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Windward Bay | Longboat Key

Windward Bay offers a serene and picturesque waterfront lifestyle, ideal for those who appreciate the beauty of nature and the tranquility of coastal living.

Nestled along the edge of Sarasota Bay and just steps away from the pristine beaches of the Gulf of Mexico, this community provides a perfect blend of relaxation and outdoor activity.

Overview

Address: 4888 Gulf of Mexico Dr, Longboat Key, FL 34228
Total Units:151 units (7 condo buildings, 25 villas)
Year Built:1974-1975
Square Feet:912-1900 sq ft
Minimum Lease:1 month
Lease per Year2x per year
PetsYes, restrictions apply

Windward Bay Condos for Sale

About Windward Bay

Once residents experience the serene waterfront lifestyle and the unparalleled amenities that Windward Bay offers, they find it hard to leave.

The charm of Windward Bay has attracted a diverse group of residents who share a common passion for coastal living and the beauty of Sarasota Bay. Here are five reasons why buyers will fall in love with this unique Longboat Key community.

one

The Lifestyle

Nestled along over 20 acres of bayfront natural grounds, Windward Bay is a community that offers residents a beautifully landscaped environment and a half-mile of scenic waterfront trails. These trails are perfect for leisurely strolls, surrounded by mature tropical foliage.


two

Prime Bayfront Location

Windward Bay is perfectly situated along the scenic bayfront, offering residents a front-row seat to the natural beauty that defines coastal living. The community is a haven for nature enthusiasts, where you can indulge in bird watching or marvel at playful dolphins gliding through the waters.

The south marina often becomes a gathering spot for gentle manatees, adding to the tranquil and captivating environment. This unique location not only provides breathtaking views but also offers a daily connection to the vibrant marine life that makes Longboat Key so special


three

Three Pathways to Paradise

Windward Bay enjoys a prime location just across the street from the stunning blue-green waters and soft sands of the Gulf of Mexico. Residents have the unique advantage of not just one, but three convenient beach access points—one deeded and two public—that lead directly to the serene, uncrowded shores.

This ideal positioning allows for effortless access to the Gulf’s pristine beaches, making it easy to enjoy a day of sun, sand, and sea whenever the mood strikes.


four

Paws and Paradise

Windward Bay is a pet-friendly community that warmly welcomes your furry companions. Residents are allowed to have up to two pets, but it’s important to note that this can’t include two dogs. You can have one dog, up to 75 pounds, paired with another pet, such as a cat. While dogs are welcome, there are specific breed restrictions in place.

Read more: A Guide to Local Dog Parks and Beaches


five

Community Perks

Windward Bay offers a wealth of amenities designed to enhance the lifestyle of its residents. The community features two tennis and pickleball courts, perfect for staying active and socializing with neighbors.

For water enthusiasts, there are two marinas with 28 boat and jet ski slips available for a nominal monthly fee on a first-come, first-served basis, along with a fishing pier and two fish cleaning stations for those who enjoy a day on the water.

Kayakers will appreciate the convenient storage racks, while those looking to relax can take a dip in one of the two heated pools or challenge friends to a game of shuffleboard.

The clubhouse serves as a central hub with a fully-equipped kitchen, a cozy library, a well-appointed fitness room, a meeting space, and two soothing saunas.

Additionally, the south end of the community features a fire pit, offering a perfect spot for evening gatherings under the stars. With these top-notch amenities, Windward Bay truly caters to a luxurious and active coastal lifestyle.

Life on Longboat Key

Windward Bay is ideally situated in mid Longboat Key, offering residents the perfect balance of accessibility and tranquility. Nestled between Manatee and Sarasota Counties, this location provides easy access to both Sarasota and Bradenton.

Just a short drive from Windward Bay, you can explore the vibrant St. Armands Circle, Lido Key, and downtown Sarasota, as well as the charming areas of Bradenton Beach, Holmes Beach, and Anna Maria Island.

Windward Bay residents benefit from the nearby Shoppes of Bay Isles, which include essential conveniences like CVS pharmacy, nail salon, and Publix, the island’s only grocery store.

Dive Deeper: Uncover the mid-key lifestyle and commute insights


Windward Bay Photos


Which Longboat Key Community Best Fits Your Lifestyle?

Whether you are considering relocating to Longboat Key as a part-time resident or looking for your forever home within
this slice of paradise, take our quiz to discover which area of the island best complements your lifestyle.

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