Windward Bay Homes with Street Lights Community Features

Welcome to Windward Bay, an enchanting subdivision nestled in the picturesque Longboat Key, Florida. This serene community, located in Manatee County, offers the perfect blend of coastal charm and modern living, making it an ideal destination for those seeking a tranquil retreat by the sea.

Windward Bay is characterized by its beautiful homes surrounded by lush landscapes and scenic waterways, creating a picturesque environment that feels like a vacation every day. The community is designed with your comfort in mind, featuring well-maintained streets illuminated by charming street lights that enhance the neighborhood's inviting atmosphere. Evening strolls become a delightful experience as you bask in the warm glow of the lights, making it easy to connect with neighbors and enjoy the beauty of your surroundings.

Residents of Windward Bay enjoy a host of community features that foster a sense of belonging and camaraderie. The well-appointed amenities include a sparkling swimming pool, tennis courts, and access to private docks, perfect for boating enthusiasts eager to explore the stunning Gulf waters. With nearby beaches just a stone's throw away, beachcombing and sun-soaked afternoons are always within reach.

Longboat Key is renowned for its upscale living, offering an array of fine dining, boutique shopping, and cultural attractions. Windward Bay is not just a place to live; it’s a lifestyle choice that allows you to embrace the best of Florida living. Come discover your dream home in this idyllic community, where every day feels like a getaway!

Newest Windward Bay Homes with Street Lights Community Features

$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

$680,000

3 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code ⋅ A4679944 MLS ⋅ Active Status ⋅ 'J' BLDG.

THE BAY! THE GULF! THE BEST OF BOTH! Imagine a place where every day begins with the peaceful beauty of Longboat Key's sparkling bay and ends beneath the breathtaking colors of a Gulf Coast sunset. Perfectly positioned between both shores, this beautifully updated 3-bedroom, 2-bath end-unit villa offers the rare opportunity to experience the very best of island living from one exceptional location. Nestled within the highly sought-after waterfront community of Windward Bay, this 1,504-square-foot residence welcomes you with a sense of light, warmth, and effortless coastal elegance. As an end unit, the villa enjoys additional windows, enhanced privacy, and an abundance of natural sunlight throughout the day. Luxury vinyl plank flooring flows seamlessly through the living spaces, while custom plantation shutters add timeless character and refinement. The thoughtfully renovated kitchen blends style and functionality with granite countertops, beautiful soft-close cabinetry, and an inviting layout designed for everyday living and easy entertaining. The spacious great room opens effortlessly to a private outdoor patio, creating the perfect setting for morning coffee, afternoon relaxation, or dining beneath the coastal breeze. Life here is refreshingly simple. Ground-level living means no stairs, no elevators, and convenient parking just steps from your front door. Whether you're arriving home from the beach or carrying in groceries, everything about this villa is designed for easy, maintenance-free living. Equally impressive are the community improvements already in place. In 2020, the exterior was upgraded with hurricane-impact windows, hurricane-impact sliding glass doors, and a new roof, providing valuable peace of mind for years to come. Windward Bay has long been one of Longboat Key's most treasured communities, and it's easy to understand why. Set across 26 beautifully landscaped waterfront acres, residents enjoy three beach access points, a scenic half-mile nature trail, two heated swimming pools, fitness center, sauna, clubhouse, tennis and pickleball courts, kayak launches, covered parking, storage areas, and boat docks available by waitlist. Dolphins, manatees, tropical birds, and other native wildlife are frequent visitors, making every walk through the community feel like a nature retreat. Pet-friendly and financially strong, Windward Bay has completed both its Milestone Inspection and Capital Reserve Study. Monthly fees were reduced in 2025 and increased by only $13 for 2026, reflecting responsible community management and long-term stability. From this ideal location, you're just minutes from St. Armands Circle, Downtown Sarasota, Bridge Street, championship golf, waterfront dining, boutique shopping, and the exceptional arts and cultural attractions that make Florida's Gulf Coast so desirable. More than a beautiful villa, this is a lifestyle defined by sunshine, serenity, and connection to the water. A place where morning bay views, evening Gulf sunsets, and the ease of resort-style living become part of your everyday experience. THE BEST OF LONGBOAT KEY ISN'T ON THE BAY OR THE GULF... IT'S BETWEEN THEM. Welcome Home to Villa 8 at Windward Bay.

4750 Gulf Of Mexico Drive Unit Villa 8, Longboat Key

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