Winding Oaks

Ultra Plush Living in Winding Oaks

If you're spending time looking at luxury homes and luxury condominiums for sale in southwest Florida, maybe you've wondered: How can you combine the ease and convenience of condominium living with the benefits of a traditional neighborhood of single-family homes? Winding Oaks may be the unique answer. It's the setting for 56 ultra-plush, contemporary townhomes in 28 attractively-designed buildings. Winding Oaks is also a prestigious townhome community designed and laid out like a traditional-yet-stylish neighborhood of single-family homes. It's the "best of both worlds" and it's part of the greater Bay Isles community located in the Longboat Key Club on captivating Longboat Key.

Roomy Town Homes Set in Longboat Key Club

Most of the townhomes at Winding Oaks feature open, roomy floor plans, plenty of bright natural lighting and glass, a 2-car garage, pool, spa, courtyard, patio, and garden. Winding Oaks and all the Bay Isles neighborhoods are set inside the prestigious Longboat Key Club, which features 2 challenging, championship golf courses, 20 tennis courts at the award-winning Tennis Gardens, and a state-of-the-art spa and fitness center. Winding Oaks is also only a brief walk from the Gulf of Mexico and the 11 sun-drenched miles of sparkling white-sand beaches that grace beautiful Longboat Key. With an average year-round temperature of 73 degrees, at Winding Oaks you can enjoy the great Florida outdoors almost every day.

Winding Oaks sits near the center of Longboat Key, which means residents and guests are near other beautiful barrier islands as well as the thriving cities of Bradenton and Sarasota. St. Armand's Key is well-known for its superlative shopping and dining options, while Siesta Key is the home of Siesta Beach. Winding Oaks combines the best of traditional neighborhoods and condo communities, offers a great, active Florida lifestyle, an ideal climate, and a perfect location. You may not need to look elsewhere.


Entrance at Winding Oaks Drive and Harbourside Drive. Winding Oaks is east of Harbourside Drive, near the midpoint of the island. Longboat Key, FL 34228

Home Styles:

Single-story 2BR and 3BR plush, luxury townhomes in 2-unit buildings.


Winding Oaks sits near the center of Longboat Key. All townhomes offer pond, lagoon, or golf course views, and it's only the briefest walk to either Sarasota Bay or to the Gulf of Mexico.


Manned, gated 24-hour security; 2-car garages. Many of the townhomes also feature a pool, spa, patio, and much more. Winding Oaks is in the Longboat Key Club, which features 2 championship, 18-hole golf courses, 20 tennis courts, and a state-of-the-art fitness center. Pets are welcome but must be leashed in public areas.


St. Armand's Key and Siesta Key, Gulf of Mexico and the Gulf beaches, Bradenton and Sarasota.






Homes For Sale in Winding Oaks:

Longboat Key listing A4211656

City: Longboat Key
Price: $630,000
Beds: 2, Baths: 2
More Info

Longboat Key listing A4210727

City: Longboat Key
Price: $875,000
Beds: 3, Baths: 3
More Info

Longboat Key listing A4207814

City: Longboat Key
Price: $599,000
Beds: 2, Baths: 2
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Longboat Key listing A4400250

City: Longboat Key
Price: $845,000
Beds: 3, Baths: 3
More Info

Homes For Sale Winding Oaks


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