of a single-family home, the ease of low-maintenance living, and the exceptional lifestyle that defines Bay Isles and Longboat Key.

3617 Fair Oaks Place, Longboat Key

$4,699,999

Virtually Staged. Brand-new custom construction in Bay Isles? This is it. Introducing an exceptional new residence in one of Longboat Key’s most coveted gated communities. Designed for effortless coastal living, this sophisticated home combines coastal contemporary architecture, elevated construction above current flood requirements, an oversized homesite, and beautifully curated tropical gardens creating a private, resort-like setting. Inside, exceptional craftsmanship is evident throughout. The chef’s kitchen features a quartzite island, brass-strapped custom hood, panel-front refrigeration with fridge, freezer, and wine tower, vaulted beamed ceiling with concealed cove lighting and Thermador appliances. Designed to be a true masterpiece sure to impress. The great room showcases a walnut-clad fireplace wall, custom built-ins, wide-plank engineered wood floors, backlit tray ceiling, and expansive sliding glass doors opening to the outdoor living areas. The primary suite overlooking the tranquil back yard, offers a spa-inspired bath with freestanding soaking tub, rain shower, dual vanity, and customized walk-in closets. This floor plan also allows for an additional first floor primary or guest bedroom suite with custom full bath. The second floor offers three additional bedroom suites providing beautifully appointed accommodations for family and guests. Outdoors, the home becomes its own private resort. A covered lanai opens to a heated saltwater pool and spa, beautifully landscaped backyard with its own private putting green, and stainless-steel outdoor kitchen with built-in gas grill—an exceptional setting for entertaining, relaxing, or perfecting your short game at home. The location completes the experience. Set in south Longboat Key, the home is within walking distance of the Longboat Key Club, with golf, tennis, marina, dining, and beach club amenities nearby. Bay Isles residents also enjoy access to their own private Gulf-front Beach Club with powder-soft sand and spectacular Gulf waters. The Beach Club also provides bbq grills, pavilion, locker rooms, storage, and ice machine. New construction, exceptional design and quality, private beach access, and one of Longboat Key’s premier locations—this home offers a rare opportunity to enjoy the Bay Isles lifestyle from day one. Close to Sarasota International Airport, downtown dining and entertainment, and everything wonderful offered by the beloved St Armands Circle.

5 Beds ⋅ 5 Baths ⋅ Bay Isles SubDv. ⋅ 34228 Zip Code

Virtually Staged. Brand-new custom construction in Bay Isles? This is it. Introducing an exceptional new residence in one of Longboat Key’s most coveted gated communities. Designed for effortless coastal living, this sophisticated home combines coastal contemporary architecture, elevated construction above current flood requirements, an oversized homesite, and beautifully curated tropical gardens creating a private, resort-like setting. Inside, exceptional craftsmanship is evident throughout. The chef’s kitchen features a quartzite island, brass-strapped custom hood, panel-front refrigeration with fridge, freezer, and wine tower, vaulted beamed ceiling with concealed cove lighting and Thermador appliances. Designed to be a true masterpiece sure to impress. The great room showcases a walnut-clad fireplace wall, custom built-ins, wide-plank engineered wood floors, backlit tray ceiling, and expansive sliding glass doors opening to the outdoor living areas. The primary suite overlooking the tranquil back yard, offers a spa-inspired bath with freestanding soaking tub, rain shower, dual vanity, and customized walk-in closets. This floor plan also allows for an additional first floor primary or guest bedroom suite with custom full bath. The second floor offers three additional bedroom suites providing beautifully appointed accommodations for family and guests. Outdoors, the home becomes its own private resort. A covered lanai opens to a heated saltwater pool and spa, beautifully landscaped backyard with its own private putting green, and stainless-steel outdoor kitchen with built-in gas grill—an exceptional setting for entertaining, relaxing, or perfecting your short game at home. The location completes the experience. Set in south Longboat Key, the home is within walking distance of the Longboat Key Club, with golf, tennis, marina, dining, and beach club amenities nearby. Bay Isles residents also enjoy access to their own private Gulf-front Beach Club with powder-soft sand and spectacular Gulf waters. The Beach Club also provides bbq grills, pavilion, locker rooms, storage, and ice machine. New construction, exceptional design and quality, private beach access, and one of Longboat Key’s premier locations—this home offers a rare opportunity to enjoy the Bay Isles lifestyle from day one. Close to Sarasota International Airport, downtown dining and entertainment, and everything wonderful offered by the beloved St Armands Circle.

3360 Bayou Sound, Longboat Key

$639,000

Second-home buyers and investment-minded buyers, take note. This beautifully furnished, turnkey residence at Cedars East on Longboat Key offers the rare combination of a polished coastal retreat, an established rental history, and meaningful upside potential. The home has generated approximately $50,000 in average annual rental payout revenue, after Airbnb and VRBO fees, providing a proven income history while maintaining the flexibility of up to 26 rental opportunities a year—an unusually flexible arrangement for Longboat Key. The owners have invested more than $130,000 in upgrades and improvements since 2021, creating a home that is not simply rental-ready, but thoughtfully maintained and continually enhanced. The current owners have created a home designed to deliver an exceptional guest experience. The sale includes the home's high-quality furnishings, top-of-the-line kitchenware—including All-Clad cookware—solid dishware, premium beach equipment and carefully selected décor. The result is reflected in the property's rental reputation, with more than 40, 5-Star Airbnb reviews from previous guests. Positioned near the front of Cedars East, the residence offers more convenient access to the Gulf beaches than many locations within the community and is next to the Longboat Key bike path. Inside, the 1,440-square-foot, two-bedroom, 2½-bath residence features an open living and dining area, a large garage, and a private, wooded outlook from the living room and lanai. The lush greenery creates a wonderfully private, almost treehouse-like setting—a peaceful contrast to the Gulf just moments away. Residents of Cedars East enjoy a resort-style setting with HOA amenities including the community pool, kayak and paddle board launch, fishing pier, cable, water, sewer, trash and pest control.Optional membership at the Cedars Tennis Resort & Club provides access to additional tennis, pickleball and fitness amenities. Whether you're looking for a beautifully finished Longboat Key retreat, a second home that can generate income, or a turnkey vacation property with an established rental history, this residence offers a compelling combination of lifestyle and flexibility. Come experience The Longboat Key Life.

2 Beds ⋅ 3 Baths ⋅ Cedars East SubDv. ⋅ 34228 Zip Code

Second-home buyers and investment-minded buyers, take note. This beautifully furnished, turnkey residence at Cedars East on Longboat Key offers the rare combination of a polished coastal retreat, an established rental history, and meaningful upside potential. The home has generated approximately $50,000 in average annual rental payout revenue, after Airbnb and VRBO fees, providing a proven income history while maintaining the flexibility of up to 26 rental opportunities a year—an unusually flexible arrangement for Longboat Key. The owners have invested more than $130,000 in upgrades and improvements since 2021, creating a home that is not simply rental-ready, but thoughtfully maintained and continually enhanced. The current owners have created a home designed to deliver an exceptional guest experience. The sale includes the home's high-quality furnishings, top-of-the-line kitchenware—including All-Clad cookware—solid dishware, premium beach equipment and carefully selected décor. The result is reflected in the property's rental reputation, with more than 40, 5-Star Airbnb reviews from previous guests. Positioned near the front of Cedars East, the residence offers more convenient access to the Gulf beaches than many locations within the community and is next to the Longboat Key bike path. Inside, the 1,440-square-foot, two-bedroom, 2½-bath residence features an open living and dining area, a large garage, and a private, wooded outlook from the living room and lanai. The lush greenery creates a wonderfully private, almost treehouse-like setting—a peaceful contrast to the Gulf just moments away. Residents of Cedars East enjoy a resort-style setting with HOA amenities including the community pool, kayak and paddle board launch, fishing pier, cable, water, sewer, trash and pest control.Optional membership at the Cedars Tennis Resort & Club provides access to additional tennis, pickleball and fitness amenities. Whether you're looking for a beautifully finished Longboat Key retreat, a second home that can generate income, or a turnkey vacation property with an established rental history, this residence offers a compelling combination of lifestyle and flexibility. Come experience The Longboat Key Life.

539 Forest Way Unit 539, Longboat Key

4600 Gulf Of Mexico Drive Unit 301, Longboat Key

$660,000

Welcome to Paradise! Fall in love with this turnkey furnished two- bedroom two bath End Unit condo! Relax and enjoy beautiful unobstructed views of Sarasota Bay from nearly every room in the house. The bright newly remodeled open concept kitchen has new cabinetry, quartz countertops and a large breakfast bar. You can even catch a sunset from the oversized westerly kitchen window. On the far side of the home is the master suite with an ensuite bath with a walk-in shower and dual sink vanity. The walk-in closet has built-in shelves and is large enough to accommodate the one-year-old stackable washer and dryer. The second bedroom has built in closets and drawers along with a built-in desk making it ideal for guests or a home office. Both bedrooms access the lanai that has an amazing view with its floor to ceiling windows. Additional features in the home include a whole house water filter, hurricane impact windows 2023, HVAC 2021, water heater 2022,microwave and range 2023 and a brand-new refrigerator. This home is extremely spacious and provides ample storage. There are two linen closets, three walk in closets and three sets of custom boudoir built-ins. There is also a ground level private storage room at your assigned under building parking space which happens to be located next to the Elevator. This condo is also located directly across from one of the community pools. Enjoy three beach access points (including one private), 26 acres of tropical surroundings including a 1/2 mile of nature trails, two heated pools, fitness center and sauna, clubhouse, tennis and pickleball courts, boat docks (waitlist) kayak launches, kayak storage and two marinas. You are also just minutes away from championship golf courses, restaurants, shopping, St. Armands Circle, Downtown Sarasota, and Anna Marie Island. This waterfront condo community and its great location has something for everyone to enjoy!

2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code

Welcome to Paradise! Fall in love with this turnkey furnished two- bedroom two bath End Unit condo! Relax and enjoy beautiful unobstructed views of Sarasota Bay from nearly every room in the house. The bright newly remodeled open concept kitchen has new cabinetry, quartz countertops and a large breakfast bar. You can even catch a sunset from the oversized westerly kitchen window. On the far side of the home is the master suite with an ensuite bath with a walk-in shower and dual sink vanity. The walk-in closet has built-in shelves and is large enough to accommodate the one-year-old stackable washer and dryer. The second bedroom has built in closets and drawers along with a built-in desk making it ideal for guests or a home office. Both bedrooms access the lanai that has an amazing view with its floor to ceiling windows. Additional features in the home include a whole house water filter, hurricane impact windows 2023, HVAC 2021, water heater 2022,microwave and range 2023 and a brand-new refrigerator. This home is extremely spacious and provides ample storage. There are two linen closets, three walk in closets and three sets of custom boudoir built-ins. There is also a ground level private storage room at your assigned under building parking space which happens to be located next to the Elevator. This condo is also located directly across from one of the community pools. Enjoy three beach access points (including one private), 26 acres of tropical surroundings including a 1/2 mile of nature trails, two heated pools, fitness center and sauna, clubhouse, tennis and pickleball courts, boat docks (waitlist) kayak launches, kayak storage and two marinas. You are also just minutes away from championship golf courses, restaurants, shopping, St. Armands Circle, Downtown Sarasota, and Anna Marie Island. This waterfront condo community and its great location has something for everyone to enjoy!

4600 Gulf Of Mexico Drive Unit 301, Longboat Key

$645,000

LONGBOAT KEY LIVING—FROM THE GULF TO THE BAY! Welcome to Bayport Beach & Tennis Club, where island living means having the beach, bay, tennis, kayaking, and resort-style amenities all within your own community. Tucked into a private setting surrounded by tropical landscaping, this 2-bedroom, 2-bath second-floor end unit offers something buyers will appreciate immediately—extra natural light, added privacy, and no one living above you. Inside, the residence feels comfortable and welcoming, with an open living and dining area and a split-bedroom design that gives owners and guests their own space. The kitchen and bathrooms have been updated, the windows are newer, and a full-size washer and dryer inside the condo adds everyday convenience. The primary suite includes a walk-in closet plus a bonus area that works beautifully as a small home office, reading nook, or additional storage space. Florida living continues outdoors with two separate spaces to enjoy. Start the day on the open-air deck or relax on the screened lanai surrounded by Bayport's lush landscaping. Covered parking, guest parking, multiple storage areas, and an owner's closet provide even more functionality. But what truly sets this property apart is Bayport itself. Spanning approximately 27 acres from the Gulf of Mexico to Sarasota Bay, this distinctive Longboat Key community offers approximately 1,200 feet of private Gulf beach access along with an impressive collection of amenities. Spend the day at the heated Junior Olympic-size pool, play a match on one of four Har-Tru tennis courts, work out in the fitness center, launch a kayak onto the bay, or head to the fishing pier. When it's time for the beach, chairs and umbrellas are available for residents to enjoy. Bayport's winding pathways, mature tropical landscaping, and low-density setting create a peaceful atmosphere that feels worlds away—yet you're conveniently located to the restaurants, shopping, and attractions of Longboat Key, St. Armands Circle, and Sarasota. Beach in the morning, bay in the afternoon, and a Gulf sunset to finish the day. Whether you're looking for a full-time residence or a Longboat Key getaway, this is an opportunity to enjoy the island lifestyle from one exceptional Gulf-to-Bay community.

2 Beds ⋅ 2 Baths ⋅ Bayport Bch & Ten SubDv. ⋅ 34228 Zip Code

LONGBOAT KEY LIVING—FROM THE GULF TO THE BAY! Welcome to Bayport Beach & Tennis Club, where island living means having the beach, bay, tennis, kayaking, and resort-style amenities all within your own community. Tucked into a private setting surrounded by tropical landscaping, this 2-bedroom, 2-bath second-floor end unit offers something buyers will appreciate immediately—extra natural light, added privacy, and no one living above you. Inside, the residence feels comfortable and welcoming, with an open living and dining area and a split-bedroom design that gives owners and guests their own space. The kitchen and bathrooms have been updated, the windows are newer, and a full-size washer and dryer inside the condo adds everyday convenience. The primary suite includes a walk-in closet plus a bonus area that works beautifully as a small home office, reading nook, or additional storage space. Florida living continues outdoors with two separate spaces to enjoy. Start the day on the open-air deck or relax on the screened lanai surrounded by Bayport's lush landscaping. Covered parking, guest parking, multiple storage areas, and an owner's closet provide even more functionality. But what truly sets this property apart is Bayport itself. Spanning approximately 27 acres from the Gulf of Mexico to Sarasota Bay, this distinctive Longboat Key community offers approximately 1,200 feet of private Gulf beach access along with an impressive collection of amenities. Spend the day at the heated Junior Olympic-size pool, play a match on one of four Har-Tru tennis courts, work out in the fitness center, launch a kayak onto the bay, or head to the fishing pier. When it's time for the beach, chairs and umbrellas are available for residents to enjoy. Bayport's winding pathways, mature tropical landscaping, and low-density setting create a peaceful atmosphere that feels worlds away—yet you're conveniently located to the restaurants, shopping, and attractions of Longboat Key, St. Armands Circle, and Sarasota. Beach in the morning, bay in the afternoon, and a Gulf sunset to finish the day. Whether you're looking for a full-time residence or a Longboat Key getaway, this is an opportunity to enjoy the island lifestyle from one exceptional Gulf-to-Bay community.

843 Bayport Way Unit 843, Longboat Key

3453 Gulf Of Mexico Drive Unit 237, Longboat Key

$495,000

This is it! a condo right on the beach and Gulf! Wake up in the morning, open the drapes, and there it is! Then, after a full day on the Key, sit back and watch a glorious sunset from your private balcony! This condo has been lovingly updated throughout, with everything you need to enjoy a weekend or the winter; when you're not using it, you may have the condo leased by onsite management, and enjoy an income year round- the best of both worlds! The pool and deck are a few steps away, and beach chairs are available to take right out to the water's edge. The Seahorse is in an ideal location on Longboat, with a Publix grocery, pickleball, tennis, boat rentals all about five minutes away. Go restaurant exploring on the Key-The Drydock, Chart House, Mar Vista, Shore and many others about 5 minutes away. Thinking about a round of golf? public golf courses are just 12 miles away. At the Seahorse Beach Resort, you have found your beach getaway, where you'll be warmly greeted.

1 Baths ⋅ Sea Horse Beach Resort SubDv. ⋅ 34228 Zip Code

This is it! a condo right on the beach and Gulf! Wake up in the morning, open the drapes, and there it is! Then, after a full day on the Key, sit back and watch a glorious sunset from your private balcony! This condo has been lovingly updated throughout, with everything you need to enjoy a weekend or the winter; when you're not using it, you may have the condo leased by onsite management, and enjoy an income year round- the best of both worlds! The pool and deck are a few steps away, and beach chairs are available to take right out to the water's edge. The Seahorse is in an ideal location on Longboat, with a Publix grocery, pickleball, tennis, boat rentals all about five minutes away. Go restaurant exploring on the Key-The Drydock, Chart House, Mar Vista, Shore and many others about 5 minutes away. Thinking about a round of golf? public golf courses are just 12 miles away. At the Seahorse Beach Resort, you have found your beach getaway, where you'll be warmly greeted.

3453 Gulf Of Mexico Drive Unit 237, Longboat Key

$599,900

Discover your ultimate island escape in this beautifully updated, fully furnished, and pet-friendly 2-bedroom, 2.5-bathroom townhome located within the desirable Cedars Tennis Resort & Club on Longboat Key. Set across a lush, village-like community enveloped by nature on the island's scenic north end, this property offers a rare combination of relaxed coastal living and an excellent short-term rental opportunity featuring a flexible two-week policy. Step inside to find a turnkey, coastal-chic interior highlighted by crisp shiplap accents, warm wood-style flooring, and elegant metallic hardware throughout. The updated kitchen features white shaker cabinetry, premium stone countertops, custom tile backsplash, and a breakfast bar with seating, all while offering a subtle peekaboo views of the glistening Gulf of Mexico. It flows seamlessly into a bright dining space framed by a shell-pendant chandelier and an inviting living room that opens through sliding glass doors to a private, screened lanai framed by tropical palms and water views. Upstairs, the layout is designed for comfort and convenience. The primary suite serves as a serene retreat with water views, large closet space, and barn-door entry into an upgraded bathroom featuring dual vanities, white shiplap walls, and a walk-in shower with floor-to-ceiling marble tile and gold hardware accents. Just down the hall, the secondary bedroom, which also catches a peekaboo Gullf view, is accompanied by a second full bathroom and ther is also a dedicated upstairs laundry closet with front-loading washer and dryer units. Outside, the property enjoys tranquil views of lush tropical foliage and a quiet island setting, complete with recent structural and mechanical improvements like updated windows, a brand new roof, 2021 air conditioning units, and a private garage with a recently installed hurricane-rated garage door. Cedars Tennis Club provides an unmatched resort-style atmosphere. Meander along lit boardwalks winding through mangroves to access an exceptional array of community amenities, including a heated Junior Olympic-sized swimming pool, a vibrant tiki bar, nine Har-Tru tennis courts, three Har-Tru pickleball courts, a clubhouse with a pro shop, a 24-hour fitness center, an on-site Google 5-star restaurant Hugo's II, a fishing pier, and a kayak launch (please note that some amenities require an additional club membership). This property has been a second home for current long time owners, but similair neighboring properties boasts a proven track record as a lucrative short-term rental, consistently producing roughly $50,000 in net annual revenue after platform fees. Furthermore, it offers a rare level of operational flexibility for Longboat Key, permitting up to 26 rental cycles per year. When you are ready to venture out, you are within easy walking distance of Longboat Key's world-renowned sugary white sand beaches, the tranquil trails of Joan Durante Park, and local culinary staples like Harry's Deli & Continental Kitchen, Lo-Key Bar and Grill and Euphemia Haye Restaurant & The Haye Loft. For broader entertainment, shopping, and cultural experiences, St. Armands Circle, downtown Sarasota, the Ringling Museum complex, Mote Marine and Anna Maria Island are just a short drive away. Whether you are searching for the dream beach house, a lucrative investment property, or your own private full-time retreat complete with stunning evening sunsets, this Longboat Key gem delivers on every front

2 Beds ⋅ 3 Baths ⋅ Cedars East SubDv. ⋅ 34228 Zip Code

Discover your ultimate island escape in this beautifully updated, fully furnished, and pet-friendly 2-bedroom, 2.5-bathroom townhome located within the desirable Cedars Tennis Resort & Club on Longboat Key. Set across a lush, village-like community enveloped by nature on the island's scenic north end, this property offers a rare combination of relaxed coastal living and an excellent short-term rental opportunity featuring a flexible two-week policy. Step inside to find a turnkey, coastal-chic interior highlighted by crisp shiplap accents, warm wood-style flooring, and elegant metallic hardware throughout. The updated kitchen features white shaker cabinetry, premium stone countertops, custom tile backsplash, and a breakfast bar with seating, all while offering a subtle peekaboo views of the glistening Gulf of Mexico. It flows seamlessly into a bright dining space framed by a shell-pendant chandelier and an inviting living room that opens through sliding glass doors to a private, screened lanai framed by tropical palms and water views. Upstairs, the layout is designed for comfort and convenience. The primary suite serves as a serene retreat with water views, large closet space, and barn-door entry into an upgraded bathroom featuring dual vanities, white shiplap walls, and a walk-in shower with floor-to-ceiling marble tile and gold hardware accents. Just down the hall, the secondary bedroom, which also catches a peekaboo Gullf view, is accompanied by a second full bathroom and ther is also a dedicated upstairs laundry closet with front-loading washer and dryer units. Outside, the property enjoys tranquil views of lush tropical foliage and a quiet island setting, complete with recent structural and mechanical improvements like updated windows, a brand new roof, 2021 air conditioning units, and a private garage with a recently installed hurricane-rated garage door. Cedars Tennis Club provides an unmatched resort-style atmosphere. Meander along lit boardwalks winding through mangroves to access an exceptional array of community amenities, including a heated Junior Olympic-sized swimming pool, a vibrant tiki bar, nine Har-Tru tennis courts, three Har-Tru pickleball courts, a clubhouse with a pro shop, a 24-hour fitness center, an on-site Google 5-star restaurant Hugo's II, a fishing pier, and a kayak launch (please note that some amenities require an additional club membership). This property has been a second home for current long time owners, but similair neighboring properties boasts a proven track record as a lucrative short-term rental, consistently producing roughly $50,000 in net annual revenue after platform fees. Furthermore, it offers a rare level of operational flexibility for Longboat Key, permitting up to 26 rental cycles per year. When you are ready to venture out, you are within easy walking distance of Longboat Key's world-renowned sugary white sand beaches, the tranquil trails of Joan Durante Park, and local culinary staples like Harry's Deli & Continental Kitchen, Lo-Key Bar and Grill and Euphemia Haye Restaurant & The Haye Loft. For broader entertainment, shopping, and cultural experiences, St. Armands Circle, downtown Sarasota, the Ringling Museum complex, Mote Marine and Anna Maria Island are just a short drive away. Whether you are searching for the dream beach house, a lucrative investment property, or your own private full-time retreat complete with stunning evening sunsets, this Longboat Key gem delivers on every front

521 Forest Way, Longboat Key

5461 Gulf Of Mexico Drive Unit 304, Longboat Key

$1,495,000

Virtually Staged. Step directly onto the sand from this pristine beachfront condo, where panoramic views of the ocean set the scene for total relaxation. Designed with an open-concept layout, the living area features 24x48 Carrara-style matte porcelain floor tile, wall-to-wall glass sliding doors that frame uninterrupted water views and open to a private covered balcony with a powered retractable screen as well as a security screen on both the balcony and master bedroom windows and all new impact windows and sliders. The Chefs kitchen features endless counter space and quartzite counter tops with full height quartzite backsplash, a breakfast bar, soft close cabinets and drawers, multiple custom drawers insert with organizers, dividers and pull outs. The luxury stainless-steel appliances include Sub Zero paneled triple-column integrated refrigeration suite with a 36” refrigerator, 18” freezer and 24” wine tower, a Marvel undercounter refrigerated beverage center, Café induction cooktop/double convection range and Café glass range hood. The ocean facing main bedroom with balcony access, offers a custom geometric coffered ceiling design with inset lighting, custom-built walk-in closet, Hunter Douglas dual electric shades with light filtering and black out shades. The elegant primary bath features custom cabinetry with under-cabinet lighting and generous storage including linen tower, pull out laundry hamper, built-in makeup area, dual vanities, marble counter tops, custom Glass enclosure and two shower heads with polished nickel individual Hansgrohe thermostatic valves. The large guest bedroom with wall-to-wall windows has a custom closet with mirrored pocket closet door as well as Hunter Douglas dual electric shades with light filtering and black out shades. The Guest bathroom has marble countertops, mosaic marble floor, European style floating vanity with under-cabinet lighting, double shower heads with Hansgrohe thermostatic valve and a custom glass enclosure. The laundry closet has a full-sized LG front loading washer and dryer with laundry folding quartzite countertop over the washer and dryer and upper cabinetry for storage. This residence comes with an enclosed under building parking space and a large storage closet with shelving. Amenities include a heated swimming pool surrounded by lush landscaping, tennis and pickleball court, beautiful dune walkway over to the beach, a grilling area, private beach access and an on-site property manager. This is a well-maintained boutique community of 2 buildings with only 26 total residences, pet friendly and walkable to 5 restaurants. Being offered partially furnished.

2 Beds ⋅ 2 Baths ⋅ Longboat Cove SubDv. ⋅ 34228 Zip Code

Virtually Staged. Step directly onto the sand from this pristine beachfront condo, where panoramic views of the ocean set the scene for total relaxation. Designed with an open-concept layout, the living area features 24x48 Carrara-style matte porcelain floor tile, wall-to-wall glass sliding doors that frame uninterrupted water views and open to a private covered balcony with a powered retractable screen as well as a security screen on both the balcony and master bedroom windows and all new impact windows and sliders. The Chefs kitchen features endless counter space and quartzite counter tops with full height quartzite backsplash, a breakfast bar, soft close cabinets and drawers, multiple custom drawers insert with organizers, dividers and pull outs. The luxury stainless-steel appliances include Sub Zero paneled triple-column integrated refrigeration suite with a 36” refrigerator, 18” freezer and 24” wine tower, a Marvel undercounter refrigerated beverage center, Café induction cooktop/double convection range and Café glass range hood. The ocean facing main bedroom with balcony access, offers a custom geometric coffered ceiling design with inset lighting, custom-built walk-in closet, Hunter Douglas dual electric shades with light filtering and black out shades. The elegant primary bath features custom cabinetry with under-cabinet lighting and generous storage including linen tower, pull out laundry hamper, built-in makeup area, dual vanities, marble counter tops, custom Glass enclosure and two shower heads with polished nickel individual Hansgrohe thermostatic valves. The large guest bedroom with wall-to-wall windows has a custom closet with mirrored pocket closet door as well as Hunter Douglas dual electric shades with light filtering and black out shades. The Guest bathroom has marble countertops, mosaic marble floor, European style floating vanity with under-cabinet lighting, double shower heads with Hansgrohe thermostatic valve and a custom glass enclosure. The laundry closet has a full-sized LG front loading washer and dryer with laundry folding quartzite countertop over the washer and dryer and upper cabinetry for storage. This residence comes with an enclosed under building parking space and a large storage closet with shelving. Amenities include a heated swimming pool surrounded by lush landscaping, tennis and pickleball court, beautiful dune walkway over to the beach, a grilling area, private beach access and an on-site property manager. This is a well-maintained boutique community of 2 buildings with only 26 total residences, pet friendly and walkable to 5 restaurants. Being offered partially furnished.

5461 Gulf Of Mexico Drive Unit 304, Longboat Key

3453 Gulf Of Mexico Drive Unit 242, Longboat Key

$489,900

Sea Horse is a resort community on the Gulf of Longboat Key and this unit offers a large balcony with sweeping views of the Gulf, beach, pool and epic Longboat Key sunsets. Unit 242 is a deluxe 1 bedroom with an open kitchen, dining room and living for guests to gather and a private bedroom with ensuite. The living room and bedroom share the balcony. As a resort, the on-site management office handles your rentals, maintenance, and guest needs. Parking is limited to one car for this unit. This is a quality investment property and rental projections are available upon request, but also consider this your little oasis to visit, enjoy and when you leave it's taken care of.

1 Beds ⋅ 1 Baths ⋅ Sea Horse Beach Resort SubDv. ⋅ 34228 Zip Code

Sea Horse is a resort community on the Gulf of Longboat Key and this unit offers a large balcony with sweeping views of the Gulf, beach, pool and epic Longboat Key sunsets. Unit 242 is a deluxe 1 bedroom with an open kitchen, dining room and living for guests to gather and a private bedroom with ensuite. The living room and bedroom share the balcony. As a resort, the on-site management office handles your rentals, maintenance, and guest needs. Parking is limited to one car for this unit. This is a quality investment property and rental projections are available upon request, but also consider this your little oasis to visit, enjoy and when you leave it's taken care of.

3453 Gulf Of Mexico Drive Unit 242, Longboat Key

5055 Gulf Of Mexico Drive Unit 115, Longboat Key

$750,000

Welcome to effortless Gulf-front living at Club Longboat Beach & Tennis Resort, one of Longboat Key’s sought-after beachfront communities. This beautifully updated three-bedroom, two-bath residence is offered turnkey furnished, making it an exceptional opportunity for a full-time residence, coastal retreat or potential income-producing investment. In desirable Building 1, this spacious first-floor residence offers approximately 1,484 square feet of comfortable, thoughtfully designed living space with the rare convenience of no elevators or long walks. The open, split-bedroom floor plan features wide-plank flooring, a light and inviting coastal palette, and an easy flow for everyday living and entertaining. The updated kitchen features crisp white cabinetry, stainless steel appliances, under-cabinet lighting, a glass tile backsplash and a large center island with seating. Floor-to-ceiling sliders in the great room open to a private, lushly landscaped patio, extending the living space outdoors and creating a peaceful place to enjoy the Longboat Key lifestyle. The spacious primary suite offers direct patio access, a beautifully updated bath with walk-in glass shower and generous closet space. Two additional bedrooms provide flexibility for family and guests, including a den/third bedroom with Murphy bed. The current owner recently updated a second full bath and the laundry room, which has full-size washer and dryer and additional laundry cabinetry. The unit's abundant storage throughout completes the interior. Just outside your front door is a private storage room and covered parking space, with ample additional guest and resident parking throughout the community. Club Longboat offers approximately 750 feet of direct Gulf-front beach and an exceptional resort-style lifestyle. Amenities include eight Har-Tru tennis courts, several lighted for evening play, an on-site tennis professional, pickleball, two heated swimming pools including separate adult and family pool areas, spa/whirlpool, sauna, beach chairs and umbrellas, grilling areas, bocce, fishing, on-site management and an active social calendar. An updated clubhouse with fitness and social spaces is also planned as part of the community’s exciting improvements ahead. Owners enjoy a welcoming community with regular social events, including Friday happy hours and seasonal celebrations. Club Longboat is also pet-friendly for owners and offers exceptional rental flexibility, with a 30-day minimum and up to 12 leases per year. For buyers looking to offset ownership costs, this residence offers a proven rental history. There are currently future bookings of $59k for 3rd Qu 2026 through April 2027. Full details and rental history available upon request. The combination of a three-bedroom floor plan, turnkey furnishings, direct Gulf access and flexible leasing has made this an exceptionally desirable rental. Ideally on the Gulf side of Longboat Key, you are minutes from outstanding dining, boating, golf and recreation, with the shops and restaurants of St. Armands Circle and the arts and culture of downtown Sarasota just a short drive away. Whether you are searching for a turnkey beach home, seasonal escape or investment property, this beautifully furnished Club Longboat residence offers the combination buyers want most, direct gulf access, resort-style amenities, three bedrooms, rental flexibility and unmistakable lifestyle of Longboat Key. Simply arrive, unpack and head to the beach.

3 Beds ⋅ 2 Baths ⋅ Club Longboat Beach & Tennis SubDv. ⋅ 34228 Zip Code

Welcome to effortless Gulf-front living at Club Longboat Beach & Tennis Resort, one of Longboat Key’s sought-after beachfront communities. This beautifully updated three-bedroom, two-bath residence is offered turnkey furnished, making it an exceptional opportunity for a full-time residence, coastal retreat or potential income-producing investment. In desirable Building 1, this spacious first-floor residence offers approximately 1,484 square feet of comfortable, thoughtfully designed living space with the rare convenience of no elevators or long walks. The open, split-bedroom floor plan features wide-plank flooring, a light and inviting coastal palette, and an easy flow for everyday living and entertaining. The updated kitchen features crisp white cabinetry, stainless steel appliances, under-cabinet lighting, a glass tile backsplash and a large center island with seating. Floor-to-ceiling sliders in the great room open to a private, lushly landscaped patio, extending the living space outdoors and creating a peaceful place to enjoy the Longboat Key lifestyle. The spacious primary suite offers direct patio access, a beautifully updated bath with walk-in glass shower and generous closet space. Two additional bedrooms provide flexibility for family and guests, including a den/third bedroom with Murphy bed. The current owner recently updated a second full bath and the laundry room, which has full-size washer and dryer and additional laundry cabinetry. The unit's abundant storage throughout completes the interior. Just outside your front door is a private storage room and covered parking space, with ample additional guest and resident parking throughout the community. Club Longboat offers approximately 750 feet of direct Gulf-front beach and an exceptional resort-style lifestyle. Amenities include eight Har-Tru tennis courts, several lighted for evening play, an on-site tennis professional, pickleball, two heated swimming pools including separate adult and family pool areas, spa/whirlpool, sauna, beach chairs and umbrellas, grilling areas, bocce, fishing, on-site management and an active social calendar. An updated clubhouse with fitness and social spaces is also planned as part of the community’s exciting improvements ahead. Owners enjoy a welcoming community with regular social events, including Friday happy hours and seasonal celebrations. Club Longboat is also pet-friendly for owners and offers exceptional rental flexibility, with a 30-day minimum and up to 12 leases per year. For buyers looking to offset ownership costs, this residence offers a proven rental history. There are currently future bookings of $59k for 3rd Qu 2026 through April 2027. Full details and rental history available upon request. The combination of a three-bedroom floor plan, turnkey furnishings, direct Gulf access and flexible leasing has made this an exceptionally desirable rental. Ideally on the Gulf side of Longboat Key, you are minutes from outstanding dining, boating, golf and recreation, with the shops and restaurants of St. Armands Circle and the arts and culture of downtown Sarasota just a short drive away. Whether you are searching for a turnkey beach home, seasonal escape or investment property, this beautifully furnished Club Longboat residence offers the combination buyers want most, direct gulf access, resort-style amenities, three bedrooms, rental flexibility and unmistakable lifestyle of Longboat Key. Simply arrive, unpack and head to the beach.

5055 Gulf Of Mexico Drive Unit 115, Longboat Key

$2,398,000

Ideally situated at the north end of Longboat Key within the confines of The Preserve of Longbeach rests this stunning modern coastal residence. The tastemaker’s tastemaker who owns this masterpiece has imbued it with a seamless design incorporating an open floorplan where the great room, dining area and kitchen reflect a rare integration of all living space. An immediately accessible covered loggia terrace further expands these spaces, but also belies an astounding outdoor arena that houses a pool, lush landscaping and yet another covered sitting area. The first floor primary suite spaciously allows for King size bedding, a sitting area, access to the aforementioned terrace, and a striking en suite w/soaking tub. A forth bedroom or Den is adjacent to a half bath and full sized utility room. Both upstairs bedrooms come w/en suites and capacious closets. 3 of the 4 bedrooms have direct balcony and/or terrace access. The great room features a fireplace which serves as a focal point of earthiness and ease. Bathed in timeless paint treatments, heirloom modern lighting and fixtures the appointments lend for a spectacular dwelling. Exquisite flooring, custom cabinetry, stone counters and Viking appliances resonate a profoundly less but more aesthetic. A 3 car garage allows for easy maneuverability. A whole house elevator maximizes usage for all. Ideal as a family home, secondary Gulf Coastal residence, part-time rental or whatever your family’s dynamic demands. This very particular stretch of sand, surf and sky offers accessibility to a myriad of dining venues, as charming & kitschy as you’d like, or more refined, boat ramp access and recreational opportunities at your leisure. We await your visit, and anticipate your future legacy within the heart that is this home..

4 Beds ⋅ 4 Baths ⋅ Long Beach SubDv. ⋅ 34228 Zip Code

Ideally situated at the north end of Longboat Key within the confines of The Preserve of Longbeach rests this stunning modern coastal residence. The tastemaker’s tastemaker who owns this masterpiece has imbued it with a seamless design incorporating an open floorplan where the great room, dining area and kitchen reflect a rare integration of all living space. An immediately accessible covered loggia terrace further expands these spaces, but also belies an astounding outdoor arena that houses a pool, lush landscaping and yet another covered sitting area. The first floor primary suite spaciously allows for King size bedding, a sitting area, access to the aforementioned terrace, and a striking en suite w/soaking tub. A forth bedroom or Den is adjacent to a half bath and full sized utility room. Both upstairs bedrooms come w/en suites and capacious closets. 3 of the 4 bedrooms have direct balcony and/or terrace access. The great room features a fireplace which serves as a focal point of earthiness and ease. Bathed in timeless paint treatments, heirloom modern lighting and fixtures the appointments lend for a spectacular dwelling. Exquisite flooring, custom cabinetry, stone counters and Viking appliances resonate a profoundly less but more aesthetic. A 3 car garage allows for easy maneuverability. A whole house elevator maximizes usage for all. Ideal as a family home, secondary Gulf Coastal residence, part-time rental or whatever your family’s dynamic demands. This very particular stretch of sand, surf and sky offers accessibility to a myriad of dining venues, as charming & kitschy as you’d like, or more refined, boat ramp access and recreational opportunities at your leisure. We await your visit, and anticipate your future legacy within the heart that is this home..

6840 Longboat Drive S, Longboat Key

4370 Chatham Drive Unit 304, Longboat Key

$425,000

MAJOR $74,000 PRICE REDUCTION, don't miss this newly priced opportunity. Experience the best of Bay-to-Gulf living in this beautifully furnished condominium located on the top-floor in Building G at Longboat Harbour. Featuring 2 bedrooms and 2 bathrooms, this move-in-ready residence offers peaceful canal views, thoughtful updates, and exclusive access to a private, gated beach club on the Longboat Key Gulf Beach, just steps away. Building G also offers a special community feature: a dedicated bump-out area designed for residents’ outdoor gatherings and entertaining. This exclusive feature is available to only two buildings within Longboat Harbour, and Building G is one of them. The bright and inviting interior features a carpet-free design with luxury vinyl plank flooring throughout with tiled bathrooms. New lighting fixtures, custom window treatments and ceiling fans add a fresh, updated touch, while the kitchen is appointed with granite countertops and a stylish backsplash. The updated primary bathroom provides additional comfort and modern appeal with custom vanity and cabinet storage. A new HVAC system installed in 2025 offers added peace of mind. Step outside to the spacious screened lanai, where beautiful canal views create a relaxing backdrop for everyday living, and on those lucky days, you may even catch a glimpse of manatees swimming peacefully through the water. Enhanced by a ceiling fan, this private outdoor space is perfect for enjoying morning coffee, reading a good book, entertaining guests, or unwinding at the end of the day. The condominium is being sold furnished with carefully selected pieces that complement the home’s coastal style and create a warm, comfortable atmosphere. Whether you are searching for a full-time residence, seasonal getaway, or coastal vacation retreat, this property is ready to enjoy from the moment you arrive. Longboat Harbour at Longboat Key offers an exceptional waterfront lifestyle with access to both Sarasota Bay and the beautiful Longboat Key Beach. The community’s private, gated beach club provides a convenient place to relax on the sand, enjoy the Gulf breeze, and take in beautiful Florida sunsets. Residents also enjoy an impressive selection of resort-style amenities, including four heated swimming pools, a fully equipped fitness center, tennis and pickleball courts, fishing piers, kayak & bicycle storage, and boat slips available on a first-come, first-served basis. The community clubhouse/banquet hall offers social events and activities, providing plenty of opportunities to meet neighbors and enjoy an active coastal lifestyle. Ideally situated on Longboat Key, this gated waterfront community offers convenient access to some of the area’s best dining, shopping, and entertainment while maintaining a peaceful and private setting. Whether used as a serene retreat, vacation property, or full-time residence, this furnished condominium provides everything needed to experience the very best of Longboat Key’s Bay-to-Gulf lifestyle. Schedule your private showing or request your virtual tour today, don't miss out this GEM on Longboat Key.

2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code

MAJOR $74,000 PRICE REDUCTION, don't miss this newly priced opportunity. Experience the best of Bay-to-Gulf living in this beautifully furnished condominium located on the top-floor in Building G at Longboat Harbour. Featuring 2 bedrooms and 2 bathrooms, this move-in-ready residence offers peaceful canal views, thoughtful updates, and exclusive access to a private, gated beach club on the Longboat Key Gulf Beach, just steps away. Building G also offers a special community feature: a dedicated bump-out area designed for residents’ outdoor gatherings and entertaining. This exclusive feature is available to only two buildings within Longboat Harbour, and Building G is one of them. The bright and inviting interior features a carpet-free design with luxury vinyl plank flooring throughout with tiled bathrooms. New lighting fixtures, custom window treatments and ceiling fans add a fresh, updated touch, while the kitchen is appointed with granite countertops and a stylish backsplash. The updated primary bathroom provides additional comfort and modern appeal with custom vanity and cabinet storage. A new HVAC system installed in 2025 offers added peace of mind. Step outside to the spacious screened lanai, where beautiful canal views create a relaxing backdrop for everyday living, and on those lucky days, you may even catch a glimpse of manatees swimming peacefully through the water. Enhanced by a ceiling fan, this private outdoor space is perfect for enjoying morning coffee, reading a good book, entertaining guests, or unwinding at the end of the day. The condominium is being sold furnished with carefully selected pieces that complement the home’s coastal style and create a warm, comfortable atmosphere. Whether you are searching for a full-time residence, seasonal getaway, or coastal vacation retreat, this property is ready to enjoy from the moment you arrive. Longboat Harbour at Longboat Key offers an exceptional waterfront lifestyle with access to both Sarasota Bay and the beautiful Longboat Key Beach. The community’s private, gated beach club provides a convenient place to relax on the sand, enjoy the Gulf breeze, and take in beautiful Florida sunsets. Residents also enjoy an impressive selection of resort-style amenities, including four heated swimming pools, a fully equipped fitness center, tennis and pickleball courts, fishing piers, kayak & bicycle storage, and boat slips available on a first-come, first-served basis. The community clubhouse/banquet hall offers social events and activities, providing plenty of opportunities to meet neighbors and enjoy an active coastal lifestyle. Ideally situated on Longboat Key, this gated waterfront community offers convenient access to some of the area’s best dining, shopping, and entertainment while maintaining a peaceful and private setting. Whether used as a serene retreat, vacation property, or full-time residence, this furnished condominium provides everything needed to experience the very best of Longboat Key’s Bay-to-Gulf lifestyle. Schedule your private showing or request your virtual tour today, don't miss out this GEM on Longboat Key.

4370 Chatham Drive Unit 304, Longboat Key

$3,999,990

Exceptional waterfront living meets serious Longboat Key boating in this beautifully updated 4300 sf residence in Country Club Shores. Expansive water views, flexible living spaces and deeded beach access create a home designed for the Florida lifestyle. From the moment you enter, the water takes center stage and you know you're home. Generous living and dining spaces give the interior a sophisticated yet relaxed coastal feel. Inside, enjoy the high ceilings, Italian tile floors and a fireplace - and be transported through the wall of windows to blue waters of your pool and dock. The beautifully appointed kitchen is designed for both entertaining and everyday living with Sub-Zero French-door refrigeration and Wolf double ovens and cooktop, Asko dishwasher, new quartz countertops and a floating island with seating. Separate dining areas provide plenty of room for everything from casual mornings to entertaining a crowd. The primary suite offers a private retreat with a balcony and long-range water views - complete with a spacious bath featuring dual sinks and a walk-in shower. Additional oversized suites both upstairs and downstairs offer flexibility for a study or gym. Even more unique is the home's ability to accommodate extended family and guests. A separate entrance opens to its own living area and full bath, while upstairs are two additional bedrooms, a full bath and private sauna—creating a wonderfully versatile space for guests, multigenerational living or extended stays. Outside is where this property truly distinguishes itself. A generous pavered waterfront deck surrounds the Pebble-finish pool and spa, creating multiple areas for lounging, dining and entertaining. The fenced backyard leads to an impressive boating setup with two boat lifts—approximately 24,000 lbs. and 20,000 lbs.— newer seawall and composite dock plus a fish-cleaning station - making it exceptionally well equipped for the boating enthusiast. You're only four homes from the open waters of Sarasota Bay - providing immediate water access and minutes to the open Gulf. And if beach is more your style - enjoy the neighborhood's deeded access to the Gulf of Mexico- right across the street! Significant improvements add another level of value and peace of mind - including a newer roof (2020), all impact windows and doors, updated seawall and dock infrastructure (including plumbing and electrical service to the dock), extensive paver patio, pool resurfacing, interior and exterior painting, tankless hot water heater, landscaping and gas service ready to go for the next owner. And there's room for the toys with a two-car garage with workshop area and storage. You're only five minutes to vibrant St. Armand's Circle for shopping and dining - and a short drive to downtown Sarasota's cultural and entertainment venues. A special home to enjoy everything that makes Longboat Key living so special.

5 Beds ⋅ 5 Baths ⋅ Country Club Shores SubDv. ⋅ 34228 Zip Code

Exceptional waterfront living meets serious Longboat Key boating in this beautifully updated 4300 sf residence in Country Club Shores. Expansive water views, flexible living spaces and deeded beach access create a home designed for the Florida lifestyle. From the moment you enter, the water takes center stage and you know you're home. Generous living and dining spaces give the interior a sophisticated yet relaxed coastal feel. Inside, enjoy the high ceilings, Italian tile floors and a fireplace - and be transported through the wall of windows to blue waters of your pool and dock. The beautifully appointed kitchen is designed for both entertaining and everyday living with Sub-Zero French-door refrigeration and Wolf double ovens and cooktop, Asko dishwasher, new quartz countertops and a floating island with seating. Separate dining areas provide plenty of room for everything from casual mornings to entertaining a crowd. The primary suite offers a private retreat with a balcony and long-range water views - complete with a spacious bath featuring dual sinks and a walk-in shower. Additional oversized suites both upstairs and downstairs offer flexibility for a study or gym. Even more unique is the home's ability to accommodate extended family and guests. A separate entrance opens to its own living area and full bath, while upstairs are two additional bedrooms, a full bath and private sauna—creating a wonderfully versatile space for guests, multigenerational living or extended stays. Outside is where this property truly distinguishes itself. A generous pavered waterfront deck surrounds the Pebble-finish pool and spa, creating multiple areas for lounging, dining and entertaining. The fenced backyard leads to an impressive boating setup with two boat lifts—approximately 24,000 lbs. and 20,000 lbs.— newer seawall and composite dock plus a fish-cleaning station - making it exceptionally well equipped for the boating enthusiast. You're only four homes from the open waters of Sarasota Bay - providing immediate water access and minutes to the open Gulf. And if beach is more your style - enjoy the neighborhood's deeded access to the Gulf of Mexico- right across the street! Significant improvements add another level of value and peace of mind - including a newer roof (2020), all impact windows and doors, updated seawall and dock infrastructure (including plumbing and electrical service to the dock), extensive paver patio, pool resurfacing, interior and exterior painting, tankless hot water heater, landscaping and gas service ready to go for the next owner. And there's room for the toys with a two-car garage with workshop area and storage. You're only five minutes to vibrant St. Armand's Circle for shopping and dining - and a short drive to downtown Sarasota's cultural and entertainment venues. A special home to enjoy everything that makes Longboat Key living so special.

560 Chipping Lane, Longboat Key

729 Saint Judes Drive S Unit 2, Longboat Key

$525,000

Beautifully renovated waterfront unit at 729 St. Jude’s Way with gorgeous water views and a boat dock, plus easy access to the Intracoastal Waterway. Renovated from top to bottom, this move-in-ready home features all-new flooring, a beautifully updated kitchen and bathroom, and brand-new appliances. Ideally located near a variety of restaurants, beautiful beaches, downtown Sarasota, and Anna Maria Island. Enjoy the perfect blend of waterfront living, modern updates, and convenient access to everything the area has to offer!

2 Beds ⋅ 2 Baths ⋅ St Judes Apts SubDv. ⋅ 34228 Zip Code

Beautifully renovated waterfront unit at 729 St. Jude’s Way with gorgeous water views and a boat dock, plus easy access to the Intracoastal Waterway. Renovated from top to bottom, this move-in-ready home features all-new flooring, a beautifully updated kitchen and bathroom, and brand-new appliances. Ideally located near a variety of restaurants, beautiful beaches, downtown Sarasota, and Anna Maria Island. Enjoy the perfect blend of waterfront living, modern updates, and convenient access to everything the area has to offer!

729 Saint Judes Drive S Unit 2, Longboat Key

3802 Gulf Of Mexico Drive Unit A203, Longboat Key

$399,000

Gulf views! Just bring your flip flops and bathing suit to this move-in ready 2br/2ba condo on the 2nd floor in Beach Harbor Club. This beautifully maintained Gulf-to-bay community offers boat slips on the bay and private beach access on the Gulf side, as well as pool, clubhouse, gym and private beach access just across the street! This unit has been tastefully updated to include an all-new bright open kitchen with custom cabinetry, stone counters and high-end appliances, including a Fisher & Paykel fridge, a two-drawer Cafe dishwasher, and a Cafe two-oven, six-burner stove. Flooring throughout was replaced with a light blond luxury vinyl plank. Both baths had updates including cabinetry and same quartz countertops found in the kitchen. The AC was replaced in 2024. This home also has a sweet view of the Gulf from the outdoor seating area in the front. The monthly fee includes water, trash, internet, cable, and pest control, as well as the usual insurances, and exterior maintenances. Beach Harbor Club is an active and amenities-rich community with boat docks, a pool, a gym, private beach access, kayak storage, a ground-level storage closet for beach gear, a beautiful clubhouse and just upstairs from this unit is a wonderful rooftop deck for sunset viewing. No effort required to start living your beach life dream today!

2 Beds ⋅ 2 Baths ⋅ Beach Harbor Club SubDv. ⋅ 34228 Zip Code

Gulf views! Just bring your flip flops and bathing suit to this move-in ready 2br/2ba condo on the 2nd floor in Beach Harbor Club. This beautifully maintained Gulf-to-bay community offers boat slips on the bay and private beach access on the Gulf side, as well as pool, clubhouse, gym and private beach access just across the street! This unit has been tastefully updated to include an all-new bright open kitchen with custom cabinetry, stone counters and high-end appliances, including a Fisher & Paykel fridge, a two-drawer Cafe dishwasher, and a Cafe two-oven, six-burner stove. Flooring throughout was replaced with a light blond luxury vinyl plank. Both baths had updates including cabinetry and same quartz countertops found in the kitchen. The AC was replaced in 2024. This home also has a sweet view of the Gulf from the outdoor seating area in the front. The monthly fee includes water, trash, internet, cable, and pest control, as well as the usual insurances, and exterior maintenances. Beach Harbor Club is an active and amenities-rich community with boat docks, a pool, a gym, private beach access, kayak storage, a ground-level storage closet for beach gear, a beautiful clubhouse and just upstairs from this unit is a wonderful rooftop deck for sunset viewing. No effort required to start living your beach life dream today!

3802 Gulf Of Mexico Drive Unit A203, Longboat Key