Located in one of the most sought-after villa communities on

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Condo For Sale

3466 WINDING OAKS DR 35

Longboat Key, Florida 34228

Sarasota County

Community: WINDING OAKS

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$795,000 2 br, 2.0 bath 2039 sq. ft. 13.840 acres

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.

Interior:
  • Bedrooms: 2
  • Baths: 2.0
  • Sq Ft: 2039
  • Year Built: 1988
  • Utilities: 
  • Fireplaces: 
  • Stories: 
  • Heat/AC: Central, Electric (Heating)
  • Garage: Driveway, Garage, Garage - Attached
Exterior:
  • Lot Size: 13.840 acre
  • Lot Dimensions: 
  • View Types: 
  • Yard: 
  • Siding: Block, Stucco
  • Roof: 
  • Property Taxes: $4,919
  • MLS #: A4686581
  • Unit Number: 35
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Contact Information:
Beach Condo For Sale in Longboat Key, Florida
Listing Agent: Bruce Myer, Coldwell Banker, 941-376-5311, 941-383-6411 Listing Site, Listing Status: Active
Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Ad Number: 7530784
Viewed 23 times.
Updated: Apr 07, 2026

This property is a Condo located at 3466 WINDING OAKS DR 35, Longboat Key, Florida 34228, and is currently For Sale at $795,000. This Condo has 2 bedrooms, 2.0 baths, 2039 sq ft.