Windward Bay Homes for Sale

Windward Bay Homes for Sale

Welcome to Windward Bay, a hidden gem nestled in the picturesque Longboat Key, Florida. This charming subdivision offers a perfect blend of tranquility and coastal living, making it an ideal destination for those seeking a serene escape or a permanent residence in paradise. With its stunning waterfront views and lush landscapes, Windward Bay is a place where every day feels like a vacation.

The community is renowned for its beautifully designed homes, which range from spacious villas to luxurious condos, each offering unique architectural styles and modern amenities. Many of these homes feature expansive balconies, perfect for soaking in the breathtaking sunsets over the Gulf of Mexico. With properties for sale in various price ranges, there’s something to suit every lifestyle and budget.

Residents of Windward Bay enjoy a wealth of amenities, including a sparkling community pool, tennis courts, and direct access to private beaches. The area is also surrounded by an array of recreational opportunities, from boating and fishing to biking along scenic trails. The vibrant local culture is just a stone’s throw away, with fine dining, boutique shopping, and art galleries in nearby St. Armands Circle and downtown Sarasota.

If you’re looking to invest in a home that offers both luxury and a laid-back lifestyle, Windward Bay is the perfect choice. Explore our listings today and discover your dream home in this idyllic Florida paradise. Whether you’re seeking a seasonal retreat or a year-round residence, Windward Bay is ready to welcome you home.

Newest Windward Bay Homes for Sale

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

4 Beds ⋅ 3 Baths ⋅ Windward Bay SubDv.

NO CDD-GATED-HALF ACRE+POOL&SPA Welcome to Windwater, one of Parrish’s gated communities offering spacious homesites, community amenities, and no CDD fees. Built in 2025 by Mattamy Homes, this Mesa Verde floor plan offers 4 bedrooms, 3 bathrooms, a dedicated dining room, flex room, and a 3-car garage across 2,575 square feet of thoughtfully designed living space. Situated on over a half-acre pie-shaped homesite, this property features a private swimming pool, hot tub, covered front porch, covered rear lanai, paver driveway, and extensive outdoor living areas. Hurricane-impact windows provide added durability and peace of mind. Inside, the open-concept layout connects the kitchen, dining area, and Great Room, creating a spacious setting for everyday living and entertaining. The kitchen is appointed with premium quartz countertops, abundant cabinetry, and a large center island overlooking the main living spaces. Luxury vinyl plank flooring extends throughout the home, enhancing both style and functionality. The triple-split floor plan offers privacy and flexibility. The owner’s suite is located at the rear of the home and includes a spacious en-suite bath and oversized walk-in closet. Bedroom two features its own private bath and walk-in closet, while bedrooms three and four share a full bath. A versatile flex room near the foyer can be utilized as a home office, media room, fitness space, or additional living area. Additional highlights include epoxy flooring in the 3-car garage, generous storage throughout, and a premium homesite location within the community. Residents of Windwater enjoy gated access, a community pool, and convenient proximity to shopping, dining, recreation, and highly regarded schools. Located in the growing Parrish area with easy access to I-75, Lakewood Ranch, Sarasota, St. Petersburg, and Tampa. Schedule your private showing today and experience all that this nearly new Mattamy Homes Mesa Verde has.

5322 124th Avenue E, Parrish

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

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