Winding Oaks is a secluded waterfront villa community located on the bay side of Longboat Key. Tucked away within the Bay Isles development, this unique neighborhood sits on a small island surrounded by lagoons and lush tropical landscaping, offering residents privacy and beautiful water views.

Unlike many communities along Gulf of Mexico Drive, Winding Oaks is hidden within the quiet bayous of the island. With only 56 residences, this boutique neighborhood provides a peaceful residential environment while still offering easy access to the beaches and amenities that make Longboat Key one of the most desirable barrier islands in Southwest Florida.

Winding Oaks Longboat Key Villas

Homes in Winding Oaks feature a distinctive Nantucket-inspired architectural style rarely found in Southwest Florida. The residences are designed as spacious paired villas that provide the privacy and feel of single-family homes while offering the convenience of maintenance-free living.

Floor plans typically exceed 2,000 square feet and include features such as private courtyards, enclosed porches, and generous outdoor living spaces overlooking the lagoon or central pond. Many homes provide scenic waterfront views and opportunities to observe local wildlife, including manatees that frequently visit the warmer waters of the lagoon during cooler months.

The community’s charming design, spacious residences, and tranquil setting make Winding Oaks a unique residential option on Longboat Key.

Winding Oaks Community Amenities

Residents of Winding Oaks enjoy access to a variety of amenities through the Bay Isles and Longboat Key Club communities.

• Deeded private beach access across Gulf of Mexico Drive
• Access to the Bay Isles Beach Club
• Lagoon and waterfront views throughout the community
• Mature tropical landscaping
• Maintenance-free villa living

Ownership in Winding Oaks also provides the opportunity for discounted memberships to the Longboat Key Club’s golf and tennis facilities.

Nearby Beaches, Shopping and Attractions

Residents enjoy convenient access to the Bay Isles Beach Club located just across Gulf of Mexico Drive. This private beach area offers showers, picnic areas, volleyball courts, and beautiful views of the Gulf of Mexico.

The nearby Bay Isles Shopping Plaza provides everyday conveniences including Publix, CVS, and several restaurants. Residents can also visit the upscale shopping and dining district at St. Armands Circle or explore the cultural attractions of nearby Sarasota.

Boating, golf, tennis, and beach activities are all part of the Longboat Key lifestyle, making Winding Oaks an ideal community for those seeking both relaxation and recreation.

Villas for Sale at Winding Oaks on Longboat Key

With its waterfront setting, Nantucket-style architecture, and private beach access, Winding Oaks remains one of the more distinctive villa communities on Longboat Key. View current Winding Oaks Longboat Key villas for sale below if inventory is available.

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Winding Oaks Longboat Key FAQ

Where is Winding Oaks located?

Winding Oaks is located within the Bay Isles community on the bay side of Longboat Key.

How many homes are in Winding Oaks?

The community consists of approximately 56 villa-style residences.

What style homes are found in Winding Oaks?

Homes feature Nantucket-inspired architecture and spacious villa floor plans.

Do residents have beach access?

Yes. Residents have deeded access to the private Bay Isles Beach Club across Gulf of Mexico Drive.

Is shopping nearby?

Yes. The Bay Isles Shopping Plaza with Publix and CVS is located just a short walk from the community.