Winding Oaks is a private villa community located within the prestigious Bay Isles section of Longboat Key. Tucked away from Gulf of Mexico Drive on a quiet islet surrounded by lagoon waters, Winding Oaks offers a peaceful residential setting with spacious villas, waterfront views, and access to the Longboat Key Club lifestyle.
With only 56 residences, Winding Oaks has a secluded feel that appeals to buyers seeking privacy, maintenance-free living, beach access, and a unique bayou setting in the heart of Longboat Key.
Villas in Winding Oaks Longboat Key
Winding Oaks features paired villa-style residences with generous floor plans, waterfront views, and a distinctive architectural style inspired by classic Nantucket design. Although the homes are attached villas, many live more like single-family residences because of their size, privacy, courtyards, enclosed porches, and peaceful outdoor spaces.
Many villas offer views of the lagoon, central pond, tropical landscaping, or surrounding water features. Floor plans often include two- and three-bedroom layouts, open living areas, spacious primary suites, screened or enclosed lanais, private courtyards, and outdoor areas designed for enjoying the natural setting.
The lagoon setting is especially appealing during the cooler months, when manatees may be seen in the surrounding waters of the bayou and lagoon areas.
Community Amenities
- Private Bay Isles villa community
- Only 56 residences
- Waterfront and lagoon views
- Nantucket-inspired architecture
- Maintenance-free villa living
- Private courtyards and enclosed porches in select homes
- Deeded beach access through Bay Isles
- Access to Bay Isles Beach Club amenities
- Close proximity to Longboat Key Club
- Walking distance to Bay Isles shopping
Location
Winding Oaks is located within Bay Isles on the Sarasota Bay side of Longboat Key. This central island location places residents close to Bay Isles shopping, Longboat Key Club, marinas, golf, tennis, restaurants, beaches, and everyday conveniences.
Residents are also close to the private Bay Isles Beach Club on the Gulf side of Longboat Key, as well as St. Armands Circle, Lido Key, Downtown Sarasota, and the many waterfront destinations throughout the island.
Nearby Beaches and Attractions
Winding Oaks residents enjoy deeded access to the Bay Isles Beach Club, where they can relax on the Gulf beach, enjoy picnic areas, showers, a pavilion, grilling areas, and beach recreation.
Nearby destinations include Bay Isles, Longboat Key Club, St. Armands Circle, Lido Key, Downtown Sarasota, Longboat Key marinas, waterfront restaurants, and Sarasota Bay.
Similar Communities
- Harbour Oaks – Private Bay Isles neighborhood with villa-style residences, mature landscaping, and deeded beach access.
- Coreys Landing – Gated Bay Isles neighborhood with waterfront homes, villas, townhomes, and access to private beach amenities.
- Sabal Cove – Exclusive Bay Isles neighborhood with custom homes, waterfront views, and private beach club access.
- Bay Isles – Prestigious gated Longboat Key community offering private beach access, waterfront homes, condos, villas, and club amenities.
- Fairway Bay – Bay Isles condominium and townhome community with Sarasota Bay views, resort-style amenities, and convenient island access.
Photo Slideshow of Winding Oaks Longboat Key
Winding Oaks Villas for Sale | Longboat Key Florida
With its private Bay Isles setting, spacious villa residences, lagoon views, deeded beach access, and proximity to Longboat Key Club, Winding Oaks remains a desirable maintenance-free community on Longboat Key. View current Winding Oaks villas for sale below if inventory is available.
Winding Oaks Longboat Key FAQ
Where is Winding Oaks located?
Winding Oaks is located within the Bay Isles section of Longboat Key, Florida, on the Sarasota Bay side of the island.
What types of homes are in Winding Oaks?
Winding Oaks features spacious paired villa-style residences with waterfront, lagoon, pond, or tropical landscape views.
Does Winding Oaks have beach access?
Yes, Winding Oaks residents have deeded access to the private Bay Isles Beach Club on the Gulf side of Longboat Key.
How many residences are in Winding Oaks?
Winding Oaks includes 56 villa-style residences in a private Bay Isles setting.
What is near Winding Oaks Longboat Key?
Winding Oaks is close to Bay Isles shopping, Longboat Key Club, private beach amenities, marinas, restaurants, St. Armands Circle, Lido Key, and Downtown Sarasota.
