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Under Construction. PRE-AUCTION: Bidder registration deadline: 5 November. Rising on nearly two private Gulf-front acres, this visionary estate is poised to become one of the most architecturally significant residences conceived on Longboat Key. Designed by internationally acclaimed Sweet Sparkman Architecture & Interiors, the sculptural home pairs bold modern form with coastal sensitivity, framing uninterrupted Gulf views from a dramatic foyer, open great room, and sweeping terraces. Dual kitchens, a temperature-controlled wine cellar, dedicated space for a private cinema, and rooftop deck elevate daily living and grand-scale entertaining, while a guest house and pool house extend privacy and flexibility. Lush resort-style grounds unfold to a shimmering pool and spa. Offered at a pivotal stage of construction, the estate presents a rare chance to shape an enduring Gulf-front legacy.

11 Beds ⋅ 17 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code

Under Construction. PRE-AUCTION: Bidder registration deadline: 5 November. Rising on nearly two private Gulf-front acres, this visionary estate is poised to become one of the most architecturally significant residences conceived on Longboat Key. Designed by internationally acclaimed Sweet Sparkman Architecture & Interiors, the sculptural home pairs bold modern form with coastal sensitivity, framing uninterrupted Gulf views from a dramatic foyer, open great room, and sweeping terraces. Dual kitchens, a temperature-controlled wine cellar, dedicated space for a private cinema, and rooftop deck elevate daily living and grand-scale entertaining, while a guest house and pool house extend privacy and flexibility. Lush resort-style grounds unfold to a shimmering pool and spa. Offered at a pivotal stage of construction, the estate presents a rare chance to shape an enduring Gulf-front legacy.

5965 Gulf Of Mexico Drive, Longboat Key

3710 Gulf Of Mexico Drive Unit F2, Longboat Key

$475,000

Island Living at Its Finest – Brand New Home on Longboat Key. Welcome to Gulfshore of Longboat, a highly desirable waterfront co-op community offering private beach access, boat docks, and sweeping views of the Gulf of Mexico and Sarasota Bay. This beautifully built 2-bedroom home combines modern efficiency with relaxed coastal living. An outdoor bathroom with a shower is a wonderful convenience for those enjoying the pool or boating. Step inside to an open, sun-filled floor plan featuring soaring ceilings with tray accents in both the living room and the primary bedroom, creating a bright, spacious atmosphere throughout. The kitchen is designed for everyday comfort and entertaining, complete with a center island, hardwood shaker cabinetry with soft-close doors and drawers, and a full stainless appliance package including refrigerator with ice and water, range, dishwasher, microwave, and garbage disposal. Built to current HUD hurricane standards and Energy Star certified, the home offers peace of mind with 2x6 construction, upgraded insulation, and low-E vinyl windows for year-round comfort and efficiency. Enjoy mornings at the private beach, afternoons at the heated pool, and evenings watching sunsets over the water. The community clubhouse hosts regular activities, making it easy to relax and connect with neighbors in a friendly coastal setting. Whether you’re looking for a winter retreat or full-time residence, this move-in-ready island home delivers comfort, security, and the lifestyle Longboat Key is known for. No pets (except for service animals or emotional support animals with appropriate paperwork) or Rentals permitted. Schedule your private showing today and start living the Gulf Coast dream.

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

Island Living at Its Finest – Brand New Home on Longboat Key. Welcome to Gulfshore of Longboat, a highly desirable waterfront co-op community offering private beach access, boat docks, and sweeping views of the Gulf of Mexico and Sarasota Bay. This beautifully built 2-bedroom home combines modern efficiency with relaxed coastal living. An outdoor bathroom with a shower is a wonderful convenience for those enjoying the pool or boating. Step inside to an open, sun-filled floor plan featuring soaring ceilings with tray accents in both the living room and the primary bedroom, creating a bright, spacious atmosphere throughout. The kitchen is designed for everyday comfort and entertaining, complete with a center island, hardwood shaker cabinetry with soft-close doors and drawers, and a full stainless appliance package including refrigerator with ice and water, range, dishwasher, microwave, and garbage disposal. Built to current HUD hurricane standards and Energy Star certified, the home offers peace of mind with 2x6 construction, upgraded insulation, and low-E vinyl windows for year-round comfort and efficiency. Enjoy mornings at the private beach, afternoons at the heated pool, and evenings watching sunsets over the water. The community clubhouse hosts regular activities, making it easy to relax and connect with neighbors in a friendly coastal setting. Whether you’re looking for a winter retreat or full-time residence, this move-in-ready island home delivers comfort, security, and the lifestyle Longboat Key is known for. No pets (except for service animals or emotional support animals with appropriate paperwork) or Rentals permitted. Schedule your private showing today and start living the Gulf Coast dream.

3710 Gulf Of Mexico Drive Unit F2, Longboat Key

$1,499,000

*Gorgeous Canal Home Featuring A Huge 125x90 Ft.Lot! This Completely Remodeled Waterfront Property Offers 1,882 Sq. Ft. With An Open Concept Floor Plan*Spacious Bedrooms & A Large Bonus Room, Renovated Washrooms, A Single Car Garage And Outdoor Shower With Relaxing Hot Tub*This Home Can Easily Sleep 8-10! Enjoy The Ultimate Coastal Lifestyle With Access To Sarasota Bay Only 50 Yards Away, Perfect For Fishing, Cruising and Sunset Boating*Only a Few Minute Walk To Deeded Beach Access*Metal Roof (2022), Windows & Doors (2022), Jet Ski Lift*Walking Distance To Several Restaurants Including Lo Key, Harry's and Guppy's*An Easy Drive To Shore LBK, Euphemia Haye, Mar Vista Dockside, Anna Maria Island, St. Armands Circle and Downtown Sarasota*Situated Just Four Homes From Tarawitt Point On A Deep Water Canal, Come See This Perfect Waterfront Home*

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

*Gorgeous Canal Home Featuring A Huge 125x90 Ft.Lot! This Completely Remodeled Waterfront Property Offers 1,882 Sq. Ft. With An Open Concept Floor Plan*Spacious Bedrooms & A Large Bonus Room, Renovated Washrooms, A Single Car Garage And Outdoor Shower With Relaxing Hot Tub*This Home Can Easily Sleep 8-10! Enjoy The Ultimate Coastal Lifestyle With Access To Sarasota Bay Only 50 Yards Away, Perfect For Fishing, Cruising and Sunset Boating*Only a Few Minute Walk To Deeded Beach Access*Metal Roof (2022), Windows & Doors (2022), Jet Ski Lift*Walking Distance To Several Restaurants Including Lo Key, Harry's and Guppy's*An Easy Drive To Shore LBK, Euphemia Haye, Mar Vista Dockside, Anna Maria Island, St. Armands Circle and Downtown Sarasota*Situated Just Four Homes From Tarawitt Point On A Deep Water Canal, Come See This Perfect Waterfront Home*

825 Tarawitt Drive, Longboat Key

2600 Harbourside Drive Unit L-05, Longboat Key

$425,000

Ask an L-dock boater, they will tell you it’s the best dock in the marina. Slip is near the seawall, just a few flat steps to your parked vehicle with easy in/out access. A 68 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina. This slip is one of the very few slips at the marina with a direct view of the Sarasota cityscape and colorfully lit Ringling bridge. Unlike most slips here, this does not require purchase of membership in the Yacht Club saving you an initiation fee plus monthly fees.This deep-water marina offers direct access to Sarasota Bay and the ICW. The marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. The Marina has everything a boater could need. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 63 LOA, usable beam is 23 ft at the head of the slip. Bonus features of this slip: No club membership required Abundant navigation room for maneuvering and docking One of very few slips with Direct Sarasota City scape view Close to main clubhouse, showers and pool Close, but not too close to seawall

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

Ask an L-dock boater, they will tell you it’s the best dock in the marina. Slip is near the seawall, just a few flat steps to your parked vehicle with easy in/out access. A 68 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina. This slip is one of the very few slips at the marina with a direct view of the Sarasota cityscape and colorfully lit Ringling bridge. Unlike most slips here, this does not require purchase of membership in the Yacht Club saving you an initiation fee plus monthly fees.This deep-water marina offers direct access to Sarasota Bay and the ICW. The marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. The Marina has everything a boater could need. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 63 LOA, usable beam is 23 ft at the head of the slip. Bonus features of this slip: No club membership required Abundant navigation room for maneuvering and docking One of very few slips with Direct Sarasota City scape view Close to main clubhouse, showers and pool Close, but not too close to seawall

2600 Harbourside Drive Unit L-05, Longboat Key

775 Longboat Club Road Unit 401, Longboat Key

$1,395,000

Discover Coastal Elegance at The Beaches of Longboat Key! Nestled behind the renowned gated entrance of the Longboat Key Club, The Beaches offers an unparalleled Gulf-front retreat on one of Florida's most exclusive barrier islands. This stunning 4th-floor, 2-bedroom/2-bath residence boasts direct western exposure, delivering breathtaking, forever Gulf of Mexico views and spectacular sunsets that paint the sky in vibrant hues every evening. Step inside to find stylish, move-in-ready finishes, including brand-new porcelain tile flooring throughout the living areas and elegant marble in both bathrooms. The updated kitchen shines with fresh cabinetry, a new GE Profile refrigerator, and dishwasher—perfect for effortless entertaining or quiet evenings at home. The spacious living room and both bedrooms feature impact-resistant sliders that open to a private balcony, seamlessly blending indoor comfort with the soothing sights and sounds of the beach and surf just steps away. Residents enjoy an exceptional array of resort-style amenities: 24-hour concierge service for added security and convenience, Gulfside heated pool and spa, Modern fitness center, Two Har-Tru tennis courts, Social room with a full catering kitchen, Direct beach walkway with complimentary beach chairs (and often umbrellas) provided. Additional perks include two assigned parking spaces in the secure garage and a dedicated storage unit. Priced to impress in this highly sought-after community, this turnkey condo combines modern luxury, prime beachfront access, and the prestige of Longboat Key Club living—without requiring club membership. Opportunities like this rarely last long on Longboat Key. Don't miss your chance to own a slice of paradise—schedule your private showing today!

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

Discover Coastal Elegance at The Beaches of Longboat Key! Nestled behind the renowned gated entrance of the Longboat Key Club, The Beaches offers an unparalleled Gulf-front retreat on one of Florida's most exclusive barrier islands. This stunning 4th-floor, 2-bedroom/2-bath residence boasts direct western exposure, delivering breathtaking, forever Gulf of Mexico views and spectacular sunsets that paint the sky in vibrant hues every evening. Step inside to find stylish, move-in-ready finishes, including brand-new porcelain tile flooring throughout the living areas and elegant marble in both bathrooms. The updated kitchen shines with fresh cabinetry, a new GE Profile refrigerator, and dishwasher—perfect for effortless entertaining or quiet evenings at home. The spacious living room and both bedrooms feature impact-resistant sliders that open to a private balcony, seamlessly blending indoor comfort with the soothing sights and sounds of the beach and surf just steps away. Residents enjoy an exceptional array of resort-style amenities: 24-hour concierge service for added security and convenience, Gulfside heated pool and spa, Modern fitness center, Two Har-Tru tennis courts, Social room with a full catering kitchen, Direct beach walkway with complimentary beach chairs (and often umbrellas) provided. Additional perks include two assigned parking spaces in the secure garage and a dedicated storage unit. Priced to impress in this highly sought-after community, this turnkey condo combines modern luxury, prime beachfront access, and the prestige of Longboat Key Club living—without requiring club membership. Opportunities like this rarely last long on Longboat Key. Don't miss your chance to own a slice of paradise—schedule your private showing today!

775 Longboat Club Road Unit 401, Longboat Key

$2,900,000

Pre-Construction. To be built. Build your dream waterfront home on North Longboat Key! Discover an exceptional opportunity to create your custom coastal retreat on this build-to-suit lot with 120 feet of waterfront frontage. The property is primed for development, with a permit filed and anticipated approval. Included in the price are complete architectural plans by Sweet Sparkman Architecture and Interiors, renowned for their innovative designs that harmonize modern luxury with beauty of Florida's coastal landscapes. The thoughtfully designed floor plan ensures a seamless flow for everyday living and entertaining, capturing breathtaking water views from key living areas. Whether you’re relaxing indoors or going out to enjoy the vibrant outdoor spaces, this home has been envisioned to maximize its unparalleled waterfront location. Key features include a new seawall in 2023 that provides a solid foundation for waterfront living. Deeded beach access, just a short distance away, offers private enjoyment of pristine sandy shores on Longboat Key. Boating enthusiasts will appreciate the ample frontage for a dock and boat, providing easy access to Sarasota Bay and beyond. On sought-after North Longboat Key, the property offers proximity to acclaimed restaurants like Shore, Whitney’s and Mar Vista, ensuring dining and entertainment are always nearby. This is your chance to bring a remarkable vision to life in one of Florida’s desired locations. Schedule your private showing today and imagine the possibilities.

3 Beds ⋅ 5 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code

Pre-Construction. To be built. Build your dream waterfront home on North Longboat Key! Discover an exceptional opportunity to create your custom coastal retreat on this build-to-suit lot with 120 feet of waterfront frontage. The property is primed for development, with a permit filed and anticipated approval. Included in the price are complete architectural plans by Sweet Sparkman Architecture and Interiors, renowned for their innovative designs that harmonize modern luxury with beauty of Florida's coastal landscapes. The thoughtfully designed floor plan ensures a seamless flow for everyday living and entertaining, capturing breathtaking water views from key living areas. Whether you’re relaxing indoors or going out to enjoy the vibrant outdoor spaces, this home has been envisioned to maximize its unparalleled waterfront location. Key features include a new seawall in 2023 that provides a solid foundation for waterfront living. Deeded beach access, just a short distance away, offers private enjoyment of pristine sandy shores on Longboat Key. Boating enthusiasts will appreciate the ample frontage for a dock and boat, providing easy access to Sarasota Bay and beyond. On sought-after North Longboat Key, the property offers proximity to acclaimed restaurants like Shore, Whitney’s and Mar Vista, ensuring dining and entertainment are always nearby. This is your chance to bring a remarkable vision to life in one of Florida’s desired locations. Schedule your private showing today and imagine the possibilities.

720 Tarawitt Drive, Longboat Key

2800 Harbourside Drive Unit E-08, Longboat Key

$250,000

access on the south side of the pier! A 60 ft. x 21 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club.. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted for approval prior to entering the marina. Max length of vessel allowed is 55 LOA, usable beam is 19 ft at the head of the slip.

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

access on the south side of the pier! A 60 ft. x 21 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club.. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted for approval prior to entering the marina. Max length of vessel allowed is 55 LOA, usable beam is 19 ft at the head of the slip.

2800 Harbourside Drive Unit E-08, Longboat Key

$650,000

Tucked along one of Longboat Key’s most peaceful and naturally beautiful streets is 681 Gulf Bay Road, a 9,000-square-foot homesite. Positioned just moments from Sarasota Bay and the Gulf of Mexico, this prime island lot offers the rare opportunity to design and build a custom coastal home in a location where nature, privacy, and convenience coexist effortlessly. Set on a quiet residential street bordered by the 32-acre Joan M. Durante Park, this property offers immediate access to shaded walking trails, mangrove boardwalks, bayfront docks, and daily wildlife sightings. With deeded access to both the beach and the bay, you are within easy reach of Longboat Key’s white sand beaches and tranquil bay waters. At the entrance to the street, iconic island favorites like Euphemia Haye and The Haye Loft make impromptu dinners and sunset cocktails delightfully effortless. The lot provides flexibility for a thoughtfully designed primary residence or second home, with space for elevated construction, a private pool, outdoor entertaining areas, and lush tropical landscaping. Located between Anna Maria Island and St. Armands Circle, you’ll enjoy the perfect balance of quiet island living and access to shopping, dining, boating, and cultural attractions in Sarasota.

Bailey-Dobson SubDv. ⋅ 34228 Zip Code

Tucked along one of Longboat Key’s most peaceful and naturally beautiful streets is 681 Gulf Bay Road, a 9,000-square-foot homesite. Positioned just moments from Sarasota Bay and the Gulf of Mexico, this prime island lot offers the rare opportunity to design and build a custom coastal home in a location where nature, privacy, and convenience coexist effortlessly. Set on a quiet residential street bordered by the 32-acre Joan M. Durante Park, this property offers immediate access to shaded walking trails, mangrove boardwalks, bayfront docks, and daily wildlife sightings. With deeded access to both the beach and the bay, you are within easy reach of Longboat Key’s white sand beaches and tranquil bay waters. At the entrance to the street, iconic island favorites like Euphemia Haye and The Haye Loft make impromptu dinners and sunset cocktails delightfully effortless. The lot provides flexibility for a thoughtfully designed primary residence or second home, with space for elevated construction, a private pool, outdoor entertaining areas, and lush tropical landscaping. Located between Anna Maria Island and St. Armands Circle, you’ll enjoy the perfect balance of quiet island living and access to shopping, dining, boating, and cultural attractions in Sarasota.

681 Gulf Bay Road, Longboat Key

$1,275,000

One or more photo(s) has been virtually staged. MOTIVATED SELLER! Welcome to 550 De Narvaez Drive, a meticulously maintained WATERFRONT residence set on an ELEVATED 10,000 sq. ft. lot in the highly desirable Sleepy Lagoon neighborhood on the NORTH END of Longboat Key. This solid concrete block home has experienced NO FLOODING & NO STORM DAMAGE, offering exceptional peace of mind. Spanning 1,758 sq. ft., the light-filled interior features 3 SPACIOUS BEDROOMS and 2 beautifully RENOVATED BATHS. Generous room sizes, abundant natural light, and an inviting floor plan create a true sense of warmth throughout the home. The UPDATED KITCHEN and baths showcase contemporary finishes while maintaining comfort and functionality. Enjoy peaceful CANAL VIEWS with direct access to Sarasota Bay—perfect for boating enthusiasts and embracing the ultimate Florida waterfront lifestyle. NEW DOUBLE PANE IMPACT-RESISTANT WINDOWS and sliding glass doors provide enhanced protection and energy efficiency. Additional upgrades include NEWLY LINED PLUMBING PIPES and UPGRADED ATTIC INSULATION for lasting durability and comfort. Offered FULLY FURNISHED, all furnishings convey with the sale—making this a true TURNKEY opportunity. Simply bring your suitcase and start enjoying coastal living immediately. The expansive elevated lot offers ample space for outdoor entertaining, gardening, or FUTURE EXPANSION POTENTIAL. Ideally located near world-renown Gulf beaches with BEACH ACCESS, exclusive dining, boutique shopping, and recreational amenities, this exceptional property is well-suited as a primary residence, seasonal retreat, or investment opportunity. Schedule your private showing today and experience refined, worry-free waterfront living at its finest.

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

One or more photo(s) has been virtually staged. MOTIVATED SELLER! Welcome to 550 De Narvaez Drive, a meticulously maintained WATERFRONT residence set on an ELEVATED 10,000 sq. ft. lot in the highly desirable Sleepy Lagoon neighborhood on the NORTH END of Longboat Key. This solid concrete block home has experienced NO FLOODING & NO STORM DAMAGE, offering exceptional peace of mind. Spanning 1,758 sq. ft., the light-filled interior features 3 SPACIOUS BEDROOMS and 2 beautifully RENOVATED BATHS. Generous room sizes, abundant natural light, and an inviting floor plan create a true sense of warmth throughout the home. The UPDATED KITCHEN and baths showcase contemporary finishes while maintaining comfort and functionality. Enjoy peaceful CANAL VIEWS with direct access to Sarasota Bay—perfect for boating enthusiasts and embracing the ultimate Florida waterfront lifestyle. NEW DOUBLE PANE IMPACT-RESISTANT WINDOWS and sliding glass doors provide enhanced protection and energy efficiency. Additional upgrades include NEWLY LINED PLUMBING PIPES and UPGRADED ATTIC INSULATION for lasting durability and comfort. Offered FULLY FURNISHED, all furnishings convey with the sale—making this a true TURNKEY opportunity. Simply bring your suitcase and start enjoying coastal living immediately. The expansive elevated lot offers ample space for outdoor entertaining, gardening, or FUTURE EXPANSION POTENTIAL. Ideally located near world-renown Gulf beaches with BEACH ACCESS, exclusive dining, boutique shopping, and recreational amenities, this exceptional property is well-suited as a primary residence, seasonal retreat, or investment opportunity. Schedule your private showing today and experience refined, worry-free waterfront living at its finest.

550 De Narvaez Drive, Longboat Key

4720 Gulf Of Mexico Drive Unit Villa 2, Longboat Key

$585,000

Completely renovated two-bedroom and two-bathroom walkout (no stairs to take) on Longboat Key! Welcome to coastal luxury living in Windward Bay, one of Longboat Key's most sought-after waterfront communities. Perfectly positioned between the sparkling waters of Sarasota Bay and the pristine Gulf beaches, this completely renovated 2-bedroom, 2-bath villa offers an exceptional blend of modern elegance, resort-style amenities, and the coveted island lifestyle buyers dream about. Fully reimagined and rebuilt from the studs, this stunning residence showcases high-end craftsmanship and designer finishes throughout. Every detail has been thoughtfully upgraded, including brand-new electrical systems, plumbing, drywall, insulation, kitchen, bathrooms, fixtures, and finishes—providing the peace of mind and comfort of essentially new construction within an established waterfront community. The bright, open-concept floor plan is flooded with natural light and designed for effortless indoor-outdoor living. The beautifully appointed chef's kitchen flows seamlessly into the living and dining areas, creating an inviting space ideal for entertaining, seasonal gatherings, or everyday enjoyment. A dedicated 220-volt outlet offers convenient electric vehicle charging, adding modern functionality and future-ready convenience. One of the villa's most desirable features is its easy ground-level access with no stairs, making everyday living simple and accessible. Pet lovers will appreciate Windward Bay's generous pet-friendly policy allowing up to two pets, a rare and highly desirable amenity on Longboat Key. Step outside to your private patio retreat surrounded by lush tropical landscaping and mature greenery. Enjoy peaceful mornings with coffee, spectacular sunset skies, and relaxing evenings gathered around the fire pit just moments from beach access. The Gulf of Mexico is only steps away, offering endless opportunities for shelling, beach walks, swimming, paddleboarding, and breathtaking sunsets. Residents of Windward Bay enjoy an unmatched collection of resort-style amenities set across nearly 27 acres of beautifully maintained waterfront property, including: Three beach access points to the powdery sand beaches of Longboat Key. Nearly one-half mile of scenic waterfront walking paths and nature trails. Two heated swimming pools. Six tennis and pickleball courts. Fitness center, sauna, clubhouse, library, and social gathering spaces. Two private marinas with boat slips and jet ski slips (for rent and subject to availability). Private fishing pier with panoramic bay views. Kayak storage and launch areas. Outdoor grilling stations, fire pits, and waterfront gathering areas. Lush park-like grounds with mature tropical landscaping. Whether you're searching for a primary residence, seasonal retreat, second home, snowbird escape, waterfront villa, beach getaway, or investment opportunity, this move-in-ready residence offers an unparalleled combination of location, lifestyle, and value. Ideally located minutes to St. Armands Circle, Sarasota's vibrant arts and dining scene, championship golf courses, boating destinations, waterfront restaurants, and world-renowned Gulf Coast beaches, this exceptional property delivers the very best of Longboat Key living. Experience the ultimate in island living where luxury, comfort, boating, beach access, and resort-style amenities come together in one extraordinary coastal retreat.

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

Completely renovated two-bedroom and two-bathroom walkout (no stairs to take) on Longboat Key! Welcome to coastal luxury living in Windward Bay, one of Longboat Key's most sought-after waterfront communities. Perfectly positioned between the sparkling waters of Sarasota Bay and the pristine Gulf beaches, this completely renovated 2-bedroom, 2-bath villa offers an exceptional blend of modern elegance, resort-style amenities, and the coveted island lifestyle buyers dream about. Fully reimagined and rebuilt from the studs, this stunning residence showcases high-end craftsmanship and designer finishes throughout. Every detail has been thoughtfully upgraded, including brand-new electrical systems, plumbing, drywall, insulation, kitchen, bathrooms, fixtures, and finishes—providing the peace of mind and comfort of essentially new construction within an established waterfront community. The bright, open-concept floor plan is flooded with natural light and designed for effortless indoor-outdoor living. The beautifully appointed chef's kitchen flows seamlessly into the living and dining areas, creating an inviting space ideal for entertaining, seasonal gatherings, or everyday enjoyment. A dedicated 220-volt outlet offers convenient electric vehicle charging, adding modern functionality and future-ready convenience. One of the villa's most desirable features is its easy ground-level access with no stairs, making everyday living simple and accessible. Pet lovers will appreciate Windward Bay's generous pet-friendly policy allowing up to two pets, a rare and highly desirable amenity on Longboat Key. Step outside to your private patio retreat surrounded by lush tropical landscaping and mature greenery. Enjoy peaceful mornings with coffee, spectacular sunset skies, and relaxing evenings gathered around the fire pit just moments from beach access. The Gulf of Mexico is only steps away, offering endless opportunities for shelling, beach walks, swimming, paddleboarding, and breathtaking sunsets. Residents of Windward Bay enjoy an unmatched collection of resort-style amenities set across nearly 27 acres of beautifully maintained waterfront property, including: Three beach access points to the powdery sand beaches of Longboat Key. Nearly one-half mile of scenic waterfront walking paths and nature trails. Two heated swimming pools. Six tennis and pickleball courts. Fitness center, sauna, clubhouse, library, and social gathering spaces. Two private marinas with boat slips and jet ski slips (for rent and subject to availability). Private fishing pier with panoramic bay views. Kayak storage and launch areas. Outdoor grilling stations, fire pits, and waterfront gathering areas. Lush park-like grounds with mature tropical landscaping. Whether you're searching for a primary residence, seasonal retreat, second home, snowbird escape, waterfront villa, beach getaway, or investment opportunity, this move-in-ready residence offers an unparalleled combination of location, lifestyle, and value. Ideally located minutes to St. Armands Circle, Sarasota's vibrant arts and dining scene, championship golf courses, boating destinations, waterfront restaurants, and world-renowned Gulf Coast beaches, this exceptional property delivers the very best of Longboat Key living. Experience the ultimate in island living where luxury, comfort, boating, beach access, and resort-style amenities come together in one extraordinary coastal retreat.

4720 Gulf Of Mexico Drive Unit Villa 2, Longboat Key

775 Longboat Club Road Unit 808, Longboat Key

$2,145,000

Behind the gates of the Longboat Key Club, this exceptional residence at The Beaches captures sweeping, unobstructed views of the Gulf of Mexico and its pristine shoreline, where vivid sunsets paint the horizon each evening. Perched on the eighth floor, this coveted Star floor plan is ideally positioned as a spacious end residence, offering 2,122 square feet of thoughtfully designed living space with 3 bedrooms and 3 full baths. Walls of glass frame panoramic water vistas and invite natural light to pour into the main living areas. Newly installed impact-rated sliders enhance both storm protection and seamless indoor-outdoor living, while oak engineered hardwood flooring flows beautifully through the living room, dining area, and kitchen, creating a warm yet sophisticated coastal aesthetic. The generous layout provides an effortless blend of comfort and refinement, with well-proportioned bedrooms and baths designed to accommodate both everyday living and gracious entertaining. The Beaches is recognized as one of the premier beachfront addresses within the Longboat Key Club, offering direct access to the sugar-white sands and turquoise waters of the Gulf. Residents enjoy an elevated level of service and amenities, including a 24-hour concierge, resort-style pool, fitness center, tennis courts, and impeccably maintained grounds. Ideally located on the southern end of Longboat Key, this gated community affords convenient access to the fine dining and boutiques of St. Armands Circle, the vibrant arts and culture of downtown Sarasota, and the exclusive offerings of the Longboat Key Club. This is a rare opportunity to secure a front-row seat to the Gulf and embrace the effortless elegance of Florida’s most sought-after coastal lifestyle.

3 Beds ⋅ 3 Baths ⋅ Beaches Of Longboat Key SubDv. ⋅ 34228 Zip Code

Behind the gates of the Longboat Key Club, this exceptional residence at The Beaches captures sweeping, unobstructed views of the Gulf of Mexico and its pristine shoreline, where vivid sunsets paint the horizon each evening. Perched on the eighth floor, this coveted Star floor plan is ideally positioned as a spacious end residence, offering 2,122 square feet of thoughtfully designed living space with 3 bedrooms and 3 full baths. Walls of glass frame panoramic water vistas and invite natural light to pour into the main living areas. Newly installed impact-rated sliders enhance both storm protection and seamless indoor-outdoor living, while oak engineered hardwood flooring flows beautifully through the living room, dining area, and kitchen, creating a warm yet sophisticated coastal aesthetic. The generous layout provides an effortless blend of comfort and refinement, with well-proportioned bedrooms and baths designed to accommodate both everyday living and gracious entertaining. The Beaches is recognized as one of the premier beachfront addresses within the Longboat Key Club, offering direct access to the sugar-white sands and turquoise waters of the Gulf. Residents enjoy an elevated level of service and amenities, including a 24-hour concierge, resort-style pool, fitness center, tennis courts, and impeccably maintained grounds. Ideally located on the southern end of Longboat Key, this gated community affords convenient access to the fine dining and boutiques of St. Armands Circle, the vibrant arts and culture of downtown Sarasota, and the exclusive offerings of the Longboat Key Club. This is a rare opportunity to secure a front-row seat to the Gulf and embrace the effortless elegance of Florida’s most sought-after coastal lifestyle.

775 Longboat Club Road Unit 808, Longboat Key

$589,000

GORGEOUS COMPLETELY REMODELED Villa with Lake Views in Spanish Main Yacht Club!! Welcome to effortless coastal living in this beautifully remodeled 3-bedroom, 2-bath villa located in the highly sought-after Spanish Main Yacht Club. Rarely available, this 1,516 sq ft STANDALONE villa offers a larger footprint than most in the community and includes a true third bedroom with serene LAKE VIEWS. The recent remodel brings a fresh, modern feel, complemented by an open-concept floor plan, elegant tile flooring throughout, and abundant natural light. Enjoy peace of mind with NEW WATER HEATER, a NEWER ROOF (2023)AND NEWER A/C system (March 2024). Spanish Main Yacht Club offers a maintenance-free, pet-friendly community with resort-style amenities, including a large waterfront pool overlooking the marina, a 40-slip deep-water marina with no bridges to Sarasota Bay and the Gulf, and deeded beach access just steps away. Shopping, dining, and the charm of St. Armands Circle are all minutes from your door. While this is an active 55+ community, ownership is open to all ages, with full-time residency beginning at 50. "Florida remains the envy of the country, with many of our markets winning awards for being among the best places to live or retire. Sarasota SRQ Airport's soaring success added 30 flights in 2024 and 2025, significant passenger growth, a new $72M runway and terminal, and ranks No. 1 best resort airport in the country, where passengers can get off a plane and feel like their vacation has begun. It's all about investment. This home in the master-planned community of the Spanish Main Yacht Club could be your destination of choice. Features include a spectacular pool and spa, kayak launch, marina, outdoor grills, and lush tropical landscaping. There is a shell path for walking along to a deeded beach access to enjoy the sand and world-class sunsets. There is also on-site management and maintenance staff making where home and away share the same address. Longboat Key is the only barrier island on the West Coast of Florida to have relocated all overhead utilities underground for improved reliability and aesthetics, and LBK landed on the Forbes Travel Guide's list of Top 12 Destinations for 2025." Furniture Package Available. Schedule your private showing today.

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

GORGEOUS COMPLETELY REMODELED Villa with Lake Views in Spanish Main Yacht Club!! Welcome to effortless coastal living in this beautifully remodeled 3-bedroom, 2-bath villa located in the highly sought-after Spanish Main Yacht Club. Rarely available, this 1,516 sq ft STANDALONE villa offers a larger footprint than most in the community and includes a true third bedroom with serene LAKE VIEWS. The recent remodel brings a fresh, modern feel, complemented by an open-concept floor plan, elegant tile flooring throughout, and abundant natural light. Enjoy peace of mind with NEW WATER HEATER, a NEWER ROOF (2023)AND NEWER A/C system (March 2024). Spanish Main Yacht Club offers a maintenance-free, pet-friendly community with resort-style amenities, including a large waterfront pool overlooking the marina, a 40-slip deep-water marina with no bridges to Sarasota Bay and the Gulf, and deeded beach access just steps away. Shopping, dining, and the charm of St. Armands Circle are all minutes from your door. While this is an active 55+ community, ownership is open to all ages, with full-time residency beginning at 50. "Florida remains the envy of the country, with many of our markets winning awards for being among the best places to live or retire. Sarasota SRQ Airport's soaring success added 30 flights in 2024 and 2025, significant passenger growth, a new $72M runway and terminal, and ranks No. 1 best resort airport in the country, where passengers can get off a plane and feel like their vacation has begun. It's all about investment. This home in the master-planned community of the Spanish Main Yacht Club could be your destination of choice. Features include a spectacular pool and spa, kayak launch, marina, outdoor grills, and lush tropical landscaping. There is a shell path for walking along to a deeded beach access to enjoy the sand and world-class sunsets. There is also on-site management and maintenance staff making where home and away share the same address. Longboat Key is the only barrier island on the West Coast of Florida to have relocated all overhead utilities underground for improved reliability and aesthetics, and LBK landed on the Forbes Travel Guide's list of Top 12 Destinations for 2025." Furniture Package Available. Schedule your private showing today.

563 Spanish Drive S, Longboat Key

$1,025,000

Exceptional opportunity to acquire a canal-front homesite in the highly desirable community of Longboat Key. This property offers 129 feet of canal frontage, deeded beach access to white sand beaches of the Gulf, and a recently issued building permit for a custom single-family residence. Property improvements include an upgraded seawall, boat dock, pool structure, water connection, geotechnical study, and complete land and building surveys. Direct boating access to Sarasota Bay and the Gulf makes this an ideal location for boating enthusiasts. Permitted architectural and engineering plans are included for a custom-designed residence totaling 3,132 square feet under air, allowing construction to begin immediately. The design features 4 bedrooms, 4.5 bathrooms, open floor plan, outdoor lanai, 2 balconies, canal-facing terrace, and a 2-car garage. The balconies are perfectly positioned to capture sunrises over Sarasota Bay and stunning sunsets over the Gulf. Buyers may use the existing permitted plans or design a new residence subject to new permitting process. This listing is for the lot and permitted plans only; construction is not included in the list's price. Building cost estimates for the permitted design are available upon request. Conveniently located near Longboat Key's north-end within walking distance to several favorite restaurants, shops, and within close proximity to luxuries at St. Regis Longboat Key Resort and to golf, tennis, pickleball, boating, fishing, St. Armands Circle, and Anna Maria Island. This property offers a rare opportunity to build a custom waterfront residence in one of Florida's prestigious and premier barrier island.

Longboat Key SubDv. ⋅ 34228 Zip Code

Exceptional opportunity to acquire a canal-front homesite in the highly desirable community of Longboat Key. This property offers 129 feet of canal frontage, deeded beach access to white sand beaches of the Gulf, and a recently issued building permit for a custom single-family residence. Property improvements include an upgraded seawall, boat dock, pool structure, water connection, geotechnical study, and complete land and building surveys. Direct boating access to Sarasota Bay and the Gulf makes this an ideal location for boating enthusiasts. Permitted architectural and engineering plans are included for a custom-designed residence totaling 3,132 square feet under air, allowing construction to begin immediately. The design features 4 bedrooms, 4.5 bathrooms, open floor plan, outdoor lanai, 2 balconies, canal-facing terrace, and a 2-car garage. The balconies are perfectly positioned to capture sunrises over Sarasota Bay and stunning sunsets over the Gulf. Buyers may use the existing permitted plans or design a new residence subject to new permitting process. This listing is for the lot and permitted plans only; construction is not included in the list's price. Building cost estimates for the permitted design are available upon request. Conveniently located near Longboat Key's north-end within walking distance to several favorite restaurants, shops, and within close proximity to luxuries at St. Regis Longboat Key Resort and to golf, tennis, pickleball, boating, fishing, St. Armands Circle, and Anna Maria Island. This property offers a rare opportunity to build a custom waterfront residence in one of Florida's prestigious and premier barrier island.

600 Jungle Queen Way, Longboat Key

2450 Harbourside Drive Unit 234, Longboat Key

$1,800,000

Welcome to Marina Bay, one of the most coveted condominium residences within the guard-gated Bay Isles community on Longboat Key. This expansive three-bedroom, three-bath residence offers 3,383 square feet of light-filled living space and exceptional privacy, sharing the floor with only one other residence. Enjoy sweeping panoramic views of Sarasota Bay and downtown Sarasota from the oversized screened balcony—an ideal setting for morning coffee, evening relaxation, and watching the abundant birdlife and marine activity. A second west-facing balcony captures spectacular Gulf sunsets, offering the best of both sunrise and sunset living. Marina Bay delivers a true resort-style lifestyle, featuring a large heated pool, tennis courts, pickleball courts, and a fitness center. Take leisurely strolls along the neighboring marina or around the picturesque Longboat Key Club Harbourside Golf Course. Ideally located, this residence is just a half-mile walk to Publix, CVS, and local shops, and only one mile from the new St. Regis Longboat Key Resort. Membership to the Longboat Key Club is available separately, providing access to world-class golf, dining, tennis, pickleball, and beach amenities. Whether as a full-time residence or an exceptional vacation retreat, this is a rare opportunity to enjoy luxury, convenience, and resort living on Longboat Key—truly, the best of island life.

3 Beds ⋅ 3 Baths ⋅ Marina Bay SubDv. ⋅ 34228 Zip Code

Welcome to Marina Bay, one of the most coveted condominium residences within the guard-gated Bay Isles community on Longboat Key. This expansive three-bedroom, three-bath residence offers 3,383 square feet of light-filled living space and exceptional privacy, sharing the floor with only one other residence. Enjoy sweeping panoramic views of Sarasota Bay and downtown Sarasota from the oversized screened balcony—an ideal setting for morning coffee, evening relaxation, and watching the abundant birdlife and marine activity. A second west-facing balcony captures spectacular Gulf sunsets, offering the best of both sunrise and sunset living. Marina Bay delivers a true resort-style lifestyle, featuring a large heated pool, tennis courts, pickleball courts, and a fitness center. Take leisurely strolls along the neighboring marina or around the picturesque Longboat Key Club Harbourside Golf Course. Ideally located, this residence is just a half-mile walk to Publix, CVS, and local shops, and only one mile from the new St. Regis Longboat Key Resort. Membership to the Longboat Key Club is available separately, providing access to world-class golf, dining, tennis, pickleball, and beach amenities. Whether as a full-time residence or an exceptional vacation retreat, this is a rare opportunity to enjoy luxury, convenience, and resort living on Longboat Key—truly, the best of island life.

2450 Harbourside Drive Unit 234, Longboat Key

$12,900,000

Welcome to a once-in-a-generation private waterfront family compound on the coveted north end of Longboat Key—an extraordinary 2.4 acre, fully gated coastal estate that blends architectural mastery, resort-level amenities, and rare development potential. Encompassing four buildable parcels (500, 510, 520 Nomas Way and 6680 Gulf of Mexico Drive), this legacy property offers unparalleled privacy, flexibility, and long-term value. From the moment you arrive, illuminated by classic Bevelo gas lanterns, the estate unfolds with intention and elegance. The custom-designed main residence is complemented by a separate 3-bedroom, 2-bath, 1,850-sq-ft guest home with a detached garage—perfect for extended family, guests, or staff accommodations. Every detail reflects thoughtful craftsmanship, from the 900-bottle red cedar wine cellar to the oversized custom wood-burning fireplace with gas option. Designed for both grand entertaining and everyday indulgence, the chef’s kitchen features natural gas cooking with Wolf and Sub-Zero appliances, while state-of-the-art home automation and whole-home sound elevate daily living. Step outside to a true private resort: a 15,000-gallon free-form pool with a 1,000-gallon spa, heating and chilling via reverse heat pump and natural gas, and an expansive custom tiki pavilion built for unforgettable gatherings. For boating enthusiasts, this estate is unmatched—165 feet of frontage on Bishops Bayou, two docks, three boat lifts, and deep-water, direct Intracoastal access. Across Gulf of Mexico Drive, deeded private beach access makes turquoise waters and nightly sunsets a daily ritual. Car collectors and hobbyists will appreciate six garages, including an automotive lift, plus a 50’ x 24’ covered pole barn for additional storage. Peace of mind is absolute with a 24-camera security system, safe room, elevator, and a 60kW natural gas generator powering the entire estate during any weather event. Fully fenced and gated, this property offers complete privacy without compromise. This is more than a home—it is a coastal masterpiece, a designer’s dream that exudes sophistication, balance, and harmony. An irreplaceable opportunity to own one of Longboat Key’s most remarkable waterfront estates, where luxury, security, and lifestyle converge in perfect alignment.

6 Beds ⋅ 7 Baths ⋅ Rauch Subdivision SubDv. ⋅ 34228 Zip Code

Welcome to a once-in-a-generation private waterfront family compound on the coveted north end of Longboat Key—an extraordinary 2.4 acre, fully gated coastal estate that blends architectural mastery, resort-level amenities, and rare development potential. Encompassing four buildable parcels (500, 510, 520 Nomas Way and 6680 Gulf of Mexico Drive), this legacy property offers unparalleled privacy, flexibility, and long-term value. From the moment you arrive, illuminated by classic Bevelo gas lanterns, the estate unfolds with intention and elegance. The custom-designed main residence is complemented by a separate 3-bedroom, 2-bath, 1,850-sq-ft guest home with a detached garage—perfect for extended family, guests, or staff accommodations. Every detail reflects thoughtful craftsmanship, from the 900-bottle red cedar wine cellar to the oversized custom wood-burning fireplace with gas option. Designed for both grand entertaining and everyday indulgence, the chef’s kitchen features natural gas cooking with Wolf and Sub-Zero appliances, while state-of-the-art home automation and whole-home sound elevate daily living. Step outside to a true private resort: a 15,000-gallon free-form pool with a 1,000-gallon spa, heating and chilling via reverse heat pump and natural gas, and an expansive custom tiki pavilion built for unforgettable gatherings. For boating enthusiasts, this estate is unmatched—165 feet of frontage on Bishops Bayou, two docks, three boat lifts, and deep-water, direct Intracoastal access. Across Gulf of Mexico Drive, deeded private beach access makes turquoise waters and nightly sunsets a daily ritual. Car collectors and hobbyists will appreciate six garages, including an automotive lift, plus a 50’ x 24’ covered pole barn for additional storage. Peace of mind is absolute with a 24-camera security system, safe room, elevator, and a 60kW natural gas generator powering the entire estate during any weather event. Fully fenced and gated, this property offers complete privacy without compromise. This is more than a home—it is a coastal masterpiece, a designer’s dream that exudes sophistication, balance, and harmony. An irreplaceable opportunity to own one of Longboat Key’s most remarkable waterfront estates, where luxury, security, and lifestyle converge in perfect alignment.

6680 Gulf Of Mexico Drive, Longboat Key

$900,000

Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value.. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.

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

Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value.. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.

578 - 580 Companion Way, Longboat Key

$1,050,000

Virtually Staged. Situated on an expansive 11,250-square-foot lot, this property offers the perfect canvas to either remodel the existing home into a modern retreat or design a custom coastal estate from the ground up. The oversized lot provides ample room to create a private outdoor oasis, complete with a large pool, while enjoying a deep-water dock that is just seconds from the open water. Located just a short walk from some of the world’s most renowned white-sand beaches and only minutes from the charming shops and restaurants of the island, this property represents the ultimate blend of lifestyle and potential. Don’t miss this chance to own a piece of paradise and build your legacy on the water. Schedule your private tour today to explore the endless possibilities this rare site has to offer!

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

Virtually Staged. Situated on an expansive 11,250-square-foot lot, this property offers the perfect canvas to either remodel the existing home into a modern retreat or design a custom coastal estate from the ground up. The oversized lot provides ample room to create a private outdoor oasis, complete with a large pool, while enjoying a deep-water dock that is just seconds from the open water. Located just a short walk from some of the world’s most renowned white-sand beaches and only minutes from the charming shops and restaurants of the island, this property represents the ultimate blend of lifestyle and potential. Don’t miss this chance to own a piece of paradise and build your legacy on the water. Schedule your private tour today to explore the endless possibilities this rare site has to offer!

834 Jungle Queen Way, Longboat Key

$900,000

Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.

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

Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.

578 Companion Way, Longboat Key

26OO Harbourside Drive Unit O-06, Longboat Key

$265,000

A great view of the bay and city skyline along with easy boat access! This 50 x 20 foot slip at Longboat Key Club Moorings is located on the south side of O-dock. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and on-site concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 45 LOA; beam depends on the vessel. Call for more information.

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

A great view of the bay and city skyline along with easy boat access! This 50 x 20 foot slip at Longboat Key Club Moorings is located on the south side of O-dock. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and on-site concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 45 LOA; beam depends on the vessel. Call for more information.

26OO Harbourside Drive Unit O-06, Longboat Key

$1,645,000

Beautiful lot on one of the most desirable streets on north Longboat Key with a very wide canal that leads directly to Sarasota Bay and the intracoastal waterway. Emerald Harbour is right off Gulf of Mexico Dr . Close to Beautiful Lbk beach, restaurants, and shopping. Build your Florida dream home and enjoy, boating, fishing and the Beach.

Emerald Harbor SubDv. ⋅ 34228 Zip Code

Beautiful lot on one of the most desirable streets on north Longboat Key with a very wide canal that leads directly to Sarasota Bay and the intracoastal waterway. Emerald Harbour is right off Gulf of Mexico Dr . Close to Beautiful Lbk beach, restaurants, and shopping. Build your Florida dream home and enjoy, boating, fishing and the Beach.

721 Emerald Harbor Drive, Longboat Key

1211 Gulf Of Mexico Drive Unit 403, Longboat Key

$1,695,000

Escape to elegance in this tastefully renovated, fully furnished fourth-floor residence at The Promenade on Longboat Key, where luxury meets effortless coastal living. This spacious two-bedroom, two-bath split-floor-plan condo offers breathtaking sunset views overlooking the Gulf of Mexico and beautifully landscaped community grounds. Inside, no detail has been overlooked. The residence features Café Series appliances, Quartzite countertops in the kitchen and primary bath, custom cabinetry with a hidden vent hood, and Luminette motorized blinds throughout. Spa-like bathrooms showcase mosaic glass tile showers, rain showerheads, and Delta Premier fixtures, while large-plank luxury vinyl flooring flows seamlessly through the home. Additional highlights include an Electrolux washer and dryer, designer-finished balcony tiles, and impeccably curated furnishings that complete this turnkey offering. Set on 6.5 acres of Gulf-front paradise, The Promenade delivers an exceptional amenity lifestyle with four Har-Tru tennis courts, a beachfront gazebo, pool and spa, and men’s and women’s health clubs. Residents also enjoy two elegant party rooms, concierge services, an on-site manager, and 24/7 gated security, offering both luxury and peace of mind. Ideally located on the south end of Longboat Key, this residence is minutes from world-class dining, shopping, cultural venues, and medical facilities. Sarasota-Bradenton International Airport is just 20 minutes away, while Sarasota’s renowned attractions—including St. Armands Circle, The Ringling Museum, and Mote Marine Aquarium are easily accessible. Whether you seek serene beachfront living or vibrant coastal experiences, this is more than a home it’s a lifestyle. Welcome to your personal paradise at The Promenade.

2 Beds ⋅ 2 Baths ⋅ Promenade SubDv. ⋅ 34228 Zip Code

Escape to elegance in this tastefully renovated, fully furnished fourth-floor residence at The Promenade on Longboat Key, where luxury meets effortless coastal living. This spacious two-bedroom, two-bath split-floor-plan condo offers breathtaking sunset views overlooking the Gulf of Mexico and beautifully landscaped community grounds. Inside, no detail has been overlooked. The residence features Café Series appliances, Quartzite countertops in the kitchen and primary bath, custom cabinetry with a hidden vent hood, and Luminette motorized blinds throughout. Spa-like bathrooms showcase mosaic glass tile showers, rain showerheads, and Delta Premier fixtures, while large-plank luxury vinyl flooring flows seamlessly through the home. Additional highlights include an Electrolux washer and dryer, designer-finished balcony tiles, and impeccably curated furnishings that complete this turnkey offering. Set on 6.5 acres of Gulf-front paradise, The Promenade delivers an exceptional amenity lifestyle with four Har-Tru tennis courts, a beachfront gazebo, pool and spa, and men’s and women’s health clubs. Residents also enjoy two elegant party rooms, concierge services, an on-site manager, and 24/7 gated security, offering both luxury and peace of mind. Ideally located on the south end of Longboat Key, this residence is minutes from world-class dining, shopping, cultural venues, and medical facilities. Sarasota-Bradenton International Airport is just 20 minutes away, while Sarasota’s renowned attractions—including St. Armands Circle, The Ringling Museum, and Mote Marine Aquarium are easily accessible. Whether you seek serene beachfront living or vibrant coastal experiences, this is more than a home it’s a lifestyle. Welcome to your personal paradise at The Promenade.

1211 Gulf Of Mexico Drive Unit 403, Longboat Key

4835 Gulf Of Mexico Drive Unit 106, Longboat Key

$675,000

Waterfront Living on Longboat Key – Direct Gulf Access Experience the best of coastal living on beautiful Longboat Key. This first-floor residence offers effortless access and an unbeatable connection to the water, with direct access to the stunning Gulf of Mexico just steps from your door. Recently updated, the home features brand-new flooring throughout, along with all-new hurricane-impact windows, sliding glass doors, and a hurricane front door—providing peace of mind and modern comfort. Enjoy seamless indoor-outdoor living with easy walk-out access, perfect for morning beach strolls, sunset views, or simply embracing the relaxed Gulf Coast lifestyle. Whether you’re looking for a full-time residence, vacation getaway, or investment opportunity, this property offers exceptional value in a highly sought-after location. Year after year, The Westchester has been considered to be the most sought after location on Gulf of Mexico Drive. This two bedroom, two bath 1,393 sq. ft. condominium holds many family memories, which could now be yours. Experience the beautiful views of the Emerald waters from both lanais. Unit has recently been completely painted. Unit is move-in ready to be enjoyed! Both bathrooms contain generous walk-in closets, with a washer/dryer installed in the guest closet. Come witness Resort Style amenities of two heated pools, beach cabanas, car wash station, a tennis and pickleball court, shuffleboard court, kayak rack, outdoor storage and a welcoming grilling convenience behind Club 72. This split plan, first floor, master en-suite unit awaits your TLC. Kitchen includes side-by-side beverage refrigerators. R&R IS THE PACE, LBK IS THE PLACE!!!!!

2 Beds ⋅ 2 Baths ⋅ Westchester Condo Apts SubDv. ⋅ 34228 Zip Code

Waterfront Living on Longboat Key – Direct Gulf Access Experience the best of coastal living on beautiful Longboat Key. This first-floor residence offers effortless access and an unbeatable connection to the water, with direct access to the stunning Gulf of Mexico just steps from your door. Recently updated, the home features brand-new flooring throughout, along with all-new hurricane-impact windows, sliding glass doors, and a hurricane front door—providing peace of mind and modern comfort. Enjoy seamless indoor-outdoor living with easy walk-out access, perfect for morning beach strolls, sunset views, or simply embracing the relaxed Gulf Coast lifestyle. Whether you’re looking for a full-time residence, vacation getaway, or investment opportunity, this property offers exceptional value in a highly sought-after location. Year after year, The Westchester has been considered to be the most sought after location on Gulf of Mexico Drive. This two bedroom, two bath 1,393 sq. ft. condominium holds many family memories, which could now be yours. Experience the beautiful views of the Emerald waters from both lanais. Unit has recently been completely painted. Unit is move-in ready to be enjoyed! Both bathrooms contain generous walk-in closets, with a washer/dryer installed in the guest closet. Come witness Resort Style amenities of two heated pools, beach cabanas, car wash station, a tennis and pickleball court, shuffleboard court, kayak rack, outdoor storage and a welcoming grilling convenience behind Club 72. This split plan, first floor, master en-suite unit awaits your TLC. Kitchen includes side-by-side beverage refrigerators. R&R IS THE PACE, LBK IS THE PLACE!!!!!

4835 Gulf Of Mexico Drive Unit 106, Longboat Key

1065 Gulf Of Mexico Drive Unit 305, Longboat Key

$1,199,000

One or more photo(s) has been virtually staged. 3 BEDROOM CORNER/ END RESIDENCE! SOUTHWEST GULF VIEW! 2 OWNED PARKING SPACES- ONE COVERED! EXCELLENT RENTAL POTENTIAL! A vivid palette of white perfected with the backdrop of Gulf waters kissed by brilliant hues amid spanning skies as the sun sets on yet another perfect day. Yours to be experienced daily, from the bright inside or out on the patios, of this corner home spread over more than 1,800 square feet. Well-positioned at the southwest corner of Building 10 to take full advantage of what it means to be the fortunate owner of a beachfront Longboat Key retreat. Clean, crisp and white, this home is move-in ready, OR it is fresh and primed for you to begin the design of your dreams. Finding 3 bedrooms, 2 baths, and 2 owned parking spaces (one under-building and one outside steps to the building entry) on the beach at this reasonable price point is a FIND in this zip code, so closely consider the opportunity at hand. Beachplace is a sprawling community of 31 acres and full of amenities including, but not limited to, deeded beach access, junior Olympic size pool, kiddie pool, spa, clubhouse, fitness, tennis, pickleball, guarded/ gated entry, community grilling, fun gaming area with ping pong, cornhole, seasonal community activity calendar, etc. Truly a special place to call home or an absolute escape to refresh, restore, relax, release and renew the wellbeing of mind, body and spirit.

3 Beds ⋅ 2 Baths ⋅ Beachplace SubDv. ⋅ 34228 Zip Code

One or more photo(s) has been virtually staged. 3 BEDROOM CORNER/ END RESIDENCE! SOUTHWEST GULF VIEW! 2 OWNED PARKING SPACES- ONE COVERED! EXCELLENT RENTAL POTENTIAL! A vivid palette of white perfected with the backdrop of Gulf waters kissed by brilliant hues amid spanning skies as the sun sets on yet another perfect day. Yours to be experienced daily, from the bright inside or out on the patios, of this corner home spread over more than 1,800 square feet. Well-positioned at the southwest corner of Building 10 to take full advantage of what it means to be the fortunate owner of a beachfront Longboat Key retreat. Clean, crisp and white, this home is move-in ready, OR it is fresh and primed for you to begin the design of your dreams. Finding 3 bedrooms, 2 baths, and 2 owned parking spaces (one under-building and one outside steps to the building entry) on the beach at this reasonable price point is a FIND in this zip code, so closely consider the opportunity at hand. Beachplace is a sprawling community of 31 acres and full of amenities including, but not limited to, deeded beach access, junior Olympic size pool, kiddie pool, spa, clubhouse, fitness, tennis, pickleball, guarded/ gated entry, community grilling, fun gaming area with ping pong, cornhole, seasonal community activity calendar, etc. Truly a special place to call home or an absolute escape to refresh, restore, relax, release and renew the wellbeing of mind, body and spirit.

1065 Gulf Of Mexico Drive Unit 305, Longboat Key

4127 Gulf Of Mexico Drive Unit N102, Longboat Key

$4,700,000

Spectacular Gulf of Mexico views define this exceptional three-bedroom, three-and-a-half-bath residence that lives like a single-family home. A large wraparound terrace with a built-in grill offers seamless indoor-outdoor living, and private steps leading directly to the sandy beach – perfect for sunset entertaining or morning walks along the shore. Enter the home through a private elevator into a formal foyer with double door entry into the residence. The gracious living room is framed by expansive windows showcasing endless water views and exceptional sunsets flowing effortlessly to a built-in wet bar complete with wine refrigerator, ice maker, and a dedicated desk area—ideal for entertaining or casual work-from-home moments. A formal dining room with elegant ceiling detail makes hosting a dinner party a treat. Plantation shutters throughout the residence add a coastal and private touch. The gourmet kitchen is designed for both function and style, offering a large island for gathering, side-by-side Sub-Zero refrigerator and freezer, Wolf gas cooktop, Wolf oven with warming drawer, generous pantry, and a cozy desk area for browsing favorite recipes. A large center island and charming breakfast nook are the perfect spots for morning coffee or casual meals. Adjacent to the kitchen, the inviting keeping room opens to a private east-facing terrace with beautiful sunrise and views of Sarasota Bay. The expansive owner’s suite is a true retreat, featuring its own breakfast bar with sink and refrigerator for enjoying morning coffee while overlooking the Gulf. Two oversized, custom-built walk-in closets provide exceptional storage. The spa-inspired bath includes double vanities, a glass-enclosed shower, a private water closet with bidet, and refined finishes throughout. Two en-suite guest bedrooms with large custom-built closets open onto a private terrace with views of Sarasota Bay, ensuring comfort and privacy for family and guests alike. This rare beachfront residence combines luxury, privacy, and the ease of coastal living, all with breathtaking views and thoughtfully designed spaces for everyday enjoyment and elegant entertainment. Residents of La Firenza enjoy a boutique, gated setting with private beach access, a heated beachfront pool and spa, fitness facilities and secure garage parking.

3 Beds ⋅ 4 Baths ⋅ La Firenza SubDv. ⋅ 34228 Zip Code

Spectacular Gulf of Mexico views define this exceptional three-bedroom, three-and-a-half-bath residence that lives like a single-family home. A large wraparound terrace with a built-in grill offers seamless indoor-outdoor living, and private steps leading directly to the sandy beach – perfect for sunset entertaining or morning walks along the shore. Enter the home through a private elevator into a formal foyer with double door entry into the residence. The gracious living room is framed by expansive windows showcasing endless water views and exceptional sunsets flowing effortlessly to a built-in wet bar complete with wine refrigerator, ice maker, and a dedicated desk area—ideal for entertaining or casual work-from-home moments. A formal dining room with elegant ceiling detail makes hosting a dinner party a treat. Plantation shutters throughout the residence add a coastal and private touch. The gourmet kitchen is designed for both function and style, offering a large island for gathering, side-by-side Sub-Zero refrigerator and freezer, Wolf gas cooktop, Wolf oven with warming drawer, generous pantry, and a cozy desk area for browsing favorite recipes. A large center island and charming breakfast nook are the perfect spots for morning coffee or casual meals. Adjacent to the kitchen, the inviting keeping room opens to a private east-facing terrace with beautiful sunrise and views of Sarasota Bay. The expansive owner’s suite is a true retreat, featuring its own breakfast bar with sink and refrigerator for enjoying morning coffee while overlooking the Gulf. Two oversized, custom-built walk-in closets provide exceptional storage. The spa-inspired bath includes double vanities, a glass-enclosed shower, a private water closet with bidet, and refined finishes throughout. Two en-suite guest bedrooms with large custom-built closets open onto a private terrace with views of Sarasota Bay, ensuring comfort and privacy for family and guests alike. This rare beachfront residence combines luxury, privacy, and the ease of coastal living, all with breathtaking views and thoughtfully designed spaces for everyday enjoyment and elegant entertainment. Residents of La Firenza enjoy a boutique, gated setting with private beach access, a heated beachfront pool and spa, fitness facilities and secure garage parking.

4127 Gulf Of Mexico Drive Unit N102, Longboat Key

1000 Longboat Club Road Unit 403, Longboat Key

$949,000

Experience refined coastal living behind the gates of the Longboat Key Club at Privateer South — a serene waterfront retreat where the Gulf sets the rhythm of each day. This exclusive Longboat Key enclave blends timeless Old Florida charm with resort-style amenities. Residents enjoy access to the Longboat Key Club’s championship golf, tennis, deep-water marina, fine dining, and private beach club, while Privateer South offers intimate beachfront living in a 12-story tower at 1000 Longboat Club Road. This fourth-floor corner residence is a fully renovated two-bedroom, two-bath home that captures the essence of coastal elegance. Floor-to-ceiling windows and sliding glass doors open to wraparound balconies with eastern, southern, and partial Gulf views. Begin your mornings with sunrise over Sarasota Bay and the Intracoastal Waterway, as soft hues of pink and gold fill the open living and dining spaces. By afternoon, enjoy sweeping southern views of powder-white sand and turquoise Gulf waters, accompanied by the gentle sound of waves. The interior renovation reflects modern sophistication and comfort. A sleek galley kitchen with quartz countertops, stainless steel appliances, and custom cabinetry flows seamlessly into the bright living-dining area. Neutral tones, shiplap accents, and high-end finishes create an inviting, light-filled space ideal for entertaining or relaxing. The primary suite features desirable southern exposure and a refreshed en-suite bath with dual vanities and a walk-in shower. The second bedroom offers flexibility as a guest room, office, or private retreat, with the guest bath refreshed as well, in a clean, contemporary style. Daily living feels effortlessly indulgent. From the lobby, take the elevator to the heated Gulf-front pool and spa, complete with lounge seating overlooking the shoreline. Manicured pathways lead to private beach access, where dunes, complimentary chairs and umbrellas, and uncrowded sands create the perfect setting for sunset walks and frequent dolphin and pelican sightings. Residents also enjoy beachside grilling, on-site tennis, and the simple pleasures of Gulf coastal living. Gated security, covered parking, and the low-density South tower — with approximately 62 residences — provide both privacy and a welcoming community atmosphere shared by seasonal and full-time residents alike. Evenings on the balcony are unforgettable, with brilliant sunsets fading into star-filled skies over the Gulf. Inside, the open layout invites relaxed dinners, quiet reading, and peaceful nights accompanied by the sound of the water. This beautifully renovated corner residence offers the perfect balance of comfort, elegance, and breathtaking scenery in one of Florida’s most sought-after barrier island communities.

2 Beds ⋅ 2 Baths ⋅ Privateer South SubDv. ⋅ 34228 Zip Code

Experience refined coastal living behind the gates of the Longboat Key Club at Privateer South — a serene waterfront retreat where the Gulf sets the rhythm of each day. This exclusive Longboat Key enclave blends timeless Old Florida charm with resort-style amenities. Residents enjoy access to the Longboat Key Club’s championship golf, tennis, deep-water marina, fine dining, and private beach club, while Privateer South offers intimate beachfront living in a 12-story tower at 1000 Longboat Club Road. This fourth-floor corner residence is a fully renovated two-bedroom, two-bath home that captures the essence of coastal elegance. Floor-to-ceiling windows and sliding glass doors open to wraparound balconies with eastern, southern, and partial Gulf views. Begin your mornings with sunrise over Sarasota Bay and the Intracoastal Waterway, as soft hues of pink and gold fill the open living and dining spaces. By afternoon, enjoy sweeping southern views of powder-white sand and turquoise Gulf waters, accompanied by the gentle sound of waves. The interior renovation reflects modern sophistication and comfort. A sleek galley kitchen with quartz countertops, stainless steel appliances, and custom cabinetry flows seamlessly into the bright living-dining area. Neutral tones, shiplap accents, and high-end finishes create an inviting, light-filled space ideal for entertaining or relaxing. The primary suite features desirable southern exposure and a refreshed en-suite bath with dual vanities and a walk-in shower. The second bedroom offers flexibility as a guest room, office, or private retreat, with the guest bath refreshed as well, in a clean, contemporary style. Daily living feels effortlessly indulgent. From the lobby, take the elevator to the heated Gulf-front pool and spa, complete with lounge seating overlooking the shoreline. Manicured pathways lead to private beach access, where dunes, complimentary chairs and umbrellas, and uncrowded sands create the perfect setting for sunset walks and frequent dolphin and pelican sightings. Residents also enjoy beachside grilling, on-site tennis, and the simple pleasures of Gulf coastal living. Gated security, covered parking, and the low-density South tower — with approximately 62 residences — provide both privacy and a welcoming community atmosphere shared by seasonal and full-time residents alike. Evenings on the balcony are unforgettable, with brilliant sunsets fading into star-filled skies over the Gulf. Inside, the open layout invites relaxed dinners, quiet reading, and peaceful nights accompanied by the sound of the water. This beautifully renovated corner residence offers the perfect balance of comfort, elegance, and breathtaking scenery in one of Florida’s most sought-after barrier island communities.

1000 Longboat Club Road Unit 403, Longboat Key

2600 Harbourside Drive Unit J-09, Longboat Key

$380,000

Unique location on the lawn at Longboat Key Club Moorings! A 70 x 21 slip that is conveniently located near the Marina Village. One of the boaters favorite location. Club membership is required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 65 LOA; beam depends on the vessel. Call to discuss.

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

Unique location on the lawn at Longboat Key Club Moorings! A 70 x 21 slip that is conveniently located near the Marina Village. One of the boaters favorite location. Club membership is required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 65 LOA; beam depends on the vessel. Call to discuss.

2600 Harbourside Drive Unit J-09, Longboat Key

$529,000

Your easy island escape awaits in the beach-to-bay community of Sutton Place on Longboat Key. Spend your days at the deeded Gulf beach, lounging by one of two heated pools, kayaking on the bay, or heading out on the water—all within the community. This two-bedroom townhome is ideal for seasonal or year round living, offering impact windows and doors, steel roof trusses, and a private oversized garage for bikes, beach chairs, and island gear. The renovated kitchen features quartz countertops and Bosch appliances, and both bedrooms include walk-in closets and fully tiled baths. Unwind on two enclosed balconies overlooking a tranquil pond, then lock up and travel with confidence. Centrally located mid-island, Sutton Place offers the perfect blend of resort-style amenities in a beautiful setting.

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

Your easy island escape awaits in the beach-to-bay community of Sutton Place on Longboat Key. Spend your days at the deeded Gulf beach, lounging by one of two heated pools, kayaking on the bay, or heading out on the water—all within the community. This two-bedroom townhome is ideal for seasonal or year round living, offering impact windows and doors, steel roof trusses, and a private oversized garage for bikes, beach chairs, and island gear. The renovated kitchen features quartz countertops and Bosch appliances, and both bedrooms include walk-in closets and fully tiled baths. Unwind on two enclosed balconies overlooking a tranquil pond, then lock up and travel with confidence. Centrally located mid-island, Sutton Place offers the perfect blend of resort-style amenities in a beautiful setting.

531 Sutton Place, Longboat Key

$485,000

Sutton Place is perfectly situated on the tropical grounds of the Longboat Harbour Community. The two-bedroom, two-bathroom unit features beautiful views of the Sarasota Bay, spacious living area, full-size kitchen with stainless steel appliances and granite countertops, dining area and 3 flat-screen TV’s. If the amenities on the interior of the condo aren’t enough – the community of Sutton Place boasts two heated swimming pools, fishing pier and game room, complete with billiards and ping-pong; along with a fitness center and clubhouse. Deeded beach access is located directly across the street.

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

Sutton Place is perfectly situated on the tropical grounds of the Longboat Harbour Community. The two-bedroom, two-bathroom unit features beautiful views of the Sarasota Bay, spacious living area, full-size kitchen with stainless steel appliances and granite countertops, dining area and 3 flat-screen TV’s. If the amenities on the interior of the condo aren’t enough – the community of Sutton Place boasts two heated swimming pools, fishing pier and game room, complete with billiards and ping-pong; along with a fitness center and clubhouse. Deeded beach access is located directly across the street.

605 Sutton Place Unit 102, Longboat Key

2800 Harbourside Drive Unit E-12, Longboat Key

$300,000

Spacious E-dock! Slip E-12, a 60 ft x 21 ft. slip in the marina. Plenty of deep water and cool breezes. LBKC Membership is required. A 60 ft. x 21 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 55 LOA, usable beam is 19 ft at the head of the slip. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 55 LOA; beam depends on the vessel. Call to discuss!

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

Spacious E-dock! Slip E-12, a 60 ft x 21 ft. slip in the marina. Plenty of deep water and cool breezes. LBKC Membership is required. A 60 ft. x 21 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 55 LOA, usable beam is 19 ft at the head of the slip. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 55 LOA; beam depends on the vessel. Call to discuss!

2800 Harbourside Drive Unit E-12, Longboat Key

535 Sanctuary Drive Unit C807, Longboat Key

$3,500,000

Sanctuary penthouse with spectacular views of the Gulf, and Intracoastal Waterway to Sarasota. *NOW UNFURNISHED*. Total renovations completed in 2023 with nothing overlooked, including but not limited to EFCO turtle-approved glass, high-impact double pane hurricane sliders and windows, crystal custom kitchen cabinets by SRQ Custom Cabinetry, Thermador appliances including induction cooktop, wall-mounted microwave and convection oven, side-by-side Thermador refrigerator, Wi-Fi enabled dryer and hood fan, laundry room with added pantry features and a newly created breakfast bar. Complete water filtration system and quartz countertops throughout, with 5.5-inch baseboards with custom-milled crown molding and trim, solid wood doors, rectified 12-by-60-inch porcelain tile flooring, and custom built-ins in living room and primary bedroom. Hunter Douglas remote-controlled blinds, approximately 10-foot-high ceilings complete with skylights, tankless hot water system, and two zoned air conditioning units installed in 2019 and 2023. Amenities include cable, water and internet. New roof in 2024. Storage locker with under-building parking. Nearly 18 acres with 1,200 feet of Gulf of Mexico beachfront, an Olympic-sized heated pool and spa with extensive pool decks, a fire pit and gazebos to provide shade. A 24/7 guard gate, Har-Tru tennis courts, on-site management, and a two-story clubhouse come complete with a fitness center, showers, saunas and a large entertaining room with catering facilities. Membership to the Longboat Key Club is available which would include six restaurants, 45 holes of golf, 20 tennis courts plus other amenities. You are close to shopping, Publix, CVS, places of worship, a library, town hall and banks, St. Armands Circle along with Sarasota and all it offers.

3 Beds ⋅ 3 Baths ⋅ Sanctuary SubDv. ⋅ 34228 Zip Code

Sanctuary penthouse with spectacular views of the Gulf, and Intracoastal Waterway to Sarasota. *NOW UNFURNISHED*. Total renovations completed in 2023 with nothing overlooked, including but not limited to EFCO turtle-approved glass, high-impact double pane hurricane sliders and windows, crystal custom kitchen cabinets by SRQ Custom Cabinetry, Thermador appliances including induction cooktop, wall-mounted microwave and convection oven, side-by-side Thermador refrigerator, Wi-Fi enabled dryer and hood fan, laundry room with added pantry features and a newly created breakfast bar. Complete water filtration system and quartz countertops throughout, with 5.5-inch baseboards with custom-milled crown molding and trim, solid wood doors, rectified 12-by-60-inch porcelain tile flooring, and custom built-ins in living room and primary bedroom. Hunter Douglas remote-controlled blinds, approximately 10-foot-high ceilings complete with skylights, tankless hot water system, and two zoned air conditioning units installed in 2019 and 2023. Amenities include cable, water and internet. New roof in 2024. Storage locker with under-building parking. Nearly 18 acres with 1,200 feet of Gulf of Mexico beachfront, an Olympic-sized heated pool and spa with extensive pool decks, a fire pit and gazebos to provide shade. A 24/7 guard gate, Har-Tru tennis courts, on-site management, and a two-story clubhouse come complete with a fitness center, showers, saunas and a large entertaining room with catering facilities. Membership to the Longboat Key Club is available which would include six restaurants, 45 holes of golf, 20 tennis courts plus other amenities. You are close to shopping, Publix, CVS, places of worship, a library, town hall and banks, St. Armands Circle along with Sarasota and all it offers.

535 Sanctuary Drive Unit C807, Longboat Key

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