Windward Bay Homes with Private Pool type

Windward Bay Homes with Private Pool type

Welcome to Windward Bay, an exquisite subdivision nestled in the heart of Longboat Key, Florida. This stunning community offers a serene coastal lifestyle, where the sun-kissed shores and gentle sea breezes create a perfect backdrop for your dream home. Windward Bay is renowned for its picturesque views, lush landscaping, and a welcoming atmosphere that makes it an ideal place for families, retirees, and anyone seeking a tranquil retreat.

One of the standout features of homes in Windward Bay is the inclusion of private pools. Imagine stepping into your own backyard oasis, where you can relax, entertain, or enjoy a refreshing swim in the privacy of your home. These luxurious private pools are designed to complement the stunning Florida weather, providing a perfect space for sunbathing, hosting barbecues, or simply unwinding after a long day.

The homes in Windward Bay boast a variety of architectural styles, ensuring that you'll find the perfect match for your personal taste. Each residence is thoughtfully designed with modern amenities, spacious layouts, and high-quality finishes, making them ideal for both comfortable living and elegant entertaining. With the beach just a stone's throw away, residents can easily indulge in the sun, sand, and surf that Longboat Key is famous for.

Living in Windward Bay means embracing a lifestyle of leisure and luxury. Enjoy nearby shopping, dining, and recreational activities, all while being part of a vibrant community. Discover the enchanting charm of Windward Bay—where your dream home with a private pool awaits!

Newest Windward Bay Homes with Private Pool type

4 Beds ⋅ 3 Baths ⋅ Windward Bay SubDv. ⋅ 34219 Zip Code

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. ⋅ 34228 Zip Code

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

2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code

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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