Windward Bay Homes with Community Pool type

Windward Bay Homes with Community Pool type

Welcome to Windward Bay, a stunning waterfront subdivision nestled in the charming Longboat Key, Florida, within the picturesque Manatee County. This serene community is a hidden gem, offering residents a perfect blend of tranquility and coastal living, making it an ideal location for families, retirees, and anyone looking to embrace a laid-back lifestyle.

Windward Bay boasts a selection of beautifully designed homes, each exuding elegance and comfort. Many properties feature spacious floor plans, modern amenities, and breathtaking views of the surrounding landscapes. One of the standout features of this community is its inviting community pool, where residents can soak up the Florida sunshine, socialize with neighbors, or simply unwind after a long day. The pool area is beautifully landscaped, creating a perfect oasis for relaxation and recreation.

Living in Windward Bay means you’re just moments away from the pristine beaches of Longboat Key, renowned for their soft white sands and crystal-clear waters. Enjoy leisurely strolls along the beach, indulge in water sports, or savor delightful dining experiences at nearby restaurants. The community is also conveniently located near shopping centers, parks, and cultural attractions, ensuring that everything you need is within reach.

Whether you’re looking for a seasonal getaway or a permanent residence, Windward Bay offers a lifestyle that is both luxurious and laid-back. Come and discover the charm of this vibrant community, where every day feels like a vacation, and make Windward Bay your new home in paradise!

Newest Windward Bay Homes with Community Pool type

4830 Gulf Of Mexico Drive Unit Villa 11, Longboat Key
$525,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
TOTAL PEACE OF MIND INCLUDED! NEW KITCHEN! NEW FLOORING! NEW A/C! NEW WATER HEATER! BEACH ACCESS & RESORT-STYLE AMENITIES! ZERO COMPROMISES! Nestled within the sought-after waterfront community of Windward Bay, this beautifully renovated corner villa places you just steps from the Gulf of Mexico and just steps from Sarasota Bay. Privately situated as an end-unit residence, this light-filled villa benefits from additional windows, enhanced privacy, and a bright, airy atmosphere that immediately feels like home. At the heart of the home, the completely renovated kitchen showcases beautiful new cabinetry, an inviting functional design, and a full suite of brand-new appliances. Two different finishes of porcelain plank tile flooring extend throughout the entire residence, creating a seamless coastal aesthetic that is both stylish and durable. The spacious living and dining areas flow comfortably for everyday living and entertaining, while the private outdoor patio offers the perfect place to enjoy morning coffee, evening cocktails, or simply relax in the gentle island breeze. Beyond the cosmetic improvements, this villa delivers exceptional value through major mechanical upgrades already completed. A new air-conditioning system and new water heater provide years of worry-free ownership and are backed by a transferable 10-year parts and service warranty. Even better, ownership includes two annual air-conditioning service visits, providing convenience and additional peace of mind. Living on the ground floor means easy access with no stairs or elevators to navigate and convenient parking just outside your door. Whether returning from the beach, enjoying a neighborhood walk, or unloading groceries, everyday living feels simple and carefree. The community itself has already completed significant Villa improvements, including hurricane-impact windows, hurricane-impact sliding glass doors, and a newer roof installed in 2020, offering both protection and confidence for years to come. Spread across 26 lushly landscaped waterfront acres, Windward Bay offers an impressive collection of resort-style amenities. Residents enjoy three beach access points, including one private deeded, a scenic half-mile walking trail, two heated swimming pools, fitness center, saunas, clubhouse, tennis courts, pickleball courts, kayak launches, covered parking, storage areas, and boat docks available by waitlist. Nature lovers will appreciate the abundance of wildlife that calls Windward Bay home. Dolphins, manatees, wading birds, and native coastal species are frequent sightings throughout the community's waterfront setting, creating a peaceful connection to the natural beauty of Sarasota Bay. Adding to its appeal, Windward Bay is pet-friendly, financially sound, and has successfully completed both its Milestone Inspection and Capital Reserve Study. Monthly fees have remained remarkably stable, reflecting responsible stewardship and strong long-term planning. Located near the center of Longboat Key, residents enjoy convenient access to St. Armands Circle, Downtown Sarasota, Bridge Street, championship golf courses, waterfront restaurants, boutique shopping, marinas, and the world-class arts and cultural venues that define Florida's Gulf Coast lifestyle. Modern updates, major system replacements, extensive community amenities, and an unbeatable location all come together in one exceptional island retreat. Villa 11, where every day feels like a vacation!

4830 Gulf Of Mexico Drive Unit Villa 11, Longboat Key
4700 Gulf Of Mexico Drive Unit 305, Longboat Key
$705,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
Welcome to your new home at Windward Bay, where sweeping panoramic views of Sarasota Bay, sophisticated modern finishes, and exceptional resort-style amenities come together to create your extraordinary coastal retreat. Perfectly positioned on the third floor, your turnkey furnished, two-bedroom residence captures breathtaking bay views from nearly every room. From rainbows to dolphins, from rafts of white pelicans to pods of frolicking dolphins, from the pink and blue shades of a coastal sunrise to the orange clouds of sunset, you’ll have a front-row seat to the ever-changing beauty of nature. Beautifully remodeled with today’s most desired finishes, your new residence features luxury rigid-core wood-look plank flooring, elegant crown molding, nature-inspired bath tiles, and an inviting open concept design that seamlessly connects the kitchen, dining and great room. The beautifully appointed chef’s kitchen showcases white quartz countertops, crisp white wood cabinetry with soft-close features, stainless steel appliances, a stylish tile backsplash, and a spacious breakfast bar ideal for casual dining and entertaining. Both bedrooms offer spectacular bay views through expansive sliding glass doors with integrated blinds, creating a peaceful connection to the surrounding coastal landscape. Your primary suite is a private sanctuary complete with an elegantly remodeled en-suite bathroom featuring dual vanities, stone-floored shower, and seamless glass enclosure. And you’ll love the spacious, walk-in California-style closet. Extensive improvements provide modern comfort and peace of mind, including PGT hurricane-impact windows (2019), a new air-conditioning system (2020), updated electrical, remote-controlled Hunter Douglas window treatments, an ecobee wireless thermostat, and an interior utility closet with a new washer and dryer. Additional conveniences include assigned under-building parking and a private storage closet full of everything you’ll need for a day at the beach. Set along the beautiful shores of Sarasota Bay, the recently renovated (2022/2023) Windward Bay complex is a waterfront community of just 151 residences offering new roofs and walkways, and an impressive collection of amenities. Boating enthusiasts will appreciate 28 first-come, first-served boat slips available for lease at just $30 per month, along with kayak storage, two kayak launches, and fish-cleaning stations. An easy three-minute walk to the uncrowded public access point, or a five-minute walk to the HOA’s deeded beach access point just across Gulf of Mexico Drive make enjoying the Gulf’s pristine beaches effortless. Residents also enjoy two heated swimming pools, tennis and pickleball courts, a fitness center, sauna, recently remodeled clubhouse with kitchen and library, barbecue grills, fire pits, outdoor dining areas, active community social committee and approximately half a mile of scenic walking paths. On-site management adds another layer of convenience. Ideally located near championship golf courses, marinas, waterfront dining, boutique shopping, St. Armands Circle, downtown Sarasota, and the vibrant new St. Regis Longboat Key Resort, this residence places the very best of island living within easy reach. Pet-friendly policies allow two pets weighing up to 75 pounds, while flexible rental opportunities, with a one-month minimum and up to two rentals annually, add investment appeal.

4700 Gulf Of Mexico Drive Unit 305, Longboat Key
4600 Gulf Of Mexico Drive Unit 301, Longboat Key
$660,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
Welcome to Paradise!  Fall in love with this turnkey furnished two- bedroom two bath End Unit condo! Relax and enjoy beautiful unobstructed views of Sarasota Bay from nearly every room in the house. The bright newly remodeled open concept kitchen has new cabinetry, quartz countertops and a large breakfast bar. You can even catch a sunset from the oversized westerly kitchen window. On the far side of the home is the master suite with an ensuite bath with a walk-in shower and dual sink vanity. The walk-in closet has built-in shelves and is large enough to accommodate the one-year-old stackable washer and dryer. The second bedroom has built in closets and drawers along with a built-in desk making it ideal for guests or a home office. Both bedrooms access the lanai that has an amazing view with its floor to ceiling windows. Additional features in the home include a whole house water filter, hurricane impact windows 2023, HVAC 2021, water heater 2022,microwave and range 2023 and a brand-new refrigerator. This home is extremely spacious and provides ample storage. There are two linen closets, three walk in closets and three sets of custom boudoir built-ins. There is also a ground level private storage room at your assigned under building parking space which happens to be located next to the Elevator. This condo is also located directly across from one of the community pools. Enjoy three beach access points (including one private), 26 acres of tropical surroundings including a 1/2 mile of nature trails, two heated pools, fitness center and sauna, clubhouse, tennis and pickleball courts, boat docks (waitlist) kayak launches, kayak storage and two marinas. You are also just minutes away from championship golf courses, restaurants, shopping, St. Armands Circle, Downtown Sarasota, and Anna Marie Island. This waterfront condo community and its great location has something for everyone to enjoy!

4600 Gulf Of Mexico Drive Unit 301, Longboat Key
4800 Gulf Of Mexico Drive Unit PH 3, Longboat Key
$795,000
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 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
4720 Gulf Of Mexico Drive Unit Villa 2, Longboat Key
$585,000
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
4750 Gulf Of Mexico Drive Unit Villa 8, Longboat Key
$649,900
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
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