Refine Search
Map
Sort by
4500 Gulf Of Mexico Drive Unit 206, Longboat Key
$769,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
"One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!” This residence is now available for public and private showings. Restricted access resulted in only three private showings in six months. Buyer's have a rare chance to discover a home that’s been under the radar. (Do not let the days on the market fool you. Snowbirds were unable to view this listing the entire "season"). The only coveted South Marina corner/end unit currently on the market at Windward Bay—these special residences are truly prized. End units are usually the first to sell, and for good reason: they offer approximately 250 additional square feet of living space, flooding your home with light and delivering a bright, inviting atmosphere you’ll love. This second-floor location is equally exceptional—it’s the only level where you can enjoy continuous flooring throughout, creating a sleek and modern look. No one below means more freedom, more fun, and more style. Truly extraordinary, this special end unit offers a front-row seat to nature’s most enchanting show. Picture dolphins leaping in the sparkling waters and gentle manatees gliding just below your window—the very reason the current owners fell in love with this home. From breathtaking sunrises to moonlit reflections shimmering across Sarasota Bay, every moment feels like a postcard come to life. Step inside and feel the difference! Where luxury meets comfort with a complete remodel featuring a stunning Thomasville kitchen, sleek new floors, and beautifully updated bathrooms (2022). Enjoy modern conveniences like a Midea refrigerator, remote-control blinds (2025), and most importantly peace of mind with automatic hurricane shutters in the Living and Florida Rooms. This two-bedroom, two-bath property is more than a condo—it’s a lifestyle defined by serenity, security, spectacular views, and maintenance free living. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete, Monthly Condo Fees for 2025 were actually reduced, and the new 2026 Monthly Condo fees only increased by $13. Own the best of Longboat Key Bayfront living and make it yours before it’s just a memory! Paradise has an address..and it's 4500 Gulf of Mexico Drive #G206 on Longboat Key, in the rare gem of a community known as Windward Bay! Contact us today to schedule your private showing. Live the Magic & Don't Miss Out! Your Waterfront Dream Awaits!”

4500 Gulf Of Mexico Drive Unit 206, Longboat Key
510 Harbor Gate Way, Longboat Key
$3,950,000
4 Beds ⋅ 6 Baths ⋅ Bay Isles SubDv. ⋅ 34228 Zip Code
A Waterfront Work of Art. Experience a one-of-a-kind waterfront residence on Longboat Key — now offered at an exceptional new value. Designed around three interconnected circular "pods," the residence flows like a choreographed dance. There are no awkward hallways, no wasted corners, no spaces that feel like afterthoughts. Curved walls carry throughout every room — even into the garage — creating a cohesive design statement that's genuinely rare in residential construction at any price point. This architectural masterpiece is a sculptural composition of flowing living spaces connected by custom corridors, delivering remarkable privacy, abundant natural light, and seamless indoor–outdoor living. The dramatic Great Room pod showcases soaring wood-paneled ceilings and expansive walls of glass that frame tranquil water views. The circular primary suite is a private retreat featuring a spa-inspired bath with dual showers, a lounge area, private office, and direct access to the pool and spa terrace. At the heart of the home, the striking circular kitchen is both artful and functional, centered around a curved island beneath a two-story ceiling and skylight, with a thoughtfully designed radial appliance layout. Two en-suite guest bedrooms open to private patios, while the fully self-contained Secondary Primary Suite above the impressive 32' x 23' three-car garage offers independent HVAC, a luxury bath with steam shower and sauna, and flexible living space ideal for extended guests or multigenerational living. Outdoors, the property embraces the waterfront lifestyle with protected deep sailboat water, a private dock with a 12,000-pound lift, and a resort-style pool and spa designed for entertaining and relaxation. Located behind the 24-hour guarded gates of Bay Isles, residents also enjoy exclusive access to the Bay Isles Beach Club on the Gulf of Mexico.

510 Harbor Gate Way, Longboat Key
4380 Exeter Drive Unit H202, Longboat Key
$480,000
2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code
Live the best of Longboat Key from Longboat Harbour, a gated Bay-to-Beach community where boating, beach days, recreation, and waterfront relaxation are all part of everyday life. This beautifully updated, turnkey second-floor residence offers 2 bedrooms, 2 baths, peaceful water views, and an open floor plan designed for effortless coastal living. What truly sets Longboat Harbour apart is the lifestyle. Just a short walk across the street brings you to the community’s private deeded Gulf beach access, where residents enjoy a full beach house with bathrooms, showers, beach chair storage, and reserved parking. It is easy to grab your chair, head to the sand, take a swim in the Gulf, or settle in for one of Longboat Key’s unforgettable sunsets. For boating enthusiasts, the community’s deep-water marina offers sailboat access with no bridges to the bay, making it easy to enjoy Sarasota Bay and the surrounding waterways. Boat slips are available to residents on a first-come, first-served basis for a nominal fee, with water and electric service available at each slip. There is always something to enjoy at Longboat Harbour, with endless ways to embrace the island lifestyle without ever leaving the community. Residents can take advantage of four heated swimming pools, tennis and pickleball courts, a fitness center, sauna, shuffleboard, putting green, fishing pier, kayak storage and launch area, clubhouse, billiards, card room, library, art studio, woodworking shop, meeting spaces, picnic areas with grills, and beautifully maintained walking paths throughout the property. Beyond the amenities, Longboat Harbour offers a warm and welcoming social atmosphere with planned activities, resident events, and regular community updates, creating plenty of opportunities to connect with neighbors and enjoy the community. Inside the residence, the coastal setting continues with a bright, open living area that extends to an exceptionally spacious screened lanai. Sliding glass doors fill the space with natural light and frame peaceful water views, creating an inviting setting for morning coffee, outdoor dining, or simply relaxing and enjoying the surroundings. The condo was fully updated in 2025 with luxury vinyl plank flooring, refreshed ceilings, fresh paint, and a redesigned kitchen featuring white cabinetry, quartz countertops, a coastal glass backsplash, and a coffee bar. Both bathrooms have also been beautifully renovated with contemporary finishes, including porcelain tile, quartz vanities, and a frameless glass shower in the primary suite. Additional conveniences include a designated covered parking space, the private storage closet on the lanai, and an additional assigned personal storage conveniently located on the second floor near the residence. The monthly association fee includes hazard, hurricane, and flood insurance, and the community’s reserves are fully funded. Owners may also rent their unit up to twice per year, with a minimum lease term of one month, offering added flexibility for those who may wish to enjoy the residence seasonally. For those seeking more than just a residence, Longboat Harbour offers a true island lifestyle where beach, boating, recreation, waterfront living, and community all come together in one exceptional Longboat Key setting, and Unit H202 is the perfect place to enjoy it all with its turnkey interiors, peaceful water views, and beautifully updated coastal style.

4380 Exeter Drive Unit H202, Longboat Key
530 De Narvaez Drive, Longboat Key
$4,295,000
6 Beds ⋅ 6 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code
New Construction - Discover the epitome of waterfront luxury with this newly built home in the heart of Longboat Key—competitively priced and move-in ready. Nestled along a private canal, this 5-bedroom plus den, 4,106 sq ft residence blends contemporary sophistication with coastal appeal. Designed for effortless indoor-outdoor living, the home boasts two spacious lanais, a private pool and spa, and an elevated foundation at 9.5 feet for added peace of mind. Boaters will enjoy concrete canal bulkhead with quick access to the Gulf of Mexico, perfect for endless days on the water. Inside, the home features engineered hardwood flooring, sleek quartz countertops throughout, a large walk-in pantry, and the convenience of dual laundry rooms. Set in a tranquil, private location just minutes from Longboat Key’s renowned beaches, golf courses, and upscale dining, this home is a rare gem. Don’t miss your opportunity to own a waterfront retreat in one of Florida’s most sought-after coastal communities.

530 De Narvaez Drive, Longboat Key
757 Hideaway Bay Drive, Longboat Key
$6,295,000
4 Beds ⋅ 5 Baths ⋅ Hideaway Bay Subdivision SubDv. ⋅ 34228 Zip Code
Introducing Maison d’Azur, a custom waterfront estate in the prestigious Hideaway Bay enclave on the north end of Longboat Key. WHERE COASTAL LUXURY LIVING MEETS THE BAY! This exquisite four-bedroom, five-bath Key West-inspired residence, crafted by acclaimed builder John Cannon, seamlessly blends indoor and outdoor living to create an atmosphere of refined luxury reminiscent of a boutique hotel. Situated on over a quarter of an acre, this bayfront property commands breathtaking, unobstructed views. Enjoy the vibrant hues of sunrise and sunset over tranquil waters, with palm fronds swaying in the coastal breeze. With a newly renovated private forty-foot-deep water dock and boat lift, Maison d’Azur is a haven for boat enthusiasts and nature lovers. Spend afternoons in the saltwater pool and evenings on the loggia as the Belt of Venus rises over Sarasota Bay. Enjoy dining from your custom outdoor kitchen, surrounded by lush tropical landscaping. Step inside to experience luxury and meticulous craftsmanship, with a grand foyer featuring soaring ceilings and custom pillars. The open floor plan connects a chef’s kitchen, equipped with Sub Zero, Miele, Fisher and Paykel, and Wolf appliances, to a spacious family room with built in cabinetry, creating an inviting atmosphere for entertaining. Archways lead to elegantly decorated formal dining and living rooms. Ascend the private elevator to the second floor, where a great room with a custom entertainment center awaits, along with a study perfect for savoring a cognac on the captain’s porch. The expansive second floor offers a loggia and bedrooms with stunning panoramic views of the pool and Sarasota Bay. Maison d’Azur embodies exquisite taste and timeless beauty. With imported materials and innovative technology throughout, every detail has been curated for an elegant experience. This residence is sold fully furnished, with pieces selected to enhance each room’s design and ambiance. Hideaway Bay is located on Longboat Key, an eleven-mile island off the coast of Sarasota. This enclave of only seventeen estates is steps away from the deeded beach and boasts two private tennis courts. Residents enjoy easy access to premier country clubs, golf courses, waterfront activities, dining options, and upscale shopping. Experience coastal living where every day feels like a vacation amidst the beauty and tranquility of the Gulf Coast. This property sustained no damage from the storms/hurricanes of last year. It boasts an elevation of 10.5’, ensuring you stay high and dry.

757 Hideaway Bay Drive, Longboat Key
1591 Gulf Of Mexico Drive Unit 216, Longboat Key
$2,750,000
1 Beds ⋅ 2 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code
Incredible value at St. Regis Longboat Key. The last two one bedroom residences sold for $2,970,000 and $2,975,000. Step inside this spacious residence to discover a clean, modern interior with a sophisticated Palm Beach vibe. Designed for both style and comfort, this home features a gracious great room featuring floor-to-ceiling windows that flood the interiors with natural light and open to the large, 765 square foot private terrace with a built-in gas grill—perfect for gardening, entertaining friends and family, or relaxing outdoors. The chef’s kitchen is outfitted with Poggenpohl cabinetry, Wolf appliances, a Sub-Zero refrigerator, and Sub-Zero wine and beverage refrigerator, blending elegance with functionality. The owner’s suite also boasts floor-to-ceiling windows, a custom designed closet, and a luxurious bathroom with a frameless walk-in shower, Toto mechanized commode, and double vanities. With generous square footage and a thoughtful layout, this residence easily accommodates overnight guests while maintaining a sense of privacy. Additional features include electronic blinds throughout, adding both convenience and sophistication. Designer light fixtures add an elegant touch throughout the home. St. Regis Longboat Key offers a distinguished array of amenities meticulously curated for its residents. The Private Resident’s Clubhouse offers an environment of exclusivity, complemented by a state-of-the-art fitness center, as well as a pool and spa area reserved solely for residential use. Residents are granted privileged access to the legendary St. Regis Butler and Concierge services, which exemplify world-class hospitality and attention to detail. An extraordinary oceanfront spa awaits, alongside diverse dining experiences that showcase the highest standards of culinary excellence. Personal cabanas along the shore create private retreats for relaxation, while the family-friendly amenities include a meandering lazy river and a unique saltwater lagoon. This lagoon is home to a vibrant array of tropical fish species, graceful stingrays, and the resort’s resident tortoises, offering a captivating wildlife experience within the lush grounds. Spanning seventeen acres of beachfront on the coveted Longboat Key barrier island, this private oasis is conveniently located only 3.5 miles from St. Armand’s Circle, the region’s premier destination for shopping and dining. Whether seeking tranquil solitude or an active social environment, every aspect of life at St. Regis Longboat Key has been thoughtfully designed to anticipate and fulfill the desires of its residents. This offering represents more than just a residence; it is an invitation to embrace the legendary St. Regis lifestyle, defined by elegance, comfort, and outstanding service. Begin your journey to extraordinary Gulf side living.

1591 Gulf Of Mexico Drive Unit 216, Longboat Key
490 N Shore Road Unit 6, Longboat Key
$699,000
2 Beds ⋅ 3 Baths ⋅ Northgate Of Longboat Key SubDv. ⋅ 34228 Zip Code
This rare offering is all about the one-of-a-kind BREATHTAKING VIEWS overlooking multiple waterways across Greer island, towards the Intracoastal and out to the gorgeous Gulf of Mexico sunsets! Situated on the quiet north end of Longboat Key in a boutique waterfront, building containing only 9 townhouse style residences: this is island living at its best! It features two bedrooms and 2 and a half baths plus a bonus ground floor air conditioned room and a workshop. Take the steps up to your first living level and enjoy a galley kitchen open to the large great room with sliders to one of 2 outdoor balconies above the ground level, poolside covered porch. On this level is also a half bath. Take the steps up to the second level and the views become even more astounding through the sliders from the Primary ensuite bedroom! Here you will also find the 2nd bedroom and the second bath. Besides the sparkling waterside pool, this small and friendly community has 3 small docks available that allow for easy water access with your kayak, paddleboard or small boat. And don’t forget it has its own clay tennis court as well. One of the nicest and widest beaches on Longboat Key is located just down the street and it wraps all the way around Greer island where you can stand and admire your condo across the waterway from your walk! Multiple restaurants and shopping destinations are within a bike ride or short walk away and the cultural epicenter of downtown Sarasota and Bradenton are just off island when you choose to leave. This may well be the laid-back island life style you are searching for.

490 N Shore Road Unit 6, Longboat Key