Twin Oak Pond, Siesta Key – Sarasota – For Sale

SiestaKeyRealtor - Joe Stephens (941) 400-9084 Communities 0

Twin Oak Pond Siesta Key For Sale


Twin Oak Pond is a canopy draped neighborhood of 37 single family homes. This quaint neighborhood is hidden off of Midnight Pass Road.

5238 WINDING WAY, SARASOTA, FL 34242 - $16,000/month (Rental)

  • Located in SARASOTA
  • Built in 1987
  • MLS® #: A4584574
  • 3 Bedrooms
  • 3 Full Baths
  • 1,620 SqFt
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5239 WINDING WAY, SARASOTA, FL 34242 - $1,324,900

  • Located in SARASOTA
  • Built in 1958
  • MLS® #: A4590359
  • 3 Bedrooms
  • 2 Full Baths
  • 1,512 SqFt
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5202 WINDING WAY, SARASOTA, FL 34242 - $1,695,000

  • Located in SARASOTA
  • Built in 2023
  • MLS® #: A4562450
  • 3 Bedrooms
  • 3 Full Baths
  • 2,246 SqFt
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Last Updated Dec, 07 2023
Last Updated: Dec, 07 2023 02:43 pm


Twin Oak Pond, is close to Glebe Park and a short walk to Siesta Key Village where you can enjoy shops, restaurants, or evening drinks.

This quiet neighborhood is casual and relaxed surrounded by tropical vegetation and native habitat. The incredible foliage shuts out noise and maintains a tranquil feeling throughout.

Twin Oak Pond is just 1 mile to Siesta Key’s famous powdery white sands.

Enjoy a bit of the old Florida vibe, in the beach town of Siesta Key, Florida.