Windward Bay Condos for Sale

Windward Bay Condos for Sale

Welcome to Windward Bay, a hidden gem nestled in the heart of Florida's stunning coastline. This enchanting subdivision offers a serene escape from the hustle and bustle of everyday life, making it the perfect place for those seeking relaxation and a vibrant community. Windward Bay is renowned for its picturesque landscapes, featuring lush greenery and breathtaking views of the tranquil waters, creating a picturesque backdrop for your new home.

Within this charming community, you will find an array of beautiful condos for sale, each designed with comfort and style in mind. These condos boast spacious layouts, modern amenities, and stunning balconies that invite you to unwind while soaking in the spectacular sunsets. Whether you’re looking for a cozy retreat or a spacious residence, Windward Bay has something to suit every lifestyle.

Residents of Windward Bay enjoy a wealth of amenities, including a sparkling community pool, well-maintained walking paths, and direct access to the pristine beaches that Florida is famous for. Additionally, the subdivision is conveniently located near shopping, dining, and recreational activities, ensuring that you have everything you need just a stone's throw away.

Imagine waking up each day in this idyllic paradise, where the sun shines bright and the ocean breeze whispers through the palm trees. If you’re ready to embrace a life of leisure and luxury, explore the condos for sale in Windward Bay today and discover your dream home in this enchanting Florida community. Your coastal paradise awaits!

Newest Windward Bay Condos for Sale

$825,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv.
Discover coastal living at its finest in this beautifully positioned 2-bedroom, 2-bath condominium on one of Longboat Key’s most sought-after stretches. This residence offers spectacular, breathtaking views from both private lanais—perfect for enjoying sunrise coffee or evening sunsets over the water. Inside, the layout is bright and inviting, with seamless indoor-outdoor flow that maximizes the scenery from multiple vantage points. Whether you’re looking for a full-time residence or a serene getaway, this condo delivers both comfort and location. The community is elevating its appeal with exciting enhancements, including upcoming clubhouse renovations featuring a boutique fitness center, newly refreshed landscaping, and a hot tub addition to the pool deck—creating a true resort-style atmosphere with two heated pools, beach cabanas, car wash station, a tennis and pickleball court, shuffleboard court, kayak rack, outdoor storage and a welcoming grilling convenience behind Club 72. This split plan FURNISHED 5th floor panoramic view, master en-suite unit awaits YOU! Enjoy the best of island living with pristine beaches, nearby dining, and a relaxed yet refined lifestyle—all just moments from your door. R&R IS THE PACE, LBK IS THE PLACE!!!!

4825 Gulf Of Mexico Drive Unit 504, Longboat Key
$364,000
3 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv.
Rarely available three-bedroom, two-bath first-floor end residence in the active, gated community of Tarpon Bay. This residence features tile flooring, a desirable split bedroom floor plan and an open, functional layout designed for comfortable living. A quiet screened lanai provides privacy and a relaxing outdoor setting surrounded by natural landscape. This pet-friendly community offers a full amenity package including Har-Tru lighted tennis courts, pickleball, basketball, bocce, a children's play area, lakefront gazebo, fishing, canoe and kayak storage, and scenic sidewalks for recreation or jogging. The community also features a clubhouse with fitness center, business center, resort-style infinity pool and spa, clubroom with catering kitchen, covered outdoor grilling area, card room and billiards room. Ideally located in North Naples, Tarpon Bay is close to shopping, dining, approximately 20 minutes to Vanderbilt Beach and RSW Airport.

1882 Tarpon Bay Drive S Unit 101, Naples
$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
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