Winding Oaks is an exclusive and gated community with 56 Nantucket-style, maintenance-free homes. Deeded beach access is available to all homeowners through the Bay Isles Beach Club.
Below are all of the homes for sale in the Winding Oaks neighborhood on Longboat Key Florida. All listings are updated daily from the Multiple Listing Service (MLS).
To learn more about any of these homes or receive email updates when new properties hit the market, simply give us a call at 941-544-6467 or send us an email. We are here to help!
| Total Listings: | 2 |
| Average Price: | $1,049,500 |
| Highest Price: | $1,150,000 |
| Lowest Price: | $949,000 |
| Average Size: | 2,582 ft² |
| Average Price Per Square Foot: | $406 per ft² |
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Tucked Within Winding Oaks, One Of Longboat Key’s Most Sought-after Villa Communities, This 3br/3ba Residence Offers The Scale And Comfort Of A Single-family Home Paired With The Simplicity Of Maintenance-free Living. From The Paver Drive And Walk...
Own Your Own Slice Of Tropical Paradise On Longboat Key With This Beautiful Two Bedroom Two And On Half Bath Villa In The Exclusive Winding Oaks Community Located Behind The Gates Of Bay Isles Association. Sweeping Views Of The Longboat Key Club...
All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.
Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.
Listing data comes from My Florida Regional MLS DBA Stellar MLS.
Listing information last updated on June 6th, 2026 at 8:52pm EDT.
