Windward Bay Homes with Intracoastal Waterway Frontage

Windward Bay Homes with Intracoastal Waterway Frontage

Welcome to Windward Bay, a hidden gem nestled in the picturesque Longboat Key, Florida. This exclusive subdivision offers a unique blend of luxurious living and natural beauty, making it the perfect haven for those seeking tranquility and elegance by the water.

Windward Bay is renowned for its stunning homes that boast breathtaking views of the Intracoastal Waterway. Imagine waking up each morning to the gentle sound of waves lapping against the shore and the sight of boats gliding by—this is the everyday reality for residents of this exceptional community. Each home is thoughtfully designed, featuring spacious layouts, modern amenities, and expansive outdoor areas perfect for entertaining or simply soaking in the Florida sunshine.

The allure of Windward Bay extends beyond its captivating homes. Residents enjoy access to a variety of community amenities, including well-maintained walking paths, lush landscaping, and private docks for those who love boating or fishing. With the Intracoastal Waterway at your doorstep, adventure awaits just outside your door, whether it’s a leisurely day on the water or a sunset cruise with friends and family.

Located in the charming city of Longboat Key, Windward Bay offers a serene lifestyle while being just a short drive away from vibrant local shops, fine dining, and the stunning beaches that Florida is famous for. Experience the perfect blend of luxury and leisure in Windward Bay—where your dream home awaits along the tranquil shores of the Intracoastal Waterway.

Newest Windward Bay Homes with Intracoastal Waterway Frontage

$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

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