Winding Oaks (Bay Isles)
Explore Winding Oaks, an elegantly designed community that offers a nature park, golf course views, and a full social calendar.
Duplex Condominiums
2,000 - 2,700
$700s - $1M
A two-car garage with every home
About Winding Oaks
Winding Oaks is a community of duplex condominiums behind the Bay Isles gates in Longboat Key. Each condominium comes with its own two-car garage. Homes run from about 2,000 square feet up to about 2,700. Open floor plans, high ceilings, and wide screened lanais are standard, and many homes look out over a lagoon or the Harbourside golf course.
The setting does a lot of the work here. The community pool sits at the center of the community, ringed by a beautiful nature park. Many homes also have a walled private courtyard, and some owners have added a pool and spa of their own.
Winding Oaks keeps one of the fullest social calendars on the island. Neighbors gather at the pool and at the beach. Activities and clubs are plentiful. They include book clubs, writing clubs, gaming clubs, monthly lunches, group outings, and an end-of-season party. The association handles the roofs, the exterior paint, the grounds, and the building insurance, so owners can lock the door and travel. Ownership includes membership in the private Bay Isles Beach Club on the Gulf, and membership to the Longboat Key Club is optional, adding golf, tennis, fitness, and dining.
Amenities in Winding Oaks
Beach Access
No
Private Beach
No
Boat Slips
No
Marina Nearby
Yes
Beach Club Access
Yes
Clubhouse
No
Community Pool
Yes
Fitness Center
No
Walking Paths
No
Golf Nearby
Yes
Tennis
No
Lifestyle Activities
Yes
Pickleball
No
Maintenance Included
Yes
Gated
Yes
55+ Community
No
Visual Tour of Winding Oaks (Bay Isles)
Nearby Communities in Longboat Key
Corey’s Landing is a gated Bay Isles neighborhood featuring a community pool and tennis, with a mix of bayfront and golf-course-oriented properties. It’s great for those who want a residential neighborhood vibe inside Bay Isles while staying close to Longboat Key Club amenities.
Sabal Cove is a gated neighborhood of 38 custom single-family homes inside Bay Isles on Longboat Key. Each home is one of a kind, set behind lush landscaping and beside a quiet lagoon. Owners enjoy access to the private Bay Isles Beach Club and optional membership to the Longboat Key Club.
The Bayou is a gated neighborhood of 126 custom single-family homes inside Bay Isles on Longboat Key. Several homesites sit on the Bay Isles Waterway, while many others line the golf course or have lake views. Residents enjoy deeded access to the private Bay Isles Beach Club and optional membership to the Longboat Key Club.
Queens Harbour is a gated waterfront community of single-family homes inside Bay Isles on Longboat Key. Residents enjoy maintenance-free living, a heated community pool, and deeded access to the private Bay Isles Beach Club. Homes offer beautiful views of Sarasota Bay, community lakes, or the golf course. Some homes also include private docks.
