Twin Oak Pond

Are you looking for exclusivity and privacy when thinking of your ideal residency? Do you want a charming neighborhood with a canopied road to drive down every evening? How about access to the world’s softest sands and allure of the quaint, Siesta Village on a minute’s whim? You can have all of this in one upscale, unique community that exudes quality over quantity. With under 50 homes in totality, Twin Oak Pond is a quiet gem situated in the heart of Siesta Key.

Twin Oak Pond is one of those areas where buyers wait for homes to go on the market. Many homeowners have lived there for years and properties are coveted for good reason. Situated on the northeastern end of Siesta Key, all the amenities of the island lifestyle are at hand, but home life is quiet and special in this enclave. Nearby Glebe Park is a huge draw for families and retirees who enjoy watching an outdoor game on the weekends or who might enjoy some mid-morning exercise with friends in a beautiful outdoor space. Homes in Twin Oak Pond range from 1950’s architecture to modern Key-West style. With lush tropical landscaping and the canopy effect, residents feel like they are living in their own magical forest, smack dab in the heart of Siesta Key, one of the most beautiful islands on the planet.

Where is Twin Oak Pond?

Homes for sale in Twin Oak Pond

Active Sales


5205 WINDING WAY, Sarasota, FL, 34242-1861

1466 ft²
2 / 0

Listings courtesy of Key Realty


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Pending sales

There are currently no properties available at this time.


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Recently Sold


5234 WINDING WAY, Sarasota, FL, 34242-1848

1308 ft²
2 / 0

Listings courtesy of ASCENDIA REAL ESTATE


5208 WINDING WAY, Sarasota, FL, 34242-1848

1384 ft²
2 / 0



View ALL "Recently sold" homes in Twin Oak Pond

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Siesta Key Farmers Market: The Place To Be On Sundays

They’re at the delightful Siesta Key Farmers Market, a Sunday morning institution on Siesta Key that can draw as many as 2,000 participants. Local venders display and sell fresh-cut flowers, soaps, coffee, teas, pastries, breads, cheeses, jellies, sauces, seafood, and sandwiches. You can view exquisite, delicate orchids, and you’ll have a chance to enjoy scrumptious cookies and cakes.
- True Siesta Key

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