When driving through the narrow barrier island of Longboat Key, it is easy to think that all neighborhoods are located on either side of the main thoroughfare, Gulf of Mexico Drive, but this does not reflect the totality of this attractive housing market. Winding Oaks is not a neighborhood you can see from Gulf of Mexico Drive; it is located in the bayous of Longboat Key, tucked away in an islet surrounded by a lagoon.

The architectural style at Winding Oaks Longboat Key is unique; this is one of the few neighborhoods in Southwest Florida where you can find Nantucket homes. There are only 56 units in this community, and each of them provides waterfront views. As part of the Bay Isles and Longboat Key Club development, residents of Winding Oaks have exclusive and deeded access to the beach across Gulf of Mexico Drive.

Floor plans in this neighborhood are spacious and filled with extras such as private courtyards and enclosed porches where you can enjoy views of the lagoon or a central pond. In the winter, when the water temperatures drop in the Sarasota Bay, manatees will spend more time in the lagoon to the delight of residents. The coziest two-bedroom units are built on 2,000 square feet of interior. Even though the units are paired villas, they provide the privacy and space of single-family homes, but maintenance is covered by homeowners association fees.

The tropical landscaping and stylish architecture give this community a resort-like ambiance. Homeowners can choose between the public beach across the road or their private stretch of sand located about a mile south within the Longboat Key Club, where they can also enjoy showers, a pavilion, beach volleyball, and a grilling area for picnics. Ownership also provides a discount on golf and tennis memberships at the exclusive Longboat Key Club.

Another advantage of living at Winding Oaks Longboat Key is being able to walk down to the only shopping center on the island, and this is where you can shop at Publix and CVS. As of late 2024, listings started at $1.2 million for a two-bedroom unit, but a more attractive unit with three bedrooms, two bathrooms, a private swimming pool, and spa was listed for $1.4 million. Latest pricing at Winding Oaks Longboat Key will be found below if there is inventory.