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$999,000

Coastal Living Perfected on Longboat Key Discover the ultimate island retreat at 726 Jungle Queen Way, a beautifully reimagined 2-bedroom, 2-bath waterfront home where modern comfort meets timeless Florida charm. Tucked away on a peaceful canal just steps from the Gulf of Mexico, this residence offers the rare privilege of deeded beach access, 125ft canal frontage, and a resort-style saltwater pool - everything you need to live each day like a vacation. Wake up to soft morning light glistening off the water and ease into your day with coffee poolside, surrounded by lush tropical landscaping and the hush of palm fronds swaying in the breeze. Launch your boat from the private dock pilings on the deep-water canal and explore Sarasota Bay or head out toward Egmont Key. After a day on the water, rinse off in the outdoor shower, slip into the saltwater pool, or unwind on the travertine deck beneath wide island skies that glow at sunset. Evenings invite laid-back luxury - cocktails by the firepit, good company, and a canopy of stars overhead. Inside, this home blends classic coastal character with thoughtful, high-end updates throughout. The light-filled living spaces feel open yet intimate, with plantation shutters, fresh neutral tones, new baseboards and trim that anchors the living room with style. The redesigned kitchen shines with quartz countertops, stainless-steel appliances, and sleek cabinetry, while both bathrooms echo a spa-inspired sensibility with crisp, elegant finishes. The family room’s canal views beyond the French doors provide a quiet reminder that you’re always connected to the water. Recent updates lend peace of mind with new HVAC (2019), refreshed interior paint, new interior doors, and professional flood mitigation - including new drywall and rewired electrical. The exterior is equally turnkey, with manicured landscaping, a paver driveway, and a shaded carport for convenience. Living on Longboat Key means embracing an effortless, elegant coastal lifestyle. From here, you’re minutes to St. Armands Circle, Anna Maria Island, and downtown Sarasota, with boutique shopping, fine dining, dog-friendly parks, and beach paths all within easy reach. Boat in the morning. Beach at sunset. Poolside under the stars. This is more than a home - it’s the Longboat Key lifestyle realized.

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

Coastal Living Perfected on Longboat Key Discover the ultimate island retreat at 726 Jungle Queen Way, a beautifully reimagined 2-bedroom, 2-bath waterfront home where modern comfort meets timeless Florida charm. Tucked away on a peaceful canal just steps from the Gulf of Mexico, this residence offers the rare privilege of deeded beach access, 125ft canal frontage, and a resort-style saltwater pool - everything you need to live each day like a vacation. Wake up to soft morning light glistening off the water and ease into your day with coffee poolside, surrounded by lush tropical landscaping and the hush of palm fronds swaying in the breeze. Launch your boat from the private dock pilings on the deep-water canal and explore Sarasota Bay or head out toward Egmont Key. After a day on the water, rinse off in the outdoor shower, slip into the saltwater pool, or unwind on the travertine deck beneath wide island skies that glow at sunset. Evenings invite laid-back luxury - cocktails by the firepit, good company, and a canopy of stars overhead. Inside, this home blends classic coastal character with thoughtful, high-end updates throughout. The light-filled living spaces feel open yet intimate, with plantation shutters, fresh neutral tones, new baseboards and trim that anchors the living room with style. The redesigned kitchen shines with quartz countertops, stainless-steel appliances, and sleek cabinetry, while both bathrooms echo a spa-inspired sensibility with crisp, elegant finishes. The family room’s canal views beyond the French doors provide a quiet reminder that you’re always connected to the water. Recent updates lend peace of mind with new HVAC (2019), refreshed interior paint, new interior doors, and professional flood mitigation - including new drywall and rewired electrical. The exterior is equally turnkey, with manicured landscaping, a paver driveway, and a shaded carport for convenience. Living on Longboat Key means embracing an effortless, elegant coastal lifestyle. From here, you’re minutes to St. Armands Circle, Anna Maria Island, and downtown Sarasota, with boutique shopping, fine dining, dog-friendly parks, and beach paths all within easy reach. Boat in the morning. Beach at sunset. Poolside under the stars. This is more than a home - it’s the Longboat Key lifestyle realized.

726 Jungle Queen Way, Longboat Key

$5,749,000

Introducing the newest custom residence by Brista Homes, where exceptional craftsmanship and thoughtful design come together in a limited and highly refined offering. Nestled along a quiet canal in the sought-after waterfront community of Country Club Shores, this 4216 square-foot residence captures the essence of the Longboat Key boating lifestyle. With desirable south-facing rear exposure, tranquil canal views create a peaceful backdrop to daily living, while upper balconies frame beautiful views of Sarasota Bay. The home’s architecture, floor plan, and interior selections were curated by Brista’s in-house design team, drawing on years of experience building on Longboat Key and a deep understanding of what today’s waterfront buyers value most—timeless architecture, premium materials, and seamless indoor-outdoor living. A handcrafted iron pivot entry door framed by natural stone detailing creates a striking first impression. Inside, pocketing glass doors open the main living spaces to a resort-style outdoor setting where a custom salt water pool and elevated heated spa are surrounded by porcelain pavers and lush coastal landscaping. A fully equipped outdoor kitchen creates the ideal setting for entertaining along the water. At the heart of the home, the kitchen blends refined design with exceptional functionality. Custom Italian cabinetry is complemented by a dramatic Quartzite waterfall island and matching hood feature. A premium appliance suite by Miele — including a built-in refrigerator, integrated dishwashers, speed oven, and built in coffee maker — is complemented with a striking 48-inch dual-fuel range. A hidden butler’s pantry and custom wine display add both style and practicality for effortless entertaining. The great room centers around a sleek linear fireplace, creating a sophisticated gathering space. Upstairs, a spacious club room with a media wall and wet bar offers a relaxed setting for evenings with family and guests. Architectural details throughout the home include white oak plank flooring, a dramatic floating staircase, recessed baseboards, and clean modern lines that reflect a refined coastal aesthetic. Modern conveniences include whole-home audio, a whole house generator, multi-zone climate control, and integrated security. Located within one of Longboat Key’s most desirable boating communities, where deepwater canals provide quick access to Sarasota Bay and the Gulf of Mexico, this newly completed custom residence represents a rare opportunity to experience waterfront living defined by thoughtful design, exceptional craftsmanship, and enduring quality.

5 Beds ⋅ 7 Baths ⋅ Country Club Shores SubDv. ⋅ 34228 Zip Code

Introducing the newest custom residence by Brista Homes, where exceptional craftsmanship and thoughtful design come together in a limited and highly refined offering. Nestled along a quiet canal in the sought-after waterfront community of Country Club Shores, this 4216 square-foot residence captures the essence of the Longboat Key boating lifestyle. With desirable south-facing rear exposure, tranquil canal views create a peaceful backdrop to daily living, while upper balconies frame beautiful views of Sarasota Bay. The home’s architecture, floor plan, and interior selections were curated by Brista’s in-house design team, drawing on years of experience building on Longboat Key and a deep understanding of what today’s waterfront buyers value most—timeless architecture, premium materials, and seamless indoor-outdoor living. A handcrafted iron pivot entry door framed by natural stone detailing creates a striking first impression. Inside, pocketing glass doors open the main living spaces to a resort-style outdoor setting where a custom salt water pool and elevated heated spa are surrounded by porcelain pavers and lush coastal landscaping. A fully equipped outdoor kitchen creates the ideal setting for entertaining along the water. At the heart of the home, the kitchen blends refined design with exceptional functionality. Custom Italian cabinetry is complemented by a dramatic Quartzite waterfall island and matching hood feature. A premium appliance suite by Miele — including a built-in refrigerator, integrated dishwashers, speed oven, and built in coffee maker — is complemented with a striking 48-inch dual-fuel range. A hidden butler’s pantry and custom wine display add both style and practicality for effortless entertaining. The great room centers around a sleek linear fireplace, creating a sophisticated gathering space. Upstairs, a spacious club room with a media wall and wet bar offers a relaxed setting for evenings with family and guests. Architectural details throughout the home include white oak plank flooring, a dramatic floating staircase, recessed baseboards, and clean modern lines that reflect a refined coastal aesthetic. Modern conveniences include whole-home audio, a whole house generator, multi-zone climate control, and integrated security. Located within one of Longboat Key’s most desirable boating communities, where deepwater canals provide quick access to Sarasota Bay and the Gulf of Mexico, this newly completed custom residence represents a rare opportunity to experience waterfront living defined by thoughtful design, exceptional craftsmanship, and enduring quality.

530 Chipping Lane, 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

Welcome to Your Beach House Sanctuary on Longboat Key! Experience the ultimate coastal lifestyle in this beautifully renovated island retreat, ideally situated just four homes from Tarawitt Point on a deep-water canal. Set on an expansive 125x90 ft lot, this waterfront property offers 125 feet of seawall with dockage for a boat up to 30 feet, a jet ski lift, and additional space for all your water toys. With the Intracoastal Waterway just 50 yards from the canal’s end, you’ll enjoy direct, no-bridge access to Sarasota Bay—perfect for fishing, cruising, or sunset boating. Catch bait and be fishing in under 30 minutes! Inside, this meticulously maintained home features: 3 spacious bedrooms, 2 full baths + 1 half bath, 1-car garage, Open-concept floor plan with stunning bay views! The oversized primary suite offers a comfortable seating area, TV space, a generous walk-in closet, and a beautifully updated bath with dual vanities and a large walk-in shower. The kitchen and living area flow seamlessly onto a porch overlooking the bay—ideal for morning coffee or evening cocktails. Renovated in 2022, the home boasts a new roof, new windows and doors, granite countertops, new appliances, updated bathrooms, new flooring, fresh interior and exterior paint, and even a relaxing hot tub. Deeded beach access sits directly across Tarawitt Drive, offering effortless enjoyment of the Gulf’s turquoise waters and sugar-sand beaches. Enjoy walkable access to some of the island’s favorite dining destinations, including: Harry's Restaurant, Euphemia Haye, The Lazy Lobster, A short bike ride takes you to: The Shore Restaurant, Mar Vista Dockside Restaurant And you’re just an easy drive to Anna Maria Island, St. Armands Circle, and downtown Sarasota. This is more than a home—it’s a waterfront lifestyle defined by boating, beach days, and breathtaking bay views.

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

Welcome to Your Beach House Sanctuary on Longboat Key! Experience the ultimate coastal lifestyle in this beautifully renovated island retreat, ideally situated just four homes from Tarawitt Point on a deep-water canal. Set on an expansive 125x90 ft lot, this waterfront property offers 125 feet of seawall with dockage for a boat up to 30 feet, a jet ski lift, and additional space for all your water toys. With the Intracoastal Waterway just 50 yards from the canal’s end, you’ll enjoy direct, no-bridge access to Sarasota Bay—perfect for fishing, cruising, or sunset boating. Catch bait and be fishing in under 30 minutes! Inside, this meticulously maintained home features: 3 spacious bedrooms, 2 full baths + 1 half bath, 1-car garage, Open-concept floor plan with stunning bay views! The oversized primary suite offers a comfortable seating area, TV space, a generous walk-in closet, and a beautifully updated bath with dual vanities and a large walk-in shower. The kitchen and living area flow seamlessly onto a porch overlooking the bay—ideal for morning coffee or evening cocktails. Renovated in 2022, the home boasts a new roof, new windows and doors, granite countertops, new appliances, updated bathrooms, new flooring, fresh interior and exterior paint, and even a relaxing hot tub. Deeded beach access sits directly across Tarawitt Drive, offering effortless enjoyment of the Gulf’s turquoise waters and sugar-sand beaches. Enjoy walkable access to some of the island’s favorite dining destinations, including: Harry's Restaurant, Euphemia Haye, The Lazy Lobster, A short bike ride takes you to: The Shore Restaurant, Mar Vista Dockside Restaurant And you’re just an easy drive to Anna Maria Island, St. Armands Circle, and downtown Sarasota. This is more than a home—it’s a waterfront lifestyle defined by boating, beach days, and breathtaking bay views.

825 Tarawitt Drive, Longboat Key

$2,995,000

PRICE IMPROVEMENT! In the tranquil north end of Longboat Key, where Gulf breezes drift through the palms and the pace slows to a whisper, this extraordinary beach retreat captures the essence of refined coastal living. Positioned on nearly half an acre of canal front property and encompassing over 3,000 square feet of interior living space (more than 6,000 square feet total), the residence sits just across from the ultra convenient public beach access. This unique residence offers the rare luxury of both boating and beachside lifestyles in one remarkable setting. Recently transformed through a stunning renovation and offered turnkey furnished, the five bedroom, three bath waterfront home showcases long, picturesque canal views and an effortless indoor outdoor flow. A NEW ROOF in 2023 and new impact windows were installed in 2022 provide peace of mind. Vaulted ceilings and light-filled spaces that feel both expansive and inviting. At the heart of the home, the chef’s kitchen blends timeless style with modern performance, featuring classic shaker cabinetry, gleaming white quartz countertops, high-end white Café appliances, and generous island seating ideal for gathering. The primary suite is a private sanctuary of nearly 700 square feet, complete with dual walk-in closets and a spa-inspired bath designed for indulgence, including a dramatic double soaking tub with jets, fireplace and TV, a Moen technology-enhanced shower, and electronic Woodbridge toilets that elevate daily living with comfort and innovation. Each of the guest bedrooms offer sizeable walk in closets. Step from the screened lanai off the living room down to a resort-caliber outdoor environment that rivals the finest destinations, where a heated pool and spa anchor the space alongside a putting green, waterfront fire pit, game area, and a beautifully pavered outdoor kitchen designed for effortless entertaining. For boating enthusiasts, the property is exceptionally equipped with a 10,000-pound boat lift and a second dock for added enjoyment. Substantial non-conforming enhanced storage beneath the home and a spacious three-car garage provide versatility without compromising luxury, making this a rare waterfront compound where mornings begin at the beach, afternoons unfold on the water, and evenings are spent poolside under the stars. Located a short distance to the Bridge Street Pier which offers ample dining, shopping and entertainment options, this residence truly is the ultimate beach getaway.

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

PRICE IMPROVEMENT! In the tranquil north end of Longboat Key, where Gulf breezes drift through the palms and the pace slows to a whisper, this extraordinary beach retreat captures the essence of refined coastal living. Positioned on nearly half an acre of canal front property and encompassing over 3,000 square feet of interior living space (more than 6,000 square feet total), the residence sits just across from the ultra convenient public beach access. This unique residence offers the rare luxury of both boating and beachside lifestyles in one remarkable setting. Recently transformed through a stunning renovation and offered turnkey furnished, the five bedroom, three bath waterfront home showcases long, picturesque canal views and an effortless indoor outdoor flow. A NEW ROOF in 2023 and new impact windows were installed in 2022 provide peace of mind. Vaulted ceilings and light-filled spaces that feel both expansive and inviting. At the heart of the home, the chef’s kitchen blends timeless style with modern performance, featuring classic shaker cabinetry, gleaming white quartz countertops, high-end white Café appliances, and generous island seating ideal for gathering. The primary suite is a private sanctuary of nearly 700 square feet, complete with dual walk-in closets and a spa-inspired bath designed for indulgence, including a dramatic double soaking tub with jets, fireplace and TV, a Moen technology-enhanced shower, and electronic Woodbridge toilets that elevate daily living with comfort and innovation. Each of the guest bedrooms offer sizeable walk in closets. Step from the screened lanai off the living room down to a resort-caliber outdoor environment that rivals the finest destinations, where a heated pool and spa anchor the space alongside a putting green, waterfront fire pit, game area, and a beautifully pavered outdoor kitchen designed for effortless entertaining. For boating enthusiasts, the property is exceptionally equipped with a 10,000-pound boat lift and a second dock for added enjoyment. Substantial non-conforming enhanced storage beneath the home and a spacious three-car garage provide versatility without compromising luxury, making this a rare waterfront compound where mornings begin at the beach, afternoons unfold on the water, and evenings are spent poolside under the stars. Located a short distance to the Bridge Street Pier which offers ample dining, shopping and entertainment options, this residence truly is the ultimate beach getaway.

501 Norton Street, 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

$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

$649,000

Welcome to Longboat Harbour, a gated waterfront community offering resort-style living on beautiful Longboat Key. This first-floor corner unit, N-106, features two bedrooms, two baths, and an assigned covered carport — all set against unparalleled views of Sarasota Bay and the Intracoastal Waterway. Step inside to find ceramis plank flooring throughout and a light-filled, open layout designed to maximize both comfort and scenery. The bright kitchen offers a convenient pass-through to the dining area and living room, allowing you to stay connected with guests while preparing meals. The spacious living room is lined with windows facing the water, delivering breathtaking sunrise views each morning. Sliding glass doors from both bedrooms open to a tiled three-season lanai, complete with additional sliders that lead directly to the outdoors — perfect for embracing Florida’s coastal lifestyle. Both bathrooms feature elegant granite countertops for durability and easy maintenance. ?? Exceptional Community Amenities Include: Private Beach Club with Parking, Four heated pools, Tennis and pickel balls courts, Fitness center, Clubhouse, On-ste manager and boat docks. (Available on a first come basis for sail or power boats) Whether you’re seeking a full-time residence, seasonal retreat, or investment opportunity, this waterfront gem offers the perfect blend of luxury, comfort, and active coastal living.

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

Welcome to Longboat Harbour, a gated waterfront community offering resort-style living on beautiful Longboat Key. This first-floor corner unit, N-106, features two bedrooms, two baths, and an assigned covered carport — all set against unparalleled views of Sarasota Bay and the Intracoastal Waterway. Step inside to find ceramis plank flooring throughout and a light-filled, open layout designed to maximize both comfort and scenery. The bright kitchen offers a convenient pass-through to the dining area and living room, allowing you to stay connected with guests while preparing meals. The spacious living room is lined with windows facing the water, delivering breathtaking sunrise views each morning. Sliding glass doors from both bedrooms open to a tiled three-season lanai, complete with additional sliders that lead directly to the outdoors — perfect for embracing Florida’s coastal lifestyle. Both bathrooms feature elegant granite countertops for durability and easy maintenance. ?? Exceptional Community Amenities Include: Private Beach Club with Parking, Four heated pools, Tennis and pickel balls courts, Fitness center, Clubhouse, On-ste manager and boat docks. (Available on a first come basis for sail or power boats) Whether you’re seeking a full-time residence, seasonal retreat, or investment opportunity, this waterfront gem offers the perfect blend of luxury, comfort, and active coastal living.

4440 Exeter Drive Unit 106, 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

$949,000

Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger. Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances. Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops. Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets. Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard. Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association. Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armand’s and Downtown Sarasota.

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

Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger. Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances. Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops. Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets. Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard. Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association. Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armand’s and Downtown Sarasota.

3435 Winding Oaks Drive Unit 18, 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

$659,000

Welcome to the Atrium—one of Longboat Key's most exceptional waterfront addresses. Perfectly positioned along the sparkling waters of Sarasota Bay, this stunning three-bedroom residence offers breathtaking panoramic views that will captivate you from sunrise to sunset. The spacious chef's kitchen is designed for both function and style, featuring abundant cabinetry, stainless steel appliances, and a double oven for the culinary enthusiast. Imagine preparing meals while gazing out at the endless blue waters of the bay—a view that never grows old. The thoughtfully designed split-bedroom floor plan provides privacy and comfort for family and guests. The expansive primary suite is a true retreat, surrounded by sliding glass doors that fill the room with natural light, welcome refreshing bay breezes, and provide direct access to the terrace where spectacular waterfront views await. This is coastal living at its finest. Ownership includes exclusive membership to the Bay Isles Beach Club, offering deeded beach access, social activities, scenic walking trails, heated pools, a state-of-the-art fitness center, tennis and pickleball courts, clubhouse amenities, and convenient kayak launches. For those seeking an even more elevated resort experience, optional membership to the Longboat Key Club provides access to championship golf, world-class Har-Tru tennis courts, a luxurious spa, waterfront dining, and a deep-water marina. Perfectly situated just minutes from St. Armand's Circle and downtown Sarasota's vibrant arts, shopping, and dining districts. Location, location, location is number one in Real Estate and this unit gets the award.

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

Welcome to the Atrium—one of Longboat Key's most exceptional waterfront addresses. Perfectly positioned along the sparkling waters of Sarasota Bay, this stunning three-bedroom residence offers breathtaking panoramic views that will captivate you from sunrise to sunset. The spacious chef's kitchen is designed for both function and style, featuring abundant cabinetry, stainless steel appliances, and a double oven for the culinary enthusiast. Imagine preparing meals while gazing out at the endless blue waters of the bay—a view that never grows old. The thoughtfully designed split-bedroom floor plan provides privacy and comfort for family and guests. The expansive primary suite is a true retreat, surrounded by sliding glass doors that fill the room with natural light, welcome refreshing bay breezes, and provide direct access to the terrace where spectacular waterfront views await. This is coastal living at its finest. Ownership includes exclusive membership to the Bay Isles Beach Club, offering deeded beach access, social activities, scenic walking trails, heated pools, a state-of-the-art fitness center, tennis and pickleball courts, clubhouse amenities, and convenient kayak launches. For those seeking an even more elevated resort experience, optional membership to the Longboat Key Club provides access to championship golf, world-class Har-Tru tennis courts, a luxurious spa, waterfront dining, and a deep-water marina. Perfectly situated just minutes from St. Armand's Circle and downtown Sarasota's vibrant arts, shopping, and dining districts. Location, location, location is number one in Real Estate and this unit gets the award.

2110 Harbourside Drive Unit 523, Longboat Key

$1,295,000

One or more photo(s) has been virtually staged. 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. 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

$1,650,000

Wrapped in lush, mature landscaping and set along a tranquil mangrove-lined canal, this waterfront 3BR/2.5BA residence on Longboat Key offers space, privacy and an inviting canvas for future vision. A circular paver driveway and stepped front entry create a gracious arrival, framed by tropical greenery and a classic barrel tile roof. Inside, cathedral ceilings with exposed beams, clerestory windows and a wall of glass sliders fill the great room with natural light. A corner fireplace adds warmth and character, while the open layout feels airy and welcoming. Sliders extend the living space outdoors to a wood deck shaded by a pergola, where peaceful canal views set a calming backdrop for everyday living. The kitchen brings a distinctive mid-century influence, featuring low-profile black-and-white cabinetry, a center island with sink, black stone countertops, white appliances, a breakfast bar, an eat-in area and an adjacent dining space that flows easily into the great room. It is functional and full of personality, with room to reimagine if desired. The primary suite is spacious, offering slider access to the deck and a large bath with dual vanities, spa tub and walk-in shower, presenting an opportunity to update and personalize. Guest bedrooms are comfortably sized, and the guest bath is generous with dual vanities. An in-residence laundry room adds convenience. Outdoors, a caged pool with spa sits privately to the side of the home, while the rear of the property opens to excellent boating water. A private dock and boat lift are positioned along a protected canal, bordered by mangroves and just moments from Sarasota Bay. Located in The Bayou, an intimate gated enclave within Bay Isles, residents enjoy access to the private Bay Isles Beach Club, along with optional membership to the Longboat Key Golf & Tennis Country Club and Harbourside Moorings deepwater slips. This is a rare opportunity to enjoy waterfront living today, with the freedom to shape what comes next in one of Longboat Key’s most desirable communities.

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

Wrapped in lush, mature landscaping and set along a tranquil mangrove-lined canal, this waterfront 3BR/2.5BA residence on Longboat Key offers space, privacy and an inviting canvas for future vision. A circular paver driveway and stepped front entry create a gracious arrival, framed by tropical greenery and a classic barrel tile roof. Inside, cathedral ceilings with exposed beams, clerestory windows and a wall of glass sliders fill the great room with natural light. A corner fireplace adds warmth and character, while the open layout feels airy and welcoming. Sliders extend the living space outdoors to a wood deck shaded by a pergola, where peaceful canal views set a calming backdrop for everyday living. The kitchen brings a distinctive mid-century influence, featuring low-profile black-and-white cabinetry, a center island with sink, black stone countertops, white appliances, a breakfast bar, an eat-in area and an adjacent dining space that flows easily into the great room. It is functional and full of personality, with room to reimagine if desired. The primary suite is spacious, offering slider access to the deck and a large bath with dual vanities, spa tub and walk-in shower, presenting an opportunity to update and personalize. Guest bedrooms are comfortably sized, and the guest bath is generous with dual vanities. An in-residence laundry room adds convenience. Outdoors, a caged pool with spa sits privately to the side of the home, while the rear of the property opens to excellent boating water. A private dock and boat lift are positioned along a protected canal, bordered by mangroves and just moments from Sarasota Bay. Located in The Bayou, an intimate gated enclave within Bay Isles, residents enjoy access to the private Bay Isles Beach Club, along with optional membership to the Longboat Key Golf & Tennis Country Club and Harbourside Moorings deepwater slips. This is a rare opportunity to enjoy waterfront living today, with the freedom to shape what comes next in one of Longboat Key’s most desirable communities.

3131 Bayou Sound, Longboat Key

$599,000

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

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

$1,049,000

Virtually Staged. 2BD+DEN! Positioned as the southern-most community on Longboat Keys’ Gulf of Mexico Drive is the stunning Tangerine Bay. Its presence of pristinely manicured tropical color admired by all that enter the Key. Within this gated community lies #515- horizontal to Sarasota’s bayfront experiencing views that span across blue waters abundant with active sea-life. This 2bd/Den/2.5bath/2-car private garage home, with excellent wall space for displaying your finest art collection, extends over 2,300 square feet of living space. Courtyard entry, equipped with gas hook-up for your own grill, offers slider access into the kitchen/ family room area which is perfect for a different entertaining perspective since the courtyard is large enough to also accommodate table and chairs. Of course, the coveted place to dwell will be the grand living/ dining area and balcony to experience morning sun over the calming waters or the miracle of all the hues the sky can offer as the sun begins to set behind you. Large primary en-suite enjoys the water view and slider access to the balcony, considerably sized walk-in closet and super-spacious bathroom to create the spa-like atmosphere of your dreams. #515 will not disappoint with the generous kitchen, kitchen water filtration, split floorplan, updated windows and doors, 2024 remote roll-down hurricane shutters, 2023 A/C, 2026 water heater, roof and sprinkler heads replaced approx. three years ago. With a spanning lap pool, meandering lush lounging areas, spa, fishing/day dock, tennis/ pickleball, fitness center and clubhouse- Tangerine Bay is poised for pleasure to all who get to call it home. For a small annual fee, owners can also become members of the Bay Isles Beach Club.

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

Virtually Staged. 2BD+DEN! Positioned as the southern-most community on Longboat Keys’ Gulf of Mexico Drive is the stunning Tangerine Bay. Its presence of pristinely manicured tropical color admired by all that enter the Key. Within this gated community lies #515- horizontal to Sarasota’s bayfront experiencing views that span across blue waters abundant with active sea-life. This 2bd/Den/2.5bath/2-car private garage home, with excellent wall space for displaying your finest art collection, extends over 2,300 square feet of living space. Courtyard entry, equipped with gas hook-up for your own grill, offers slider access into the kitchen/ family room area which is perfect for a different entertaining perspective since the courtyard is large enough to also accommodate table and chairs. Of course, the coveted place to dwell will be the grand living/ dining area and balcony to experience morning sun over the calming waters or the miracle of all the hues the sky can offer as the sun begins to set behind you. Large primary en-suite enjoys the water view and slider access to the balcony, considerably sized walk-in closet and super-spacious bathroom to create the spa-like atmosphere of your dreams. #515 will not disappoint with the generous kitchen, kitchen water filtration, split floorplan, updated windows and doors, 2024 remote roll-down hurricane shutters, 2023 A/C, 2026 water heater, roof and sprinkler heads replaced approx. three years ago. With a spanning lap pool, meandering lush lounging areas, spa, fishing/day dock, tennis/ pickleball, fitness center and clubhouse- Tangerine Bay is poised for pleasure to all who get to call it home. For a small annual fee, owners can also become members of the Bay Isles Beach Club.

380 Gulf Of Mexico Drive Unit 515, Longboat Key

$615,000

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

$1,100,000

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

$2,795,000

Set at the peaceful end of a wide, deep canal on the north end of Longboat Key, this waterfront residence in Emerald Harbor offers a rare combination of space, privacy and effortless boating access. With long views straight down the canal and quick entry to Sarasota Bay, the setting feels calm, open and ideally positioned for life on the water. A circular paver brick drive framed by meticulously maintained landscaping leads to the front entrance, where a barrel tile roof and timeless exterior details create a welcoming first impression. Inside, 3,098+/- sq. ft. of thoughtfully planned living space unfolds in soft neutral tones, complemented by abundant natural light, large tile flooring, crown molding and expansive windows throughout the main living areas. The living room is designed for seamless indoor-outdoor living, featuring a full wall of pocket sliders that open completely to a covered sitting area accented by a pecky cypress ceiling. From here, the view extends across the pool, private dock and calm canal beyond, creating a natural backdrop for both entertaining and everyday enjoyment. The kitchen anchors the home with ease and functionality, offering a center island with breakfast bar, wood cabinetry, stone countertops, stainless steel appliances, tile backsplash and pendant lighting. Its placement allows the home to flow comfortably for gatherings or quiet evenings alike. The floor plan offers exceptional flexibility, with two generously sized suites. The main primary suite features a tray ceiling, a large custom walk-in closet and a beautifully updated bath with dual vanities, glass-enclosed shower and convenient access to the outdoor living area. A second suite includes its own custom walk-in closet and en suite bath, making it ideal for guests or extended family. Two additional bedrooms and a study overlooking the water complete the layout, along with three and a half total baths. Outdoors, the setting feels private yet expansive, with a sparkling pool and a private dock equipped with a boat lift. The canal offers excellent boating water with no-bridge access to the Intracoastal Waterway, Sarasota Bay and the Gulf. Emerald Harbor is a bayside enclave of just 82 homes, known for its broad lagoon-style canals and deeded private beach access located one block away.

4 Beds ⋅ 4 Baths ⋅ Emerald Harbor SubDv. ⋅ 34228 Zip Code

Set at the peaceful end of a wide, deep canal on the north end of Longboat Key, this waterfront residence in Emerald Harbor offers a rare combination of space, privacy and effortless boating access. With long views straight down the canal and quick entry to Sarasota Bay, the setting feels calm, open and ideally positioned for life on the water. A circular paver brick drive framed by meticulously maintained landscaping leads to the front entrance, where a barrel tile roof and timeless exterior details create a welcoming first impression. Inside, 3,098+/- sq. ft. of thoughtfully planned living space unfolds in soft neutral tones, complemented by abundant natural light, large tile flooring, crown molding and expansive windows throughout the main living areas. The living room is designed for seamless indoor-outdoor living, featuring a full wall of pocket sliders that open completely to a covered sitting area accented by a pecky cypress ceiling. From here, the view extends across the pool, private dock and calm canal beyond, creating a natural backdrop for both entertaining and everyday enjoyment. The kitchen anchors the home with ease and functionality, offering a center island with breakfast bar, wood cabinetry, stone countertops, stainless steel appliances, tile backsplash and pendant lighting. Its placement allows the home to flow comfortably for gatherings or quiet evenings alike. The floor plan offers exceptional flexibility, with two generously sized suites. The main primary suite features a tray ceiling, a large custom walk-in closet and a beautifully updated bath with dual vanities, glass-enclosed shower and convenient access to the outdoor living area. A second suite includes its own custom walk-in closet and en suite bath, making it ideal for guests or extended family. Two additional bedrooms and a study overlooking the water complete the layout, along with three and a half total baths. Outdoors, the setting feels private yet expansive, with a sparkling pool and a private dock equipped with a boat lift. The canal offers excellent boating water with no-bridge access to the Intracoastal Waterway, Sarasota Bay and the Gulf. Emerald Harbor is a bayside enclave of just 82 homes, known for its broad lagoon-style canals and deeded private beach access located one block away.

5970 Emerald Harbor Drive, Longboat Key

$2,695,000

Experience the timeless appeal of a quintessential Florida island home, immersed in a lush tropical waterfront setting on Longboat Key. Elevated above a serene natural bayou off Sarasota Bay, this distinctive residence embodies the relaxed elegance of island living, with soaring ceilings, expansive wraparound decks, and pristine Gulf beaches just moments away. Launch a kayak from your private dock, enjoy exceptional fishing and bird-watching from your backyard, or keep your boat in one of the community's deepwater slips on the open bay. The association offers slips up to 43 feet in length, and either your private dock on the bayou or a bayfront slip may accommodate an optional boat lift. The spacious elevated residence is anchored by a dramatic great room featuring vaulted cedar ceilings and exposed beams. An expansive sunroom with a bar area and handcrafted display shelving, a dedicated library, an inviting family room, and a private office with extensive built-in cabinetry contribute to the home's distinctive character. The entire main living area is thoughtfully arranged on a single level. Extensive decking welcomes you at the front entry and wraps around a lush central atrium courtyard, creating exceptional spaces for outdoor dining, entertaining, and relaxation. A shaded cabana-inspired retreat offers comfort throughout the day, while the setting is equally suited for the addition of an elevated outdoor spa. The kitchen, centered around a generous island, is perfectly positioned for gathering with family and friends. The primary suite features a wall of windows overlooking the tranquil bayou, dual walk-in closets, and an additional wall of custom closet storage. A desirable split floor plan creates a private guest wing with two additional bedrooms and baths. Each guest room enjoys direct access to the surrounding decks and views of the tropical atrium. Two garages accommodate up to four vehicles and provide ample space for boats, golf carts, paddleboards, and additional storage. Most furnishings are included. Within Land's End, an intimate gated enclave of just 12 residences, owners enjoy maintenance-free landscaping, a heated swimming pool, tennis and pickleball courts, and beautifully landscaped grounds nestled among mature trees for exceptional privacy and convenient bay access. From here, a short walk or golf cart ride leads to the Gulf beach and popular island dining destinations, including Shore Longboat Key, Mar Vista Dockside Restaurant, and Whitney's. Nearby waterfront cafés, boutique shopping, fitness facilities, and a Pilates studio further enhance the island lifestyle. Enjoy breathtaking Gulf sunsets and tranquil bay sunrises from this exceptional waterfront community. Rarely does a property so perfectly capture the spirit of Old Florida, where tropical beauty, boating, nature, and beachside living come together in one of Longboat Key's most treasured island enclaves.

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

Experience the timeless appeal of a quintessential Florida island home, immersed in a lush tropical waterfront setting on Longboat Key. Elevated above a serene natural bayou off Sarasota Bay, this distinctive residence embodies the relaxed elegance of island living, with soaring ceilings, expansive wraparound decks, and pristine Gulf beaches just moments away. Launch a kayak from your private dock, enjoy exceptional fishing and bird-watching from your backyard, or keep your boat in one of the community's deepwater slips on the open bay. The association offers slips up to 43 feet in length, and either your private dock on the bayou or a bayfront slip may accommodate an optional boat lift. The spacious elevated residence is anchored by a dramatic great room featuring vaulted cedar ceilings and exposed beams. An expansive sunroom with a bar area and handcrafted display shelving, a dedicated library, an inviting family room, and a private office with extensive built-in cabinetry contribute to the home's distinctive character. The entire main living area is thoughtfully arranged on a single level. Extensive decking welcomes you at the front entry and wraps around a lush central atrium courtyard, creating exceptional spaces for outdoor dining, entertaining, and relaxation. A shaded cabana-inspired retreat offers comfort throughout the day, while the setting is equally suited for the addition of an elevated outdoor spa. The kitchen, centered around a generous island, is perfectly positioned for gathering with family and friends. The primary suite features a wall of windows overlooking the tranquil bayou, dual walk-in closets, and an additional wall of custom closet storage. A desirable split floor plan creates a private guest wing with two additional bedrooms and baths. Each guest room enjoys direct access to the surrounding decks and views of the tropical atrium. Two garages accommodate up to four vehicles and provide ample space for boats, golf carts, paddleboards, and additional storage. Most furnishings are included. Within Land's End, an intimate gated enclave of just 12 residences, owners enjoy maintenance-free landscaping, a heated swimming pool, tennis and pickleball courts, and beautifully landscaped grounds nestled among mature trees for exceptional privacy and convenient bay access. From here, a short walk or golf cart ride leads to the Gulf beach and popular island dining destinations, including Shore Longboat Key, Mar Vista Dockside Restaurant, and Whitney's. Nearby waterfront cafés, boutique shopping, fitness facilities, and a Pilates studio further enhance the island lifestyle. Enjoy breathtaking Gulf sunsets and tranquil bay sunrises from this exceptional waterfront community. Rarely does a property so perfectly capture the spirit of Old Florida, where tropical beauty, boating, nature, and beachside living come together in one of Longboat Key's most treasured island enclaves.

677 Lands End Drive, 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

$13,499,000

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

$695,000

Wow, New Unbelievable Price! Just Dropped. Now is your opportunity! New unbelievable price on this fully renovated and turn-key furnished Village of Longboat Key Home. Take Advantage Today. Brand new Roof, New Hurricane glass throughout, Full interior renovation with new furnishings, Block home on a Beautiful private lot with outdoor living space and room for a Pool, steps away from white sand and turquoise water. Rentability: the seller averages $55,000 a year in gross rental income while still enjoying personal use. Buy this property at an unbelievable price, rent it when you're not using it, and enjoy it for decades to come. Longboat Key's Coveted Village is on the exclusive North Tip of Longboat Key and this property is in the Heart of the Village. This is more than a home; it's the ultimate island lifestyle, delivered. Just a short, serene stroll separates you from the pristine beach and the island's best waterside dining. This property has been meticulously and fully remodeled, representing a rare "move-in ready" opportunity where every detail has been elevated. From top to bottom, inside and out, virtually nothing has been untouched. Open Concept: Step into an airy, open-plan great room, anchored by a brand-new kitchen - perfect for hosting or unwinding after a day on the water. Chef's Delight: The remodeled kitchen is a masterpiece featuring stunning marble countertops, custom cabinetry, all-new luxury appliances (including a mini wine refrigerator), and a chic island/bar. High-End Finishes: Enjoy the cohesive flow of new luxury vinyl plank flooring throughout every room, complemented by fresh, designer-selected interior paint. Peace of Mind: Recently installed, all new windows and sliding glass doors are Miami-Dade impact resistant, offering superior protection and efficiency. Also a brand new architectural three-tab shingle roof was just installed. Your Private Island Retreat: Spa-Inspired Baths: Both the master and second bathrooms have been fully renovated with stone shower flooring, elegant new tiles, and updated fixtures. Outdoor Oasis: New impact-resistant glass door opens to a spacious, private backyard. The highlight is the expansive, screened-in porch that wraps around the back of the house, overlooking a charming outdoor fire pit and grilling area. Beach Ready: An exterior shower and dedicated storage for your gear make rinsing off after a day at the beach effortless. The Village Lifestyle: To know The Village is to fall in love with it's relaxed, yet refined rhythm. This community places everything you desire at your fingertips: secluded walking trails, Bay access, community docks, waterfront dining, bars, gyms, shopping and the island's best beach access. The Village is one of the few places on Longboat Key where the golf cart isn't just legal, it's the preferred, fun, and convenient way to live. Bring the Kids, Friends, Pets, Boats and toys; with no HOA and packed full with desired island luxuries this is true island paradise. Come and see it today!

4 Beds ⋅ 2 Baths ⋅ Long Beach SubDv. ⋅ 34228 Zip Code

Wow, New Unbelievable Price! Just Dropped. Now is your opportunity! New unbelievable price on this fully renovated and turn-key furnished Village of Longboat Key Home. Take Advantage Today. Brand new Roof, New Hurricane glass throughout, Full interior renovation with new furnishings, Block home on a Beautiful private lot with outdoor living space and room for a Pool, steps away from white sand and turquoise water. Rentability: the seller averages $55,000 a year in gross rental income while still enjoying personal use. Buy this property at an unbelievable price, rent it when you're not using it, and enjoy it for decades to come. Longboat Key's Coveted Village is on the exclusive North Tip of Longboat Key and this property is in the Heart of the Village. This is more than a home; it's the ultimate island lifestyle, delivered. Just a short, serene stroll separates you from the pristine beach and the island's best waterside dining. This property has been meticulously and fully remodeled, representing a rare "move-in ready" opportunity where every detail has been elevated. From top to bottom, inside and out, virtually nothing has been untouched. Open Concept: Step into an airy, open-plan great room, anchored by a brand-new kitchen - perfect for hosting or unwinding after a day on the water. Chef's Delight: The remodeled kitchen is a masterpiece featuring stunning marble countertops, custom cabinetry, all-new luxury appliances (including a mini wine refrigerator), and a chic island/bar. High-End Finishes: Enjoy the cohesive flow of new luxury vinyl plank flooring throughout every room, complemented by fresh, designer-selected interior paint. Peace of Mind: Recently installed, all new windows and sliding glass doors are Miami-Dade impact resistant, offering superior protection and efficiency. Also a brand new architectural three-tab shingle roof was just installed. Your Private Island Retreat: Spa-Inspired Baths: Both the master and second bathrooms have been fully renovated with stone shower flooring, elegant new tiles, and updated fixtures. Outdoor Oasis: New impact-resistant glass door opens to a spacious, private backyard. The highlight is the expansive, screened-in porch that wraps around the back of the house, overlooking a charming outdoor fire pit and grilling area. Beach Ready: An exterior shower and dedicated storage for your gear make rinsing off after a day at the beach effortless. The Village Lifestyle: To know The Village is to fall in love with it's relaxed, yet refined rhythm. This community places everything you desire at your fingertips: secluded walking trails, Bay access, community docks, waterfront dining, bars, gyms, shopping and the island's best beach access. The Village is one of the few places on Longboat Key where the golf cart isn't just legal, it's the preferred, fun, and convenient way to live. Bring the Kids, Friends, Pets, Boats and toys; with no HOA and packed full with desired island luxuries this is true island paradise. Come and see it today!

690 Fox Street, 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

$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

$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

$22,000,000

Named the House of Columns by world-renowned, award-winning architect Carl Abbott, this palatial Bayfront estate stands as a singular expression of architectural distinction and craftsmanship. Encompassing close to five acres on the north end of Longboat Key spanning Sarasota Bay, the combined offering of 6610 and 6630 Gulf of Mexico Drive represents one of the most significant residential holdings available in the area, a legacy estate where endless views of sea and sky create an unforgettable backdrop for living. The property unfolds like a private peninsula, offering exceptional width, depth and privacy. On the eastern shoreline, calm bay waters reflect the morning light with open water, protected shoreline and bridgeless access to the Gulf of Mexico. The primary residence is gracefully positioned on the bayfront, designed to capture eastern exposure and long, tranquil water views across Sarasota Bay. Clean architectural lines, soaring interior volumes, and walls of glass create a continuous dialogue between interior and exterior. Ceilings soar up to 21 feet, allowing light to move freely throughout the home while maintaining warmth and livability. The elevator provides access across levels, while Lutron lighting and automated shades on every window and door allow the home to respond intuitively to the changing light of day. The residence has been impeccably maintained by its original owner, reflecting a level of care and stewardship rarely found. Infrastructure has been thoughtfully addressed, including a whole-home generator that ensures continuity and peace of mind. The owner’s garage sits under a cantilever with access to the interior elevator and an additional air-conditioned four-car garage with large workspace offers a total space for 6 cars and exceptional flexibility for collectors, hobbies or future customization. A lagoon-style pool sits within the landscape, offering a resort-like atmosphere while preserving privacy and water views. A private dock with two boat lifts provides immediate access to Sarasota Bay and the Intracoastal Waterway, creating a seamless boating lifestyle that complements the estate’s waterfrontage. The inclusion of 6630 Gulf of Mexico Drive allows owners to construct a guest house or secondary structure, offering flexibility for multigenerational living, guests, or staff accommodations, offering extraordinary future optionality and ensures the next owner retains control over one of Longboat Key’s irreplaceable resources, land. What ultimately distinguishes this offering is its irreplaceability. Estates of this size, with this combination of architectural pedigree, boating infrastructure, development flexibility and maintained condition are no longer being created. Despite its scale and seclusion, you are moments from the refined lifestyle Longboat Key is known for, private clubs, championship golf, fine dining, IMG Academy and the cultural offerings of Anna Maria Island, St. Armands Circle and downtown Sarasota just beyond the bridge. This is not merely a waterfront home, it is a generational legacy, unmatched in design, scale, privacy and location.

4 Beds ⋅ 7 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code

Named the House of Columns by world-renowned, award-winning architect Carl Abbott, this palatial Bayfront estate stands as a singular expression of architectural distinction and craftsmanship. Encompassing close to five acres on the north end of Longboat Key spanning Sarasota Bay, the combined offering of 6610 and 6630 Gulf of Mexico Drive represents one of the most significant residential holdings available in the area, a legacy estate where endless views of sea and sky create an unforgettable backdrop for living. The property unfolds like a private peninsula, offering exceptional width, depth and privacy. On the eastern shoreline, calm bay waters reflect the morning light with open water, protected shoreline and bridgeless access to the Gulf of Mexico. The primary residence is gracefully positioned on the bayfront, designed to capture eastern exposure and long, tranquil water views across Sarasota Bay. Clean architectural lines, soaring interior volumes, and walls of glass create a continuous dialogue between interior and exterior. Ceilings soar up to 21 feet, allowing light to move freely throughout the home while maintaining warmth and livability. The elevator provides access across levels, while Lutron lighting and automated shades on every window and door allow the home to respond intuitively to the changing light of day. The residence has been impeccably maintained by its original owner, reflecting a level of care and stewardship rarely found. Infrastructure has been thoughtfully addressed, including a whole-home generator that ensures continuity and peace of mind. The owner’s garage sits under a cantilever with access to the interior elevator and an additional air-conditioned four-car garage with large workspace offers a total space for 6 cars and exceptional flexibility for collectors, hobbies or future customization. A lagoon-style pool sits within the landscape, offering a resort-like atmosphere while preserving privacy and water views. A private dock with two boat lifts provides immediate access to Sarasota Bay and the Intracoastal Waterway, creating a seamless boating lifestyle that complements the estate’s waterfrontage. The inclusion of 6630 Gulf of Mexico Drive allows owners to construct a guest house or secondary structure, offering flexibility for multigenerational living, guests, or staff accommodations, offering extraordinary future optionality and ensures the next owner retains control over one of Longboat Key’s irreplaceable resources, land. What ultimately distinguishes this offering is its irreplaceability. Estates of this size, with this combination of architectural pedigree, boating infrastructure, development flexibility and maintained condition are no longer being created. Despite its scale and seclusion, you are moments from the refined lifestyle Longboat Key is known for, private clubs, championship golf, fine dining, IMG Academy and the cultural offerings of Anna Maria Island, St. Armands Circle and downtown Sarasota just beyond the bridge. This is not merely a waterfront home, it is a generational legacy, unmatched in design, scale, privacy and location.

6610 Gulf Of Mexico Drive, 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

$2,100,000

$100,000 PRICE REDUCTION—NOW OFFERED AT $2,100,000! Exceptional Longboat Key waterfront living just THREE HOMES FROM SARASOTA BAY. This completely renovated 3-bedroom, 2-bath canal-front home offers 1,853 sq. ft. of air-conditioned living space and 2,461 total sq. ft., combining an outstanding boating location with extensive recent improvements. Boaters will appreciate the newer seawall, 16,000-lb boat lift and 18' x 16' Trex dock with lighting and water, offering views toward Sarasota Bay and quick access to open water. Enjoy your private Pebble Tec pool and paver pool deck, both updated in 2024. Major improvements include a NEW FLAT TILE ROOF (2025), Carrier A/C (2024), A.O. Smith water heater, NuCORE waterproof flooring and plantation shutters throughout. The updated kitchen features Silestone quartz countertops, stainless-steel sink, Bosch 3-door refrigerator/freezer and dishwasher, plus stainless-steel GE range and microwave. The spacious living room features vaulted ceilings and recessed lighting, complemented by a separate dining room. The primary suite offers a walk-in closet with built-ins and an ensuite bath with dual sinks, large tiled shower, whirlpool tub and private water closet. A split-bedroom floor plan provides privacy for guests, with walk-in closets and an office area incorporated into the third bedroom. With major renovations completed, a private pool, exceptional boating amenities and a premier location just three homes from Sarasota Bay, 548 Gunwale Lane offers an outstanding opportunity to enjoy the Longboat Key waterfront lifestyle. NOW OFFERED AT $2,100,000!

3 Beds ⋅ 2 Baths ⋅ Country Club Shores SubDv. ⋅ 34228 Zip Code

$100,000 PRICE REDUCTION—NOW OFFERED AT $2,100,000! Exceptional Longboat Key waterfront living just THREE HOMES FROM SARASOTA BAY. This completely renovated 3-bedroom, 2-bath canal-front home offers 1,853 sq. ft. of air-conditioned living space and 2,461 total sq. ft., combining an outstanding boating location with extensive recent improvements. Boaters will appreciate the newer seawall, 16,000-lb boat lift and 18' x 16' Trex dock with lighting and water, offering views toward Sarasota Bay and quick access to open water. Enjoy your private Pebble Tec pool and paver pool deck, both updated in 2024. Major improvements include a NEW FLAT TILE ROOF (2025), Carrier A/C (2024), A.O. Smith water heater, NuCORE waterproof flooring and plantation shutters throughout. The updated kitchen features Silestone quartz countertops, stainless-steel sink, Bosch 3-door refrigerator/freezer and dishwasher, plus stainless-steel GE range and microwave. The spacious living room features vaulted ceilings and recessed lighting, complemented by a separate dining room. The primary suite offers a walk-in closet with built-ins and an ensuite bath with dual sinks, large tiled shower, whirlpool tub and private water closet. A split-bedroom floor plan provides privacy for guests, with walk-in closets and an office area incorporated into the third bedroom. With major renovations completed, a private pool, exceptional boating amenities and a premier location just three homes from Sarasota Bay, 548 Gunwale Lane offers an outstanding opportunity to enjoy the Longboat Key waterfront lifestyle. NOW OFFERED AT $2,100,000!

548 Gunwale Lane, Longboat Key