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3466 Winding Oaks Drive, Unit 35Longboat Key, FL 34228Price: $795,000

  • Price: $795,000
  • Est. Mortgage of $/month
  • 43 Days on Market
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Federal 30-year interest rate: 6.36% last updated on May 14, 2026
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  • $795,000List Price
  • ActiveStatus
  • 50Number of Photos
  • 27.377941Latitude
  • 3466 Winding Oaks DriveAddress
  • Winding Oaks DriveStreet
  • 35Unit Number
  • Longboat KeyTown
  • FLState
  • 34228Zip
  • SarasotaCounty
  • ResidentialProperty Type
  • A4686581MLS Number
  • 2Bedrooms
  • 2Full Bath
  • 2,039Square Feet
  • 1988Year Built
  • 13.84Acreage

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Located in one of the most sought-after villa communities on Longboat Key, this well-kept 2-bedroom, 2-bath home in Winding Oaks lives more like a single-family residence-without all the upkeep. Behind the gates of Bay Isles, it offers a great opportunity to enjoy a quiet, established neighborhood known for its natural beauty and relaxed feel. A paver driveway and walkway, surrounded by mature landscaping, lead you to the front door. Inside, high ceilings and warm wood floors immediately make the space feel open and inviting. The finishes are neutral and timeless, and the natural light really does the rest. Impact glass throughout adds both comfort and peace of mind. The main living area flows easily, with a striking corner of sliding glass doors that brings the outdoors in and opens to a spacious, screened, deck. It's the kind of space you'll actually use-whether that's for entertaining, relaxing, or just enjoying the greenery around you. The kitchen is nicely laid out with stone countertops, stainless appliances, a tray ceiling, and a large window that keeps things bright. Both bedrooms are generously sized. The primary suite feels like a true retreat, with vaulted ceilings, a walk-in closet, and sliding doors that open to the deck with peaceful nature views. The bathroom is spacious, featuring dual vanities, a Jacuzzi tub, walk-in shower, and well-done tile details. Additional highlights include a two-car garage and a floor plan that offers a nice balance of openness and privacy. Winding Oaks is part of the Bay Isles Harbourside golf course community and offers a gated entrance, community pool, and access to Bay Isles amenities-including deeded beach access through the private Bay Isles Beach Club. It's an easy, comfortable lifestyle in one of Longboat Key's most desirable communities.

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LISTING COURTESY OF Bruce Myer of COLDWELL BANKER REALTY (941-383-6411)

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of May 20, 2026 8:04 AM EDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

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Property Details of 3466 Winding Oaks Drive, Unit 35

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