Windward Bay Homes with Bay/Harbor Frontage

Windward Bay Homes with Bay/Harbor Frontage

Welcome to Windward Bay, a picturesque subdivision nestled in the heart of Longboat Key, Florida, within the charming Manatee County. This idyllic community offers a unique blend of coastal living and luxurious comfort, making it a sought-after destination for those seeking a serene lifestyle by the water.

Windward Bay is renowned for its stunning homes with breathtaking bay and harbor frontage. Imagine waking up each morning to the gentle sounds of lapping waves and the sight of sailboats gliding across the shimmering waters. Each residence within this exclusive subdivision boasts a unique architectural charm, with many featuring expansive windows that invite natural light and provide panoramic views of the surrounding beauty.

The community is perfect for boating enthusiasts, as residents enjoy direct access to the bay and nearby Gulf of Mexico. Whether you’re an avid fisherman or simply enjoy leisurely cruises, Windward Bay is your gateway to endless aquatic adventures. The lush landscaping and meticulously maintained grounds create a tranquil environment, perfect for relaxing or entertaining guests.

In addition to its natural beauty, Windward Bay offers proximity to some of Florida's finest dining, shopping, and cultural experiences. Explore the vibrant local scene, or take a short drive to nearby Sarasota for a taste of the arts and entertainment.

Experience the ultimate in waterfront living at Windward Bay, where luxury meets nature in a harmonious embrace. Your dream home awaits in this coastal paradise!

Newest Windward Bay Homes with Bay/Harbor 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!” 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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