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An Extraordinary Gulf-Front Homesite on North Longboat Key. Imagine dolphins dancing in the turquoise waters as the sun sets in a magnificent display of color. Sit with your feet in the cool sand and toast another perfect day. Welcome to an exceptional opportunity to create your dream beachfront estate on exclusive Longboat Key. Spanning a full acre with 100 feet of Gulf frontage, this remarkable homesite offers a rare canvas for a custom coastal residence in one of Sarasota’s most coveted locations. With your own private beach of powder-soft sands, the property invites you to design a sanctuary where breathtaking sunsets, endless Gulf views, and the soothing rhythm of the waves become part of everyday life. Envision a stunning architectural masterpiece with expansive terraces, a resort-style pool, lush landscaping, and elegant indoor-outdoor living spaces designed to embrace the spectacular coastline. You can build your vision from the ground up. Located near the north end of Longboat Key, this one-acre setting blends natural tropical beauty with easy access to the island’s best experiences. Waterfront dining and championship golf and tennis are just a short drive away. Explore Joan M. Durante Park for scenic boating, kayaking, and strolling along pristine Sarasota Bay. Anna Maria Island offers charming island character, while St. Armands Circle and downtown Sarasota provide upscale shopping, acclaimed restaurants, and an outstanding cultural scene. Longboat Key is celebrated for its tranquil atmosphere and unparalleled coastal surroundings. Here, mornings begin with peaceful beach walks and afternoons unfold beneath the Florida sun. As evening descends, nature takes center stage as the lingering hues of the setting sun give way to a brilliant, star-studded sky, transforming the heavens into a dazzling tapestry of wonder and serenity. A rare opportunity to build a one-of-a-kind estate in an exquisite beachfront setting, tailored to your personality, style, and specifications. Your dream home. Your own stretch of paradise. The timeless splendor of the Gulf.

6 Beds ⋅ 6 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code

An Extraordinary Gulf-Front Homesite on North Longboat Key. Imagine dolphins dancing in the turquoise waters as the sun sets in a magnificent display of color. Sit with your feet in the cool sand and toast another perfect day. Welcome to an exceptional opportunity to create your dream beachfront estate on exclusive Longboat Key. Spanning a full acre with 100 feet of Gulf frontage, this remarkable homesite offers a rare canvas for a custom coastal residence in one of Sarasota’s most coveted locations. With your own private beach of powder-soft sands, the property invites you to design a sanctuary where breathtaking sunsets, endless Gulf views, and the soothing rhythm of the waves become part of everyday life. Envision a stunning architectural masterpiece with expansive terraces, a resort-style pool, lush landscaping, and elegant indoor-outdoor living spaces designed to embrace the spectacular coastline. You can build your vision from the ground up. Located near the north end of Longboat Key, this one-acre setting blends natural tropical beauty with easy access to the island’s best experiences. Waterfront dining and championship golf and tennis are just a short drive away. Explore Joan M. Durante Park for scenic boating, kayaking, and strolling along pristine Sarasota Bay. Anna Maria Island offers charming island character, while St. Armands Circle and downtown Sarasota provide upscale shopping, acclaimed restaurants, and an outstanding cultural scene. Longboat Key is celebrated for its tranquil atmosphere and unparalleled coastal surroundings. Here, mornings begin with peaceful beach walks and afternoons unfold beneath the Florida sun. As evening descends, nature takes center stage as the lingering hues of the setting sun give way to a brilliant, star-studded sky, transforming the heavens into a dazzling tapestry of wonder and serenity. A rare opportunity to build a one-of-a-kind estate in an exquisite beachfront setting, tailored to your personality, style, and specifications. Your dream home. Your own stretch of paradise. The timeless splendor of the Gulf.

Longboat Key

$423,750

Spanish Main Yacht Club is a 55+ community. There are 213 villa, ground-level attached condo units in this condo complex. It has a marina with boat docks, a clubhouse, swimming pool, shuffleboard courts, and private beach access. Signs are not permitted and the streets are private and maintained by the Association. Roof maintenance and replacement are the responsibility of individual unit owners. All marina and boating inquiries should be directed to the Dock Master, Ross Wenum. Docks and slips are allowed on a first come first serve basis with sizes from 14 feet to 40 feet. It has its own marina with direct access to Sarasota Bay. The boat must be fully owned by the unit owner, and the unit owner must be in residence 155 days of the calendar year. There is a $750 non-refundable application fee for a dock or boat slip. Small boats are $200 a year, medium boats are $250 a year and large boats are $300 a year. The monthly condo fee covers the insurance for the community common elements and exterior of the buildings, all property management, water, sewer, trash collection, lawn mowing, palm tree trimming, general maintenance of the common grounds and pool, and exterior painting. Unit owners are separately responsible for electricity, cable/internet, pest control, landscaping around their villas, and their unit property taxes. There is an area off the entrance to the right - the boneyard, named because of the historical bones found there. There is a maintenance building, a vehicle wash area, a community dumpster, overflow parking for extra vehicles, boat trailers, and RV's. This two-bedroom, two bathroom unit is 1,429 square feet of air-conditioned space with Kitchen, Living Room/Dining Room combination and an additional 225 square foot glassed-enclosed rear lanai (porch), for a total of 1,765 under roof. The current jalousie windows will be replaced with new hurricane windows in the near future and this has been paid for. Off this lanai is the inside utility room 7 x 9 with washer/dryer hook up (washer/dryer not included), and ample extra storage space. Each unit has its own carport with a 5 x 7 storage closet attached to the carport. The previous washer/dryer hookup is still there as is the new hot water heater. This unit has been totally renovated after the hurricanes of 2024 and has an all new interior inside the unit, new everything - flooring, painting, ceilings, all new stone countertops in Kitchen and both bathrooms, many new hurricane windows, new sliding glass doors and new front entry door. All new appliances, Kitchen, bathrooms, fixtures, plumbing and electricity, ceiling fans, HVAC system with the air-handler in the hallway attic and the condenser on the roof. This unit has not been lived in since the renovation has been completed. The unit is vacant, on Supra lockbox, easy to preview, show and buy. We are currently priced at $423,750 which is the lowest list price of the twelve units currently for sale.

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

Spanish Main Yacht Club is a 55+ community. There are 213 villa, ground-level attached condo units in this condo complex. It has a marina with boat docks, a clubhouse, swimming pool, shuffleboard courts, and private beach access. Signs are not permitted and the streets are private and maintained by the Association. Roof maintenance and replacement are the responsibility of individual unit owners. All marina and boating inquiries should be directed to the Dock Master, Ross Wenum. Docks and slips are allowed on a first come first serve basis with sizes from 14 feet to 40 feet. It has its own marina with direct access to Sarasota Bay. The boat must be fully owned by the unit owner, and the unit owner must be in residence 155 days of the calendar year. There is a $750 non-refundable application fee for a dock or boat slip. Small boats are $200 a year, medium boats are $250 a year and large boats are $300 a year. The monthly condo fee covers the insurance for the community common elements and exterior of the buildings, all property management, water, sewer, trash collection, lawn mowing, palm tree trimming, general maintenance of the common grounds and pool, and exterior painting. Unit owners are separately responsible for electricity, cable/internet, pest control, landscaping around their villas, and their unit property taxes. There is an area off the entrance to the right - the boneyard, named because of the historical bones found there. There is a maintenance building, a vehicle wash area, a community dumpster, overflow parking for extra vehicles, boat trailers, and RV's. This two-bedroom, two bathroom unit is 1,429 square feet of air-conditioned space with Kitchen, Living Room/Dining Room combination and an additional 225 square foot glassed-enclosed rear lanai (porch), for a total of 1,765 under roof. The current jalousie windows will be replaced with new hurricane windows in the near future and this has been paid for. Off this lanai is the inside utility room 7 x 9 with washer/dryer hook up (washer/dryer not included), and ample extra storage space. Each unit has its own carport with a 5 x 7 storage closet attached to the carport. The previous washer/dryer hookup is still there as is the new hot water heater. This unit has been totally renovated after the hurricanes of 2024 and has an all new interior inside the unit, new everything - flooring, painting, ceilings, all new stone countertops in Kitchen and both bathrooms, many new hurricane windows, new sliding glass doors and new front entry door. All new appliances, Kitchen, bathrooms, fixtures, plumbing and electricity, ceiling fans, HVAC system with the air-handler in the hallway attic and the condenser on the roof. This unit has not been lived in since the renovation has been completed. The unit is vacant, on Supra lockbox, easy to preview, show and buy. We are currently priced at $423,750 which is the lowest list price of the twelve units currently for sale.

693 Spanish Drive N Unit 24, Longboat Key

$675,000

Virtually Staged. Views! Views! Views! A must see! Experience coastal elegance and stunning water views in this beautifully renovated 2-bedroom, 2-bathroom villa located in the active Spanish Main Yacht Club waterfront community on Longboat Key. Porcelain tile flooring flows seamlessly throughout the home, highlighting a kitchen equipped with quartz countertops, stainless steel appliances, an undermount sink, custom tile herringbone backsplash, and generous cabinet space. Crown molding elevates the open living room, which leads into a large lanai framed by hurricane-grade windows and blinds that showcase views of the Bay. The primary bedroom features a walk-in closet, while both bathrooms display custom tile tastefully outfitted that completes this custom renovation. Outside, a large patio running along the back of the home offers privacy provided by natural wetlands, with Bay access just steps away to launch your kayak. Community amenities include private deeded beach access directly across the street, open water access with boat slips available for a nominal lease, a community heated swimming pool, and a clubhouse being newly refreshed. Enjoy beautifully landscaped grounds in a convenient location just minutes from St. Armands Circle and downtown Sarasota.

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

Virtually Staged. Views! Views! Views! A must see! Experience coastal elegance and stunning water views in this beautifully renovated 2-bedroom, 2-bathroom villa located in the active Spanish Main Yacht Club waterfront community on Longboat Key. Porcelain tile flooring flows seamlessly throughout the home, highlighting a kitchen equipped with quartz countertops, stainless steel appliances, an undermount sink, custom tile herringbone backsplash, and generous cabinet space. Crown molding elevates the open living room, which leads into a large lanai framed by hurricane-grade windows and blinds that showcase views of the Bay. The primary bedroom features a walk-in closet, while both bathrooms display custom tile tastefully outfitted that completes this custom renovation. Outside, a large patio running along the back of the home offers privacy provided by natural wetlands, with Bay access just steps away to launch your kayak. Community amenities include private deeded beach access directly across the street, open water access with boat slips available for a nominal lease, a community heated swimming pool, and a clubhouse being newly refreshed. Enjoy beautifully landscaped grounds in a convenient location just minutes from St. Armands Circle and downtown Sarasota.

917 Spanish Drive N, Longboat Key

5655 Gulf Of Mexico Drive Unit A107, Longboat Key

$775,000

Enjoy Gulf-front living and gorgeous water views in this move-in-ready, two-bedroom, two-bath waterfront condominium, perfectly positioned in an elevated community just steps from the beach. This home is in impeccable condition and is designed for relaxation, with a seamless blend of comfort, style, and convenience. It's being sold turnkey with lovely furnishings. The kitchen features new Samsung stainless steel appliances, plenty of counter space, and a comfortable sitting area. An open floor plan with a large living room, remote-controlled sunshades and three-panel impact sliding glass doors opens to an inviting screened lanai with a tropical ceiling fan, blurring the lines between indoor and outdoor living. There are ceiling fans in every room. The primary suite offers a large bath with a separate water closet and a huge walk-in closet. There are also impact sliders leading out to the lanai with a view of the Gulf. The guest suite is spacious with lots of closet space. The laundry is neatly tucked away and features Bosch machines. If you love the beach and enjoy stunning sunsets, Cedars West is really the perfect place to live. This location is within close proximity to our local restaurants (Lo-Key, Harry's and Hugos), convenience shopping, and all the amenities you’ll need to enjoy life here on Longboat Key. This community has tennis, a heated pool, BBQ area, bike racks, and kayak storage. Cedars East, just across the street, offers tennis membership with a world-class facility. This financially sound community offers peace of mind with a new roof and no assessments planned. With a liberal rental policy allowing up to 26 rentals/year, this property presents an exceptional investment opportunity while still offering the flexibility to enjoy your own beach getaway. There is a lockable owner's closet in the unit. You have to see this home to really appreciate how special it is.

2 Beds ⋅ 2 Baths ⋅ Cedars West Of Longboat Inc SubDv. ⋅ 34228 Zip Code

Enjoy Gulf-front living and gorgeous water views in this move-in-ready, two-bedroom, two-bath waterfront condominium, perfectly positioned in an elevated community just steps from the beach. This home is in impeccable condition and is designed for relaxation, with a seamless blend of comfort, style, and convenience. It's being sold turnkey with lovely furnishings. The kitchen features new Samsung stainless steel appliances, plenty of counter space, and a comfortable sitting area. An open floor plan with a large living room, remote-controlled sunshades and three-panel impact sliding glass doors opens to an inviting screened lanai with a tropical ceiling fan, blurring the lines between indoor and outdoor living. There are ceiling fans in every room. The primary suite offers a large bath with a separate water closet and a huge walk-in closet. There are also impact sliders leading out to the lanai with a view of the Gulf. The guest suite is spacious with lots of closet space. The laundry is neatly tucked away and features Bosch machines. If you love the beach and enjoy stunning sunsets, Cedars West is really the perfect place to live. This location is within close proximity to our local restaurants (Lo-Key, Harry's and Hugos), convenience shopping, and all the amenities you’ll need to enjoy life here on Longboat Key. This community has tennis, a heated pool, BBQ area, bike racks, and kayak storage. Cedars East, just across the street, offers tennis membership with a world-class facility. This financially sound community offers peace of mind with a new roof and no assessments planned. With a liberal rental policy allowing up to 26 rentals/year, this property presents an exceptional investment opportunity while still offering the flexibility to enjoy your own beach getaway. There is a lockable owner's closet in the unit. You have to see this home to really appreciate how special it is.

5655 Gulf Of Mexico Drive Unit A107, Longboat Key

$22,000,000

Introducing a rare legacy estate defined by architectural distinction, extraordinary waterfront, and an exceptional sense of privacy. 6610 Gulf of Mexico Drive is the pinnacle of architectural ingenuity designed by world-renowned visionary Carl Abbott, one of the most highly decorated architects in the Florida/Caribbean region. Known for naming his most valued accomplishments, Abbott designated this spectacular residence the “House of Columns”—a remarkable expression of art in architecture inspired by the land and its surrounding natural beauty. Including the adjacent lot at 6630 Gulf of Mexico Drive further enhances the offering, providing the opportunity to construct a guest house or secondary structure—an appealing option for multigenerational living, visiting guests, or staff accommodations. Set along Sarasota’s most coveted barrier island, the property represents a singular convergence of design, landscape, and place—an enduring residential landmark of remarkable presence and provenance. A long, private drive through a dense canopy of palms and native foliage leads to this nearly five-acre peninsula property with expansive bay frontage and exceptional seclusion. Endless expanses of water and sky form a breathtaking backdrop, while the ever-shifting light throughout the day casts the home and acreage in a constantly evolving palette. Designed for multilevel living, the 6,891-square-foot home features the main living structure with separate wings connected by enclosed bridges. Walls of glass dissolve the boundaries between interior and landscape, revealing lush grounds and a brilliant bay panorama that unfolds endlessly toward the horizon. A beautifully crafted pool surrounds nearly half of the home’s exterior and mirrors the tranquil movement of the water beyond. Clean architectural lines, soaring interior volumes, and a thoughtful interplay of solid and transparent forms create a cohesive relationship between the interior and exterior. Ceilings reaching up to 21 feet allow natural light to move freely throughout the home. Every space reveals a considered balance of visual drama and functional design. With every turn, another exquisite detail reveals itself—thoughtfully composed, beautifully nuanced, and presented with quiet grandeur. As daylight fades, exterior lighting transforms the grounds into a resort-like setting, creating an inviting atmosphere where every gathering becomes a memorable experience. A private dock with two lifts provides direct access to the protected shoreline of Sarasota Bay and the Intracoastal Waterway, supporting a seamless boating lifestyle. An elevator serves the home’s multiple levels, while Lutron lighting and automated shades allow the residence to respond intuitively to changing daylight. The owner’s garage provides convenient access to the interior elevator and an additional air-conditioned four-bay garage with a generous workspace brings the total capacity to six vehicles. A whole-home generator provides added continuity and peace of mind. Impeccably maintained by its original owner, the residence reflects an uncommon level of care and stewardship. Estates of this size and caliber, architectural clarity, substantial waterfront, established boating infrastructure, development flexibility, and meticulously maintained condition are exceptionally rare. This impressive property exudes a sense of timelessness and is distinguished by its design, scale, privacy, and extraordinary location.

4 Beds ⋅ 7 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code

Introducing a rare legacy estate defined by architectural distinction, extraordinary waterfront, and an exceptional sense of privacy. 6610 Gulf of Mexico Drive is the pinnacle of architectural ingenuity designed by world-renowned visionary Carl Abbott, one of the most highly decorated architects in the Florida/Caribbean region. Known for naming his most valued accomplishments, Abbott designated this spectacular residence the “House of Columns”—a remarkable expression of art in architecture inspired by the land and its surrounding natural beauty. Including the adjacent lot at 6630 Gulf of Mexico Drive further enhances the offering, providing the opportunity to construct a guest house or secondary structure—an appealing option for multigenerational living, visiting guests, or staff accommodations. Set along Sarasota’s most coveted barrier island, the property represents a singular convergence of design, landscape, and place—an enduring residential landmark of remarkable presence and provenance. A long, private drive through a dense canopy of palms and native foliage leads to this nearly five-acre peninsula property with expansive bay frontage and exceptional seclusion. Endless expanses of water and sky form a breathtaking backdrop, while the ever-shifting light throughout the day casts the home and acreage in a constantly evolving palette. Designed for multilevel living, the 6,891-square-foot home features the main living structure with separate wings connected by enclosed bridges. Walls of glass dissolve the boundaries between interior and landscape, revealing lush grounds and a brilliant bay panorama that unfolds endlessly toward the horizon. A beautifully crafted pool surrounds nearly half of the home’s exterior and mirrors the tranquil movement of the water beyond. Clean architectural lines, soaring interior volumes, and a thoughtful interplay of solid and transparent forms create a cohesive relationship between the interior and exterior. Ceilings reaching up to 21 feet allow natural light to move freely throughout the home. Every space reveals a considered balance of visual drama and functional design. With every turn, another exquisite detail reveals itself—thoughtfully composed, beautifully nuanced, and presented with quiet grandeur. As daylight fades, exterior lighting transforms the grounds into a resort-like setting, creating an inviting atmosphere where every gathering becomes a memorable experience. A private dock with two lifts provides direct access to the protected shoreline of Sarasota Bay and the Intracoastal Waterway, supporting a seamless boating lifestyle. An elevator serves the home’s multiple levels, while Lutron lighting and automated shades allow the residence to respond intuitively to changing daylight. The owner’s garage provides convenient access to the interior elevator and an additional air-conditioned four-bay garage with a generous workspace brings the total capacity to six vehicles. A whole-home generator provides added continuity and peace of mind. Impeccably maintained by its original owner, the residence reflects an uncommon level of care and stewardship. Estates of this size and caliber, architectural clarity, substantial waterfront, established boating infrastructure, development flexibility, and meticulously maintained condition are exceptionally rare. This impressive property exudes a sense of timelessness and is distinguished by its design, scale, privacy, and extraordinary location.

6610 Gulf Of Mexico Drive, Longboat Key

$2,693,000

From the moment you enter, the effect is unforgettable. Dramatic floor-to-ceiling windows create an immediate WOW factor, drawing your eye out to the tranquil canal, your own 55’ dock and expansive view of mangroves. An abundance of natural light and a sense of openness defines this special residence. Completely reimagined and extensively rebuilt inside and out between 2022 and 2026, this is far more than a traditional renovation. Every space reflects a thoughtful approach to contemporary design, with attention to details. From the stunning custom kitchen featuring sleek European-inspired cabinetry, Bosch appliances, quartz waterfall island to the sophisticated lighting, impact resistant windows and doors, wide-plank wood-look porcelain tile flooring throughout and beautifully updated bathrooms to the resort-style 34’ pool plus expansive covered outdoor entertaining area, a new metal roof, this distinctive property offers the appeal of contemporary luxury in one of Longboat Key’s most desirable island settings.

3 Beds ⋅ 2 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code

From the moment you enter, the effect is unforgettable. Dramatic floor-to-ceiling windows create an immediate WOW factor, drawing your eye out to the tranquil canal, your own 55’ dock and expansive view of mangroves. An abundance of natural light and a sense of openness defines this special residence. Completely reimagined and extensively rebuilt inside and out between 2022 and 2026, this is far more than a traditional renovation. Every space reflects a thoughtful approach to contemporary design, with attention to details. From the stunning custom kitchen featuring sleek European-inspired cabinetry, Bosch appliances, quartz waterfall island to the sophisticated lighting, impact resistant windows and doors, wide-plank wood-look porcelain tile flooring throughout and beautifully updated bathrooms to the resort-style 34’ pool plus expansive covered outdoor entertaining area, a new metal roof, this distinctive property offers the appeal of contemporary luxury in one of Longboat Key’s most desirable island settings.

660 Penfield Street, Longboat Key

$2,500,000

Nestled on the coveted north end of Longboat Key, this exceptional residence is tucked away on the secluded and private Lands End Drive, one of the island's most treasured addresses. Rich in history, Lands End is celebrated for its maritime heritage, world-class fishing, and preservation of Old Florida charm. With just twelve homes in this exclusive gated enclave, residents enjoy an unparalleled sense of privacy while embracing an effortless waterfront lifestyle. The community offers an impressive collection of amenities, including deep water boat slips on the open bay, a heated swimming pool, tennis and pickleball courts, and maintenance-free living—creating the ideal year-round residence or luxurious seasonal retreat. Surrounded by lush tropical landscaping, the home offers a series of serene outdoor living spaces, private terraces, and a waterfront dock, inviting you to enjoy peaceful mornings, spectacular sunsets, and endless days on the water. Elevated and thoughtfully designed on a single living level, the residence evokes the feeling of a sophisticated treehouse, with tranquil views through a canopy of tropical greenery. Inside, you are greeted with a dramatic great room that features soaring vaulted cedar-lined ceilings and exposed beams creating warmth and architectural character throughout the open-concept floor plan. Designed for both relaxed living and effortless entertaining, the home features three spacious bedrooms, three full baths, and a split floor plan that offers guests their own private wing, with two bedrooms opening directly onto terraces with atrium views. The separate library and a dedicated office, with custom built-in cabinetry, add distinctive character and are ideal for working remotely or pursuing creative passions. The island kitchen invites family gatherings, while the primary suite offers a full wall of windows over the bayou, dual walk-in closets, and additional custom storage. The expansive dual garages provide exceptional storage and accommodate up to four vehicles, with additional space for a golf cart, paddleboards, kayaks, bicycles, and all the essentials for embracing Longboat Key's laid-back coastal lifestyle. With pristine Gulf beaches just a short walk or golf cart ride away, this property offers the rare combination of historic island character, boating convenience, exceptional privacy, and maintenance-free ownership. This remarkable home is more than a residence—it is a sanctuary where every day feels like a vacation.

3 Beds ⋅ 3 Baths ⋅ Lands End SubDv. ⋅ 34228 Zip Code

Nestled on the coveted north end of Longboat Key, this exceptional residence is tucked away on the secluded and private Lands End Drive, one of the island's most treasured addresses. Rich in history, Lands End is celebrated for its maritime heritage, world-class fishing, and preservation of Old Florida charm. With just twelve homes in this exclusive gated enclave, residents enjoy an unparalleled sense of privacy while embracing an effortless waterfront lifestyle. The community offers an impressive collection of amenities, including deep water boat slips on the open bay, a heated swimming pool, tennis and pickleball courts, and maintenance-free living—creating the ideal year-round residence or luxurious seasonal retreat. Surrounded by lush tropical landscaping, the home offers a series of serene outdoor living spaces, private terraces, and a waterfront dock, inviting you to enjoy peaceful mornings, spectacular sunsets, and endless days on the water. Elevated and thoughtfully designed on a single living level, the residence evokes the feeling of a sophisticated treehouse, with tranquil views through a canopy of tropical greenery. Inside, you are greeted with a dramatic great room that features soaring vaulted cedar-lined ceilings and exposed beams creating warmth and architectural character throughout the open-concept floor plan. Designed for both relaxed living and effortless entertaining, the home features three spacious bedrooms, three full baths, and a split floor plan that offers guests their own private wing, with two bedrooms opening directly onto terraces with atrium views. The separate library and a dedicated office, with custom built-in cabinetry, add distinctive character and are ideal for working remotely or pursuing creative passions. The island kitchen invites family gatherings, while the primary suite offers a full wall of windows over the bayou, dual walk-in closets, and additional custom storage. The expansive dual garages provide exceptional storage and accommodate up to four vehicles, with additional space for a golf cart, paddleboards, kayaks, bicycles, and all the essentials for embracing Longboat Key's laid-back coastal lifestyle. With pristine Gulf beaches just a short walk or golf cart ride away, this property offers the rare combination of historic island character, boating convenience, exceptional privacy, and maintenance-free ownership. This remarkable home is more than a residence—it is a sanctuary where every day feels like a vacation.

677 Lands End Drive, Longboat Key

2012 Harbourside Drive Unit 2102, Longboat Key

$795,000

Experience the best of Longboat Key living in this spacious 2-bedroom, 2.5-bath condominium located in the gated Fairway Bay community of Bay Isles. Offering approximately 1,590 square feet of living space, this residence features a comfortable two-level layout, a bright Florida room, and an attached garage. Enjoy beautifully landscaped surroundings and an array of community amenities, including a swimming pool, spa, clubhouse, and tennis courts. Conveniently located near Sarasota Bay, local dining, shopping, and the beautiful Gulf beaches, this property offers an exceptional opportunity to enjoy the relaxed coastal lifestyle of Longboat Key. Just a short drive from St. Armands Circle and downtown Sarasota, this residence combines comfort, convenience, and an excellent island location.

2 Beds ⋅ 3 Baths ⋅ Bay Isles SubDv. ⋅ 34228 Zip Code

Experience the best of Longboat Key living in this spacious 2-bedroom, 2.5-bath condominium located in the gated Fairway Bay community of Bay Isles. Offering approximately 1,590 square feet of living space, this residence features a comfortable two-level layout, a bright Florida room, and an attached garage. Enjoy beautifully landscaped surroundings and an array of community amenities, including a swimming pool, spa, clubhouse, and tennis courts. Conveniently located near Sarasota Bay, local dining, shopping, and the beautiful Gulf beaches, this property offers an exceptional opportunity to enjoy the relaxed coastal lifestyle of Longboat Key. Just a short drive from St. Armands Circle and downtown Sarasota, this residence combines comfort, convenience, and an excellent island location.

2012 Harbourside Drive Unit 2102, Longboat Key

615 Dream Island Place Unit 212, Longboat Key

$1,089,000

Enjoy waterfront living in this very special home located in the Harbour Villa Club on Longboat Key. This second-floor end residence offers a truly open and unobstructed view of Sarasota Bay and comes with a deeded boat dock. A wall of impact-rated glass sliders enables you to enjoy the expansive Bay views throughout the open-concept floor plan, including from the living room, dining room, kitchen, and primary bedroom. All windows and doors are impact-rated. You'll marvel at the stunning experience of sunrise and sunset over the water from this exceptional setting. Offered fully furnished, this residence has been extensively renovated, including the kitchen, wet bar, bathrooms, flooring, closets, front door, and windows, creating a bright and comfortable coastal retreat. The modern open kitchen features quartz countertops, stainless steel appliances, and a striking tile backsplash, a breakfast bar with extra storage and a pantry closet. The adjoining wet bar adds both function and style for entertaining. The primary suite is generously proportioned with an ensuite bath that has a wall of lighted closets, dual sinks, a walk-in stone-surfaced shower with a rain head, and a separate water closet. An in-unit washer and dryer add convenience for the beach and boating life. A standout feature is the deeded boat dock with a 10,000-pound lift. Ideally positioned for added protection from the open waters of Sarasota Bay, the dock features low-maintenance Trex decking, along with water and electricity. For boating enthusiasts and serious fishing, you are less than 2 miles from Longboat Pass and the Gulf. A dock storage box is included. Harbour Villa Club offers a resort-style life with a stunning bayfront pool and spa, tennis and pickleball courts, boat ramp and kayak storage, all on beautifully maintained, tropical landscaped grounds. This home also includes a reserved covered parking space. There is plenty of guest parking for a second vehicle. There is also a temperature-controlled storage locker and reserved bicycle space for this home. With its waterfront setting, boating, and community amenities, this property offers the best of island living. It is also an attractive investment opportunity, with rentals permitted up to 52 times a year. Owners may also generate additional income by renting out the boat dock, subject to association rules.

2 Beds ⋅ 2 Baths ⋅ Harbour Villa Club At The Bucc SubDv. ⋅ 34228 Zip Code

Enjoy waterfront living in this very special home located in the Harbour Villa Club on Longboat Key. This second-floor end residence offers a truly open and unobstructed view of Sarasota Bay and comes with a deeded boat dock. A wall of impact-rated glass sliders enables you to enjoy the expansive Bay views throughout the open-concept floor plan, including from the living room, dining room, kitchen, and primary bedroom. All windows and doors are impact-rated. You'll marvel at the stunning experience of sunrise and sunset over the water from this exceptional setting. Offered fully furnished, this residence has been extensively renovated, including the kitchen, wet bar, bathrooms, flooring, closets, front door, and windows, creating a bright and comfortable coastal retreat. The modern open kitchen features quartz countertops, stainless steel appliances, and a striking tile backsplash, a breakfast bar with extra storage and a pantry closet. The adjoining wet bar adds both function and style for entertaining. The primary suite is generously proportioned with an ensuite bath that has a wall of lighted closets, dual sinks, a walk-in stone-surfaced shower with a rain head, and a separate water closet. An in-unit washer and dryer add convenience for the beach and boating life. A standout feature is the deeded boat dock with a 10,000-pound lift. Ideally positioned for added protection from the open waters of Sarasota Bay, the dock features low-maintenance Trex decking, along with water and electricity. For boating enthusiasts and serious fishing, you are less than 2 miles from Longboat Pass and the Gulf. A dock storage box is included. Harbour Villa Club offers a resort-style life with a stunning bayfront pool and spa, tennis and pickleball courts, boat ramp and kayak storage, all on beautifully maintained, tropical landscaped grounds. This home also includes a reserved covered parking space. There is plenty of guest parking for a second vehicle. There is also a temperature-controlled storage locker and reserved bicycle space for this home. With its waterfront setting, boating, and community amenities, this property offers the best of island living. It is also an attractive investment opportunity, with rentals permitted up to 52 times a year. Owners may also generate additional income by renting out the boat dock, subject to association rules.

615 Dream Island Place Unit 212, Longboat Key

775 Longboat Club Road Unit 304, Longboat Key

$1,295,000

At the southern tip of Longboat Key, just beyond the gated entrance to the Longboat Key Club, The Beaches is a premier gulf-front residence with resort-style amenities. Residents enjoy the private beach, 24-hour concierge service, two Har-Tru tennis courts, a heated beachfront pool and spa, a fitness center, and a club room with a catering kitchen. Unit 304 offers a split-bedroom floor plan and a wraparound terrace. From here, watch the sun rise over Sarasota Bay and the golf course, with partial Gulf views to the south and west. The fully updated interior features a gourmet kitchen with granite countertops, updated baths, and high-end flooring throughout. Windows and sliders are impact glass. The association has completed a number of improvements in recent years, including a new roof in March 2026. The quarterly HOA reflected in this listing is $10,075 for the last quarter of 2026 and is scheduled to decrease to $8,740 per quarter in 2027 (budget available upon request). If the private beach and pool are not enough, membership opportunities are available at the Longboat Key Club for Full Golf, Tennis, and Social categories. Here is your chance to have it all on the beach!

2 Beds ⋅ 2 Baths ⋅ Beaches Of Longboat Key SubDv. ⋅ 34228 Zip Code

At the southern tip of Longboat Key, just beyond the gated entrance to the Longboat Key Club, The Beaches is a premier gulf-front residence with resort-style amenities. Residents enjoy the private beach, 24-hour concierge service, two Har-Tru tennis courts, a heated beachfront pool and spa, a fitness center, and a club room with a catering kitchen. Unit 304 offers a split-bedroom floor plan and a wraparound terrace. From here, watch the sun rise over Sarasota Bay and the golf course, with partial Gulf views to the south and west. The fully updated interior features a gourmet kitchen with granite countertops, updated baths, and high-end flooring throughout. Windows and sliders are impact glass. The association has completed a number of improvements in recent years, including a new roof in March 2026. The quarterly HOA reflected in this listing is $10,075 for the last quarter of 2026 and is scheduled to decrease to $8,740 per quarter in 2027 (budget available upon request). If the private beach and pool are not enough, membership opportunities are available at the Longboat Key Club for Full Golf, Tennis, and Social categories. Here is your chance to have it all on the beach!

775 Longboat Club Road Unit 304, Longboat Key

738 Spanish Drive S Unit 98, Longboat Key

$495,000

Discover the best of Longboat Key living in this freestanding, well-maintained 2-bedroom, 1.5-bath freestanding villa in the sought-after Spanish Main Yacht Club. With about 1,200 sq ft of living space plus an enclosed Florida room, this light-filled home features plantation shutters, terrazzo flooring and an updated kitchen with wood cabinetry and granite counters. Outside, enjoy a covered carport, private entrance and a private back yard with added privacy, plus block construction and a tile roof. Spanish Main Yacht Club offers deeded private beach access, a heated community pool, clubhouse, shuffleboard, kayak storage and a 40-slip private marina — just a short stroll from Gulf sunsets and minutes from St. Armand's Circle and Sarasota dining and shopping. Buyer association approval required; leasing permitted with a one-month minimum, up to twice annually. Check out the videos of the home and the community now, then call for a tour!

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

Discover the best of Longboat Key living in this freestanding, well-maintained 2-bedroom, 1.5-bath freestanding villa in the sought-after Spanish Main Yacht Club. With about 1,200 sq ft of living space plus an enclosed Florida room, this light-filled home features plantation shutters, terrazzo flooring and an updated kitchen with wood cabinetry and granite counters. Outside, enjoy a covered carport, private entrance and a private back yard with added privacy, plus block construction and a tile roof. Spanish Main Yacht Club offers deeded private beach access, a heated community pool, clubhouse, shuffleboard, kayak storage and a 40-slip private marina — just a short stroll from Gulf sunsets and minutes from St. Armand's Circle and Sarasota dining and shopping. Buyer association approval required; leasing permitted with a one-month minimum, up to twice annually. Check out the videos of the home and the community now, then call for a tour!

738 Spanish Drive S Unit 98, Longboat Key

$595,000

Experience the best of Longboat Key waterfront living in this beautifully renovated corner condominium in Sutton Place, where modern coastal elegance meets breathtaking Sarasota Bay views. Offering 2 bedrooms, 2 bathrooms, and 1,148 square feet of thoughtfully redesigned living space, this residence captures sweeping water views from every room. Rarely available, a corner unit of this caliber offers an extraordinary opportunity to enjoy effortless waterfront living and explore the natural beauty of Longboat Key. Transformed with exceptional attention to detail, this light-filled home combines elevated finishes, soothing coastal palette, and an airy open-concept layout to create the ultimate coastal retreat. Luxury wood and tile accents compliment the redesigned interior, while the showcase kitchen features stunning water views, quartz countertops, European-style soft-close cabinetry, stainless steel appliances, stylish wine bar, and breakfast bar. Hurricane-impact windows and sliding glass doors provide peace of mind while framing waterfront vistas. The luxurious primary suite serves as an elevated retreat with bay views, custom walk-in wardrobe, and beautifully renovated en suite bath. The guest bedroom features wall-to-wall custom closet organization, while both bathrooms have been tastefully remodeled with designer tile-work, upgraded vanities, and premium fixtures. Additional improvements include luxury tile throughout, updated electrical and plumbing systems, new interior doors and hardware, recessed lighting, updated light fixtures and ceiling fans, new sinks, toilets, shelving, and custom closet systems. Extending the living space, the spacious Florida room is enclosed by floor-to-ceiling hurricane-impact sliding glass doors, creating a seamless connection between indoors and the spectacular waterfront setting. Perfectly positioned just steps from the bayfront heated community pool and marina, Sutton Place offers a Gulf Coast lifestyle that is truly unmatched. Residents enjoy exclusive private beach access directly across Gulf of Mexico Drive, complete with restrooms, showers, and convenient beach storage. Additional amenities include two sparkling swimming pools, affordable resident-only boat dockage with boat slips available on an as-available basis, an electric kayak launch and storage, and clubhouse. Thoughtfully improved for comfort, reliability, and peace of mind, the community has completed extensive improvements, including new roofs throughout, fresh exterior paint, and a resurfaced pool. The property has experienced no hurricane damage or flooding, and the community has successfully passed its milestone inspection with 10-year certification. The monthly HOA fee includes hazard, hurricane, and flood insurance, and reserves have been fully funded, adding another layer of financial reassurance for owners. An assigned covered parking space is conveniently located directly in front of the residence. Whether you're seeking a full-time residence, seasonal escape, or waterfront getaway, this impeccably renovated Sutton Place condominium delivers an exceptional combination of modern coastal luxury, thoughtful improvements, resort-style amenities, and the coveted Longboat Key lifestyle.

2 Beds ⋅ 2 Baths ⋅ Sutton Place Condo SubDv. ⋅ 34228 Zip Code

Experience the best of Longboat Key waterfront living in this beautifully renovated corner condominium in Sutton Place, where modern coastal elegance meets breathtaking Sarasota Bay views. Offering 2 bedrooms, 2 bathrooms, and 1,148 square feet of thoughtfully redesigned living space, this residence captures sweeping water views from every room. Rarely available, a corner unit of this caliber offers an extraordinary opportunity to enjoy effortless waterfront living and explore the natural beauty of Longboat Key. Transformed with exceptional attention to detail, this light-filled home combines elevated finishes, soothing coastal palette, and an airy open-concept layout to create the ultimate coastal retreat. Luxury wood and tile accents compliment the redesigned interior, while the showcase kitchen features stunning water views, quartz countertops, European-style soft-close cabinetry, stainless steel appliances, stylish wine bar, and breakfast bar. Hurricane-impact windows and sliding glass doors provide peace of mind while framing waterfront vistas. The luxurious primary suite serves as an elevated retreat with bay views, custom walk-in wardrobe, and beautifully renovated en suite bath. The guest bedroom features wall-to-wall custom closet organization, while both bathrooms have been tastefully remodeled with designer tile-work, upgraded vanities, and premium fixtures. Additional improvements include luxury tile throughout, updated electrical and plumbing systems, new interior doors and hardware, recessed lighting, updated light fixtures and ceiling fans, new sinks, toilets, shelving, and custom closet systems. Extending the living space, the spacious Florida room is enclosed by floor-to-ceiling hurricane-impact sliding glass doors, creating a seamless connection between indoors and the spectacular waterfront setting. Perfectly positioned just steps from the bayfront heated community pool and marina, Sutton Place offers a Gulf Coast lifestyle that is truly unmatched. Residents enjoy exclusive private beach access directly across Gulf of Mexico Drive, complete with restrooms, showers, and convenient beach storage. Additional amenities include two sparkling swimming pools, affordable resident-only boat dockage with boat slips available on an as-available basis, an electric kayak launch and storage, and clubhouse. Thoughtfully improved for comfort, reliability, and peace of mind, the community has completed extensive improvements, including new roofs throughout, fresh exterior paint, and a resurfaced pool. The property has experienced no hurricane damage or flooding, and the community has successfully passed its milestone inspection with 10-year certification. The monthly HOA fee includes hazard, hurricane, and flood insurance, and reserves have been fully funded, adding another layer of financial reassurance for owners. An assigned covered parking space is conveniently located directly in front of the residence. Whether you're seeking a full-time residence, seasonal escape, or waterfront getaway, this impeccably renovated Sutton Place condominium delivers an exceptional combination of modern coastal luxury, thoughtful improvements, resort-style amenities, and the coveted Longboat Key lifestyle.

605 Sutton Place Unit 101, Longboat Key

2141 Harbourside Drive Unit 1203, Longboat Key

$1,450,000

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. Note: All new impact-windows and doors. 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. Note: All new impact-windows and doors. 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

$1,250,000

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

$9,500,000

Behind the double-gated entry of Bay Isles’ coveted Harbor section, 560 Harbor Point commands a rare position at the end of a quiet cul-de-sac, with 200 feet of pristine, protected water frontage and breathtaking views of the downtown Sarasota skyline. Designed by acclaimed architect Clifford Scholz and meticulously crafted by Murray Homes, this 5,245-square-foot Palladian-style masterpiece pairs timeless architectural symmetry with the ease of true waterfront living. Inside, an exceptional floor plan unfolds across four luxurious bedroom suites and four and a half baths, with a formal living room, private dining room, family room, and a gourmet kitchen equipped for the finest culinary creations. His-and-hers offices offer the flexibility today’s discerning buyer expects, while impeccable millwork and the finest finishes reflect every detail executed to perfection. Expansive waterfront terraces and a redesigned viewing porch frame magical water views from every room. Outside, the water is the star. A private dock with boat lift and kayak launch puts the Gulf and Sarasota Bay within easy reach, with no bridges between you and open water. It is boating the way it was meant to be: quiet, private, and just steps from your back door. As a Bay Isles homeowner, you’ll also enjoy deeded, resident-only access to the Bay Isles Beach Club on the Gulf of Mexico, complete with an on-site attendant, covered gathering and picnic areas, changing rooms, barbecue grills, a volleyball court, and beach accessory storage. Close by are the championship golf, tennis, and dining of the Longboat Key Club, the St. Regis Resort, and the boutiques and restaurants of St. Armands Circle, while a short drive across the causeway brings downtown Sarasota’s acclaimed dining, vibrant arts scene, and beloved Farmers Market. Double-gated privacy. 200 feet of water frontage. Cul-de-sac seclusion. A rare offering in one of Longboat Key’s most prestigious enclaves.

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

Behind the double-gated entry of Bay Isles’ coveted Harbor section, 560 Harbor Point commands a rare position at the end of a quiet cul-de-sac, with 200 feet of pristine, protected water frontage and breathtaking views of the downtown Sarasota skyline. Designed by acclaimed architect Clifford Scholz and meticulously crafted by Murray Homes, this 5,245-square-foot Palladian-style masterpiece pairs timeless architectural symmetry with the ease of true waterfront living. Inside, an exceptional floor plan unfolds across four luxurious bedroom suites and four and a half baths, with a formal living room, private dining room, family room, and a gourmet kitchen equipped for the finest culinary creations. His-and-hers offices offer the flexibility today’s discerning buyer expects, while impeccable millwork and the finest finishes reflect every detail executed to perfection. Expansive waterfront terraces and a redesigned viewing porch frame magical water views from every room. Outside, the water is the star. A private dock with boat lift and kayak launch puts the Gulf and Sarasota Bay within easy reach, with no bridges between you and open water. It is boating the way it was meant to be: quiet, private, and just steps from your back door. As a Bay Isles homeowner, you’ll also enjoy deeded, resident-only access to the Bay Isles Beach Club on the Gulf of Mexico, complete with an on-site attendant, covered gathering and picnic areas, changing rooms, barbecue grills, a volleyball court, and beach accessory storage. Close by are the championship golf, tennis, and dining of the Longboat Key Club, the St. Regis Resort, and the boutiques and restaurants of St. Armands Circle, while a short drive across the causeway brings downtown Sarasota’s acclaimed dining, vibrant arts scene, and beloved Farmers Market. Double-gated privacy. 200 feet of water frontage. Cul-de-sac seclusion. A rare offering in one of Longboat Key’s most prestigious enclaves.

560 Harbor Point Road, 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

$456,789

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, Brand New carports within the past year and new doors and impact-rated windows throughout the community. The pool has just been resurfaced and has a brand new pump and heater. 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, Brand New carports within the past year and new doors and impact-rated windows throughout the community. The pool has just been resurfaced and has a brand new pump and heater. 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

1920 Harbourside Drive Unit 1003, Longboat Key

$624,900

Virtually Staged. Start your day with glowing sunrise views across Sarasota Bay from the living room, primary suite, and screened lanai, where the waterfront setting makes every moment feel like a retreat. Located within the gated waterfront enclave of Bay Isles, this spacious 2-bedroom, 2.5-bath townhome offers effortless island living with serene bay views and a flexible layout. Access to Bay Isles EXCLUSIVE Beach Club right across the street! The main living level is thoughtfully designed for everyday living and entertaining, featuring an open living and dining area complemented by a wood-burning fireplace. The kitchen offers ample space for casual meals and future customization. Large sliders extend the living space to a screened lanai overlooking the bay—an ideal spot to unwind or host guests. Hurricane shutters are already installed, offering added security and peace of mind. Upstairs, two well-proportioned bedroom suites each include private baths and walk-in closets, providing comfort and privacy for owners and guests alike. The primary suite is highlighted by a light-filled bath with an oversized soaking tub with jets and skylights above, creating a relaxing, spa-inspired atmosphere. A versatile loft area with additional skylights offers flexibility for a home office or gym, den, or reading space. On the ground level, an oversized two-car tandem garage delivers exceptional storage and functionality, with room for hobbies or a workshop. Residents of Fairway Bay enjoy a pet-friendly environment, professional on-site management, lushly landscaped walking and biking paths, and a private heated pool. Ownership also includes access to the exclusive Bay Isles Beach Club, a private Gulf-front amenity offering pavilion seating, tropical cabanas, grilling and picnic areas, beach storage, kitchen prep, and private restroom facilities. Ideally situated near the beaches, golf, dining, and shopping of Longboat Key, this townhome presents a rare opportunity to own in one of the island’s most established and desirable communities. Optional membership in the Longboat Key Club offers access, depending on membership category, to 45 holes of championship golf, more than 20 Har-Tru tennis courts, pickleball, multiple dining venues, private beach and pool facilities, a full-service spa, fitness and wellness facilities, member events, Marina Village and the Club’s deep-water marina.

2 Beds ⋅ 3 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code

Virtually Staged. Start your day with glowing sunrise views across Sarasota Bay from the living room, primary suite, and screened lanai, where the waterfront setting makes every moment feel like a retreat. Located within the gated waterfront enclave of Bay Isles, this spacious 2-bedroom, 2.5-bath townhome offers effortless island living with serene bay views and a flexible layout. Access to Bay Isles EXCLUSIVE Beach Club right across the street! The main living level is thoughtfully designed for everyday living and entertaining, featuring an open living and dining area complemented by a wood-burning fireplace. The kitchen offers ample space for casual meals and future customization. Large sliders extend the living space to a screened lanai overlooking the bay—an ideal spot to unwind or host guests. Hurricane shutters are already installed, offering added security and peace of mind. Upstairs, two well-proportioned bedroom suites each include private baths and walk-in closets, providing comfort and privacy for owners and guests alike. The primary suite is highlighted by a light-filled bath with an oversized soaking tub with jets and skylights above, creating a relaxing, spa-inspired atmosphere. A versatile loft area with additional skylights offers flexibility for a home office or gym, den, or reading space. On the ground level, an oversized two-car tandem garage delivers exceptional storage and functionality, with room for hobbies or a workshop. Residents of Fairway Bay enjoy a pet-friendly environment, professional on-site management, lushly landscaped walking and biking paths, and a private heated pool. Ownership also includes access to the exclusive Bay Isles Beach Club, a private Gulf-front amenity offering pavilion seating, tropical cabanas, grilling and picnic areas, beach storage, kitchen prep, and private restroom facilities. Ideally situated near the beaches, golf, dining, and shopping of Longboat Key, this townhome presents a rare opportunity to own in one of the island’s most established and desirable communities. Optional membership in the Longboat Key Club offers access, depending on membership category, to 45 holes of championship golf, more than 20 Har-Tru tennis courts, pickleball, multiple dining venues, private beach and pool facilities, a full-service spa, fitness and wellness facilities, member events, Marina Village and the Club’s deep-water marina.

1920 Harbourside Drive Unit 1003, Longboat Key

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