Windward Bay Condos for Sale

Windward Bay Condos for Sale

Welcome to Windward Bay, a picturesque subdivision nestled along the serene shores of Florida's Gulf Coast. This charming community offers a perfect blend of coastal living and modern convenience, making it an ideal destination for those seeking a vibrant lifestyle in a tranquil setting.

Windward Bay is renowned for its stunning waterfront views, lush landscapes, and a plethora of amenities that cater to residents’ every need. The community features beautifully designed condos for sale that boast spacious layouts, contemporary finishes, and private balconies where you can bask in the warm Florida sun while enjoying breathtaking sunsets over the water. Each condo is thoughtfully crafted to provide a comfortable and stylish living experience, perfect for both year-round residents and seasonal visitors.

Living in Windward Bay means having access to a variety of recreational activities right at your doorstep. Spend your days lounging by the community pool, taking leisurely strolls along the waterfront, or indulging in water sports on the nearby beaches. For those who enjoy a more active lifestyle, the area offers numerous walking trails, golf courses, and parks.

In addition to its natural beauty, Windward Bay is conveniently located near shopping, dining, and entertainment options. With easy access to major highways, you can explore all that Florida has to offer, from vibrant cities to tranquil nature reserves.

If you’re searching for a slice of paradise in Florida, Windward Bay's condos for sale present an unparalleled opportunity to embrace a relaxed lifestyle in a stunning waterfront community. Come discover the charm of Windward Bay and make it your new home!

Newest Windward Bay Condos for Sale

$349,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv.
Set in one of North Naples’ most convenient locations, this beautiful home in Tarpon Bay offers a new roof, new exteriors, turnkey easy living, a private preserve view and an entire community that has just undergone a complete coastal refresh. Inside, you will find new kitchen appliances, new light coastal flooring, a new air-conditioning system, a new water heater, a new washer and dryer, and the rare convenience of natural gas. Large windows fill the home with natural light while overlooking the quiet preserve, creating a bright, relaxed coastal atmosphere. Elevator service provides easy community access. The entire Tarpon Bay community has recently been refreshed with brand-new roofs as well, beautifully updated building exteriors and a renewed coastal aesthetic throughout. Directly across the private, quiet street is the Castaways Club, the centerpiece of Tarpon Bay’s resort-style lifestyle, with an infinity-edge pool overlooking a massive lake, a spa, a full fitness center, pickleball and clay tennis courts, grilling areas, professional on-site management, a boat dock and a kayak launch. Beautiful lakes, fountains, mature palms, paver roundabouts and an impressive illuminated entrance create a peaceful, polished setting. Just minutes from Interstate 75 and approximately 15 minutes from Mercato, Naples beaches, shopping and dining, with Southwest Florida International Airport just under 30 minutes away. This is an exceptional opportunity to enjoy a fully updated residence in a beautifully located North Naples community with low-maintenance living.

1886 Tarpon Bay Drive S Unit 204, Naples
$799,999
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv.
Welcome to your Longboat Key PENTHOUSE, where unobstructed PANORAMIC WATER VIEWS from every room create a breathtaking backdrop from the moment you walk through the door. Recently renovated from top to bottom and offered TURNKEY FURNISHED, this residence is ready to enjoy from day one. The BRAND-NEW KITCHEN showcases quartz countertops, custom cabinetry, and all-new stainless-steel appliances, opening seamlessly to the bright and airy living space. Both bathrooms have been completely updated with modern finishes and quartz countertops, creating a fresh, cohesive feel throughout the home. Other thoughtful updates throughout include luxury vinyl flooring throughout, fresh carpeting in the bedrooms, beautifully remodeled, IMPACT WINDOWS, generous storage, and the convenience of an in-unit washer and dryer. Located in the pet-friendly waterfront community of Windward Bay, residents enjoy an impressive collection of amenities including boat slips, two swimming pools, a fitness center, sauna, tennis and pickleball courts, and three beach access points. NO upcoming special assessments, FULLY FUNDED reserves, and a PASSED Milestone. Perfectly positioned on Longboat Key, this penthouse offers the relaxed island lifestyle while keeping you conveniently connected to the dining, shopping, beaches, and entertainment of Longboat Key, St Armands, and Anna Maria Island. Whether you're searching for a full-time residence or your own Florida getaway, this turnkey waterfront penthouse is ready to welcome you home.

4800 Gulf Of Mexico Drive Unit PH 3, Longboat Key
$725,000
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.
This residence is now available for public and private showings. "One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!” 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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