Winding Oaks CONDO HOMES on beautiful Longboat Key, Florida
Water Views Everywhere
High Ceilings, Open Plans
High Ceilings, Open Plans
Every two or three bedroom Winding Oaks home is on one level and has a pond or lagoon view, private courtyard and deck. Some even have private pools and spas.
High Ceilings, Open Plans
High Ceilings, Open Plans
High Ceilings, Open Plans
Live with light and height and privacy. Ceilings in the living and dining area are 14-feet at their highest point. Windows and sliders on two sides bring the outdoors inside. Each building includes two units with the privacy of a single family home or a private villa.
Private Front Courtyards
High Ceilings, Open Plans
Private Front Courtyards
Open the front gate of each of the 56 homes and delight in private landscaped courtyards. Most owners tailor their garden to their style and then have the Association maintain it.
Well Maintained
Warm and Welcoming
Well Maintained
The Association maintains the community pool and the exteriors of our homes, the landscaped courtyards and common area gardens. A fully funded reserve is at the ready for future capital improvements.
Pet Friendly
Warm and Welcoming
Well Maintained
Winding Oaks is one of the few Longboat Key communities that embrace pets. The morning dog walkers enjoy the paved two mile sidewalk that spans the length of the Bay Isles.
Warm and Welcoming
Warm and Welcoming
Warm and Welcoming
We enjoy many opportunities to socialize including monthly luncheons, the annual winter cocktail party, end-of-season beach party, pool parties and road trips. You choose how social you want to be—very, somewhat, or not at all.
Who, When and Where
Private Beach Access
Private Beach Access
Some neighbors work locally or remotely. Others are retired. We include award-winning teachers, authors, medical professionals, realtors, financial advisors, artists, executives, engineers and entrepreneurs—from the U.S., Canada, the UK and Europe. We are a community of texture—not everyone is the same. Some live here full-time, others seasonally.
Private Beach Access
Private Beach Access
Private Beach Access
Winding Oaks is one of 19 subdivisions inside Bay Isles, a gated community surrounded by the Longboat Key Club Golf Course and a sparkling inland waterway. Winding Oaks owners enjoy all the beauty, security and benefits of Bay Isles including access to the private Bay Isles Beach Club on Gulf of Mexico Drive.
Centrally Located
Private Beach Access
Centrally Located
Winding Oaks is only one mile from public tennis courts, the U.S. post office, library, banks, houses of worship and the Town Shoppes of Bay Isles that include the only supermarket and pharmacy on Longboat Key. St. Armands Circle is less than six miles away to the South.