Twin Oak Pond

Listings For SaleSold History and Market Report

Twin Oak Pond Homes for Sale – Siesta Key, Sarasota, Florida 34242

Twin Oak Pond

Take a short spin around Winding Way Road, if you’re searching for Sarasota real estate for sale in a laid-back neighborhood. This charming locality, just off Midnight Pass Road in the northeastern side of the eight-mile long Siesta Key, is the domain of the Twin Oak Pond subdivision.

Canopied by lush tropical trees, this community consists of 41 single family homes in a park-like setting. Here, you’ll find residences built from the late 1950s up to the early 2000s, some 80% of which are owner-occupied and the majority off-market.

Attractive price points

Twin Oak Pond

Nevertheless, the vibrant market for Siesta Key homes for sale has also permeated into this lovely community, with recent sales recorded at between the $300s and $600s price levels. These recently sold Twin Pond Oak residences have floor areas ranging from 1,466 square feet up to 3,046 square feet designed with three bedrooms.

At the $300s price range, buyers of Siesta Key homes for sale are likely to encounter fixer-uppers built in the 1960s. Typically, these houses would feature two bedrooms and two baths within floor areas of about 1,300 square feet.

The relatively fewer choices of available properties at Twin Pond Oak can likewise include homes priced around the mid-$500s. Typically, these are well-maintained three-bedroom homes built in the mid 1970s with a floor space of 2,100-plus square feet and a two-car garage.

Upper-tier Siesta Key homes for sale in this neighborhood would usually be in the high $600s. Also with square footage designed for three bedrooms and three baths, these houses’ later vintage, more contemporary design and gated courtyard with pool typically account for their higher pricing.

Convenient to lifestyle facilities

Twin Oak Pond

As could be expected from a quiet and sparsely populated neighborhood like Twin Oak Pond, this community is the favored choice of retirees and middle-aged adults. Nonetheless, smart rental property investors can also be drawn by an available residence in this community. Its homeowners can rent their residences in the community for a one-month minimum period.

Except for the neighborhood’s exquisite tropical landscape, Twin Oak Pond offers no common amenities for its residents. One great equalizer though is its superb location adjacent to Glebe Park with a playground, picnic areas and walking trail, as well as facilities for soccer, baseball and basketball. This park at the southern boundary of the neighborhood is home to the Suncoast Sports Club which regularly holds tournaments and camps for these sports disciplines as well as for flag football and lacrosse. As enticing, the pristine white beach which is a prime attraction for Siesta Key homes for sale is less than 30 minutes south of Twin Oak Pond.

Linked by the shady Canopy Road to Midnight Pass, Twin Oak Pond is also only a short drive away from many points of interest toward north. These include the one-acre Boyd Park and the newly renovated Bay Island Park, the northern gateway of Siesta Key which is a popular local fishing spot. A bit farther across Siesta Drive Bridge, shopping, dining and entertainment venues abound at the Southside Village, all just a few miles from similar lifestyle alternatives at downtown Sarasota.


Twin Oak Pond Homes for Sale

Below are the current real estate listings available at Twin Oak Pond

Please contact me if you would like to schedule a tour of any of the listed properties below.

MLS# A4151541 - Status: Active View Property Details Add to Favorites View Map

  • 5205 WINDING WAY
  • Price: $514,900
  • Zip Code: 34242
  • 1466 Square Feet
  • Subdivision: TWIN OAK POND
  • Bedrooms: 3 Baths: 2
  • Totally renovated and best priced 3 bedroom Single Family midcentury home on pond for Sale on Siesta Key!!! Walk to world Famous #1 Beach in the USA from your Canopied Street. Large Year Around Florida room and additional Screened-In Lanai, Granite ... Read More
  • Listing courtesy of: Key Realty

MLS# A4163466 - Status: Active View Property Details Add to Favorites View Map

  • 5206 WINDING WAY
  • Price: $415,900
  • Zip Code: 34242
  • 1155 Square Feet
  • Subdivision: TWIN OAK POND
  • Bedrooms: 2 Baths: 2
  • Currently the Lowest Priced Home on Siesta Key!! Great Siesta Key home a short walk to the sugary sands #1 Siesta Key Beach. This beautiful home is fully remodeled, which is first apparent in the all new Stucco, Paint, and Custom Woodwork on the Home ... Read More
  • Listing courtesy of: RE/MAX Tropical Sands