Windward Bay Real Estate

Windward Bay Real Estate

Welcome to Windward Bay, a hidden gem nestled in the heart of Longboat Key, Florida. This picturesque subdivision is a true testament to coastal living, offering residents an idyllic blend of tranquility and vibrant community life. With its prime location in Manatee County, Windward Bay is perfectly situated between the stunning Gulf of Mexico and the serene waters of Sarasota Bay, making it a paradise for beach lovers and nature enthusiasts alike.

Windward Bay features a collection of beautifully designed condos and townhomes, each exuding charm and sophistication. Residents enjoy spacious living areas, modern amenities, and breathtaking views that capture the essence of Florida’s coastal beauty. The lush, landscaped grounds provide an inviting atmosphere, perfect for leisurely strolls or morning jogs.

One of the standout features of Windward Bay is its impressive array of community amenities. Dive into relaxation at the sparkling community pool, or indulge in a friendly match on the tennis courts. For those who love the outdoors, the nearby beaches offer endless opportunities for sunbathing, swimming, and water sports. Additionally, the community is just a short drive from the vibrant dining and shopping experiences that Longboat Key and the surrounding areas have to offer.

Living in Windward Bay means embracing a lifestyle filled with sunshine, stunning sunsets, and a welcoming community spirit. Whether you’re looking for a seasonal retreat or a permanent residence, Windward Bay is the perfect place to call home. Discover your slice of paradise today and experience the unparalleled charm of Longboat Key living!

Newest Listings in Windward Bay

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

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

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

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

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

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

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

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

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

Start Your Search