Windward Bay Homes with Bay View Water Frontage

Windward Bay Homes with Bay View Water Frontage

Welcome to Windward Bay, a hidden gem nestled in the picturesque Longboat Key, Florida. This exclusive subdivision offers a unique blend of luxury living and serene coastal charm, making it a coveted destination for those seeking a slice of paradise.

Windward Bay is renowned for its stunning homes that boast breathtaking bay view waterfrontage. Imagine waking up each morning to the gentle lapping of waves and the soft glow of the sun rising over the water. These exquisite residences are designed to maximize the stunning natural surroundings, featuring expansive windows and spacious decks that invite the outdoors in. Whether you’re sipping your morning coffee or hosting a sunset gathering with friends, the views here are nothing short of spectacular.

The community itself is thoughtfully designed to foster a sense of belonging and tranquility. With lush landscaping, pristine walking paths, and access to private docks, residents can enjoy a lifestyle filled with outdoor activities. From kayaking in the bay to leisurely strolls along the shoreline, Windward Bay embraces the essence of coastal living.

Located just moments away from the vibrant culture of Longboat Key, residents can indulge in fine dining, boutique shopping, and world-class golf. Plus, the stunning beaches of the Gulf Coast are just a stone's throw away, providing endless opportunities for relaxation and recreation.

In Windward Bay, you’ll find more than just a home; you’ll discover a lifestyle that celebrates the beauty of nature and the joy of community. Come experience the magic of waterfront living in this idyllic Florida paradise!

Newest Windward Bay Homes with Bay View Water Frontage

$769,000
2 Beds 2 Baths Windward Bay SubDv.
"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

Start Your Search