Windward Bay Homes with Shingle Roof

Windward Bay Homes with Shingle Roof

Welcome to Windward Bay, a hidden gem nestled in the picturesque Longboat Key, Florida. This charming subdivision offers an idyllic coastal lifestyle, where serene bay views meet the vibrant energy of the Gulf of Mexico. With its prime location in Manatee County, Windward Bay is a haven for those seeking the perfect blend of relaxation and recreation.

The homes in Windward Bay are a stunning reflection of coastal elegance, featuring classic shingle roofs that not only enhance their aesthetic appeal but also provide durability and protection against Florida’s varied weather. Each residence is designed with an emphasis on spaciousness and natural light, creating inviting interiors that seamlessly blend with the beauty of the surrounding landscape. Imagine enjoying your morning coffee on a sun-drenched patio, or hosting gatherings in your airy living space, all while basking in the gentle sea breeze.

Living in Windward Bay means you’re just moments away from pristine beaches, world-class dining, and a plethora of outdoor activities. Whether you prefer kayaking in the bay, strolling along the beach, or indulging in the local arts scene, there’s something for everyone. The community is known for its friendly atmosphere, making it easy to forge lasting connections with neighbors who share your passion for the coastal lifestyle.

Discover the charm of Windward Bay, where every day feels like a vacation. Experience the perfect balance of luxury and comfort in this remarkable Longboat Key community, and make your dream of coastal living a reality. Welcome home!

Newest Windward Bay Homes with Shingle Roof

$595,000
2 Beds ⋅ 2 Baths ⋅ A4704578 MLS ⋅ F BLDG.
Welcome to your island retreat, an impeccably renovated 2-bedroom, 2-bath residence offering the best of Longboat Key living with beautiful views of the preserved mangroves and Sarasota Bay. Renovated from top to bottom, this home has been thoughtfully transformed and is available TURNKEY FURNISHED with hurricane impact windows and shutters for a peace of mind. 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. A Murphy bed in the office area adds even more versatility, providing the perfect setup for overnight guests while still allowing the space to function as a home office.Living at Windward Bay means embracing the Longboat Key lifestyle from both the BAY AND THE BEACH. Enjoy three beach access points directly across the street for effortless days along the Gulf, while boat slips available to residents make it easy to get out on Sarasota Bay and explore the surrounding waterways. Windward Bay is a PET-FRIENDLY, amenity-rich waterfront community offering multiple swimming pools, tennis and pickleball courts, a fitness center with sauna, kayak storage, and scenic walking paths along the bayfront. Ideally situated on Longboat Key, you are just minutes from exceptional restaurants and shopping, St. Armands Circle, Anna Maria Island, and everything Sarasota has to enjoy. With FULLY FUNDED RESERVES FOR 2026, NO UPCOMING SPECIAL ASSESSMENTS, and a PASSED MILESTONE INSPECTION, this move-in-ready residence offers the renovations, amenities, location, and peace of mind today's Florida condo buyer is looking for. Your Longboat Key lifestyle awaits!

4540 Gulf Of Mexico Drive Unit 204, Longboat Key
$799,999
2 Beds ⋅ 2 Baths ⋅ A4704564 MLS ⋅ Windward Bay BLDG.
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
$755,000
4 Beds ⋅ 3 Baths ⋅ A4696886 MLS
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
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