Windward Bay Real Estate

Windward Bay Real Estate

Welcome to Windward Bay, a picturesque subdivision nestled along the stunning shores of Florida’s Gulf Coast. This charming community perfectly blends coastal living with modern conveniences, making it an ideal haven for families, retirees, and everyone in between.

Windward Bay boasts a variety of beautifully designed homes, each exuding a unique character while maintaining the coastal aesthetic that defines the area. From spacious single-family residences to cozy townhomes, there’s a perfect fit for everyone looking to embrace the Florida lifestyle. Many properties feature breathtaking views of the bay, private docks, and lush landscaping, inviting you to enjoy the outdoors right from your backyard.

The community is not just about beautiful homes; it's about a vibrant lifestyle. Residents of Windward Bay enjoy access to a host of amenities, including a sparkling community pool, well-maintained walking trails, and picnic areas that encourage outdoor gatherings. The nearby beaches offer endless opportunities for sunbathing, swimming, and water sports, while local parks provide spaces for family outings and recreational activities.

Conveniently located, Windward Bay is just a short drive from a variety of shopping, dining, and entertainment options. Whether you’re indulging in fresh seafood at a local restaurant or exploring boutique shops, you’ll find everything you need within reach.

With its serene atmosphere, friendly neighbors, and stunning natural beauty, Windward Bay offers a truly exceptional quality of life. Come and discover your dream home in this enchanting Florida community—where every day feels like a vacation!

Newest Listings in Windward Bay

4 Beds ⋅ 3 Baths ⋅ Windward Bay SubDv.

NO CDD Fees here folks! Welcome to Windwater, a gated community in the heart of Parrish. This stunning Mesa Verde offers 2,601 square feet of thoughtfully designed living space, a 3-car garage, and quality upgrades that set it apart from new construction. From the moment you step inside, you'll appreciate the spacious open-concept layout, double tray ceiling with crown molding, an abundance of natural light, and the beautiful luxury vinyl plank flooring. The well-designed split floor plan offers the perfect balance of privacy and functionality, making it ideal for families, guests, or those working from home. Speaking of guests, one guest bedroom has a private full bath! One of the home's standout features is the oversized screened lanai, complete with upgraded paver flooring that stretches across the entire rear of the home. Whether you're hosting friends, enjoying your morning coffee, or simply taking in the Florida lifestyle, this expansive outdoor living space is sure to impress. Freshly installed landscaping extends across the backyard offering privacy. Windwater residents enjoy resort-style amenities including a community pool, playground, and sidewalks, all while being just minutes from I-75, Fort Hamer Road, shopping, dining, top-rated schools, and everything Parrish has to offer.

12351 51st Street E, Parrish

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.

Welcome to coastal luxury living in Windward Bay, one of Longboat Key's most sought-after waterfront communities. Perfectly positioned between the sparkling waters of Sarasota Bay and the pristine Gulf beaches, this completely renovated 2-bedroom, 2-bath villa offers an exceptional blend of modern elegance, resort-style amenities, and the coveted island lifestyle buyers dream about. Fully reimagined and rebuilt from the studs, this stunning residence showcases high-end craftsmanship and designer finishes throughout. Every detail has been thoughtfully upgraded, including brand-new electrical systems, plumbing, drywall, insulation, kitchen, bathrooms, fixtures, and finishes—providing the peace of mind and comfort of essentially new construction within an established waterfront community. The bright, open-concept floor plan is flooded with natural light and designed for effortless indoor-outdoor living. The beautifully appointed chef's kitchen flows seamlessly into the living and dining areas, creating an inviting space ideal for entertaining, seasonal gatherings, or everyday enjoyment. A dedicated 220-volt outlet offers convenient electric vehicle charging, adding modern functionality and future-ready convenience. One of the villa's most desirable features is its easy ground-level access with no stairs, making everyday living simple and accessible. Pet lovers will appreciate Windward Bay's generous pet-friendly policy allowing up to two pets, a rare and highly desirable amenity on Longboat Key. Step outside to your private patio retreat surrounded by lush tropical landscaping and mature greenery. Enjoy peaceful mornings with coffee, spectacular sunset skies, and relaxing evenings gathered around the fire pit just moments from beach access. The Gulf of Mexico is only steps away, offering endless opportunities for shelling, beach walks, swimming, paddleboarding, and breathtaking sunsets. Residents of Windward Bay enjoy an unmatched collection of resort-style amenities set across nearly 27 acres of beautifully maintained waterfront property, including: Three beach access points to the powdery sand beaches of Longboat Key. Nearly one-half mile of scenic waterfront walking paths and nature trails. Two heated swimming pools. Six tennis and pickleball courts. Fitness center, sauna, clubhouse, library, and social gathering spaces. Two private marinas with boat slips and jet ski slips (for rent and subject to availability). Private fishing pier with panoramic bay views. Kayak storage and launch areas. Outdoor grilling stations, fire pits, and waterfront gathering areas. Lush park-like grounds with mature tropical landscaping. Whether you're searching for a primary residence, seasonal retreat, second home, snowbird escape, waterfront villa, beach getaway, or investment opportunity, this move-in-ready residence offers an unparalleled combination of location, lifestyle, and value. Ideally located minutes to St. Armands Circle, Sarasota's vibrant arts and dining scene, championship golf courses, boating destinations, waterfront restaurants, and world-renowned Gulf Coast beaches, this exceptional property delivers the very best of Longboat Key living. Experience the ultimate in island living where luxury, comfort, boating, beach access, and resort-style amenities come together in one extraordinary coastal retreat.

4720 Gulf Of Mexico Drive Unit Villa 2, Longboat Key

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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