Windward Bay Homes with Trees/Woods View

Windward Bay Homes with Trees/Woods View

Welcome to Windward Bay, a hidden gem nestled in the picturesque Longboat Key, Florida. This charming subdivision is a perfect blend of coastal elegance and natural beauty, offering residents a serene lifestyle surrounded by lush greenery and breathtaking water views.

Windward Bay boasts a unique selection of homes that provide stunning views of the trees and woods, allowing you to immerse yourself in the tranquility of nature right from your backyard. Imagine waking up each morning to the gentle rustle of leaves and the soothing sounds of birdsong, creating a peaceful oasis that feels like a private retreat.

The community is thoughtfully designed to enhance your living experience, with spacious homes that feature modern amenities and open floor plans. Each residence is strategically positioned to maximize the picturesque views, ensuring that you can enjoy the beauty of the outdoors from the comfort of your home.

Windward Bay is not just a place to live; it's a lifestyle. Residents can enjoy the nearby pristine beaches, where sun-soaked days and stunning sunsets await. The area is also home to a variety of dining, shopping, and recreational options, making it easy to indulge in the vibrant culture of Longboat Key.

Whether you are looking for a year-round residence or a seasonal getaway, Windward Bay offers a unique opportunity to experience the best of Florida living. With its enchanting views and friendly community atmosphere, this subdivision is the perfect place to call home. Come and discover the charm of Windward Bay, where nature and luxury seamlessly intertwine.

Newest Windward Bay Homes with Trees/Woods View

$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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