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 delightful subdivision offers a perfect blend of tranquility and vibrant community living, making it an ideal destination for those seeking a serene yet active lifestyle. Windward Bay is renowned for its picturesque views, lush landscaping, and proximity to the sparkling waters of the Gulf of Mexico, providing residents with a true slice of paradise.

As you explore the condos for sale in Windward Bay, you’ll discover a variety of spacious floor plans designed to cater to every lifestyle. Whether you’re looking for a cozy retreat or a larger space to entertain family and friends, these condos offer modern amenities, tasteful finishes, and breathtaking views of the surrounding nature. Many units feature open-concept living areas, private balconies, and access to community pools and fitness centers, ensuring that every day feels like a vacation.

Beyond the condos, Windward Bay is conveniently located near a wealth of recreational opportunities. Spend your weekends basking on the nearby beaches, indulging in water sports, or exploring local shops and dining options. The community is also just a short drive away from vibrant downtown areas, offering a variety of cultural and entertainment options.

Experience the charm of Windward Bay, where coastal living meets community spirit. With its stunning condos for sale and a lifestyle that embraces the best of Florida living, this subdivision is truly a place you’ll love to call home. Don’t miss your chance to be part of this enchanting community—your dream condo awaits!

Newest Windward Bay Condos for Sale

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

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

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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Samantha Haringa

Samantha Haringa was born and raised in Massachusetts in the Greater Boston Area. Raised in a family of avid boaters and fisherman with the love for water, sand, and sunsets; moving to Cape Coral was a dream come true. Spending summers as a kid in Marco Island with her grandparents marked the beginning of the pursuit for the lifestyle and passions that the communities of SWFL have to offer. As a resident in the heart of SWFL in Cape Coral, Samantha is a part of the fabric of this vibrant and growing community of families and professionals that are all seeking that same love for the endless summers and treasured sunsets. Coming from a family of entrepreneurs and with twenty plus years of work in client management roles, Samantha has an innate and unrelenting passion for each client’s experience. It’s this passion that drove her to enter the Real Estate Industry. She recognized the singular importance of a client’s experience when buying, selling, or relocating to FL, and the need for a Realtor who would match the enthusiasm and expectations of their clients for this main life event. Plotting a course on the home ownership journey by listening, understanding, and appreciating the stated desires of each client is of paramount importance to her. Samantha’s authenticity, kindness and servant leadership provides every client with the experience of a Realtor whose moral compass remains anchored on the real estate needs and priorities of her clients.

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