Windward Bay Homes with Community Mailbox Community Features

Welcome to Windward Bay, a picturesque subdivision nestled in the heart of Longboat Key, FL. This charming community is located in Manatee County, offering residents the perfect blend of tranquility and convenience.

Windward Bay is a hidden gem for those seeking a peaceful waterfront lifestyle. With its prime location on the stunning Longboat Key, residents can enjoy breathtaking views of the Gulf of Mexico and Sarasota Bay. The neighborhood is known for its well-maintained homes and lush landscaping, creating a serene and inviting atmosphere for all who call it home.

One of the standout features of Windward Bay is its Homes with Community Mailbox Community. This unique setup fosters a sense of community among residents, making it easy to connect with neighbors and build lasting relationships. From shared mailboxes to community events, this feature adds a special touch to everyday life in Windward Bay.

In addition to its beautiful homes and community amenities, Windward Bay offers easy access to a variety of outdoor activities, including boating, fishing, and beachcombing. Residents can also take advantage of nearby shopping, dining, and entertainment options, ensuring there is always something to do just minutes from home.

Experience the best of coastal living at Windward Bay, where every day feels like a vacation. Come and discover why this waterfront community is a true hidden paradise on Longboat Key.

Newest Windward Bay Homes with Community Mailbox Community Features

$595,000

2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code ⋅ A4704578 MLS ⋅ Active Status ⋅ 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 ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code ⋅ A4704564 MLS ⋅ Active Status ⋅ 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

$725,000

2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code ⋅ A4689724 MLS ⋅ Active Status ⋅ C504 BLDG.

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

$585,000

2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code ⋅ A4679458 MLS ⋅ Active Status ⋅ K BLDG.

Completely renovated two-bedroom and two-bathroom walkout (no stairs to take) on Longboat Key! 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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