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3466 WINDING OAKS DRIVE #35, LONGBOAT KEY, FL
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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Property Type
Condo
Style
Other
Year Built
1988
Lot Size
13.84 acres
Price / Sqft
$390
Days on Market
1 days
Full Baths
2
Subdivision
WINDING OAKS
HOA
None
MLS #
MFR784983883
Listing Type
Residential
Market
MFRMLS
3466 WINDING OAKS DRIVE #35, LONGBOAT KEY, FL 34228 — Sarasota County
Bruce Myer
COLDWELL BANKER REALTY

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How this home compares across city, state, and national benchmarks
Listed at $795,000, this 2-bed condo in LONGBOAT KEY is 17% below the Census median home value of $959,200 for LONGBOAT KEY. Compared to 22 other 2-bed homes in LONGBOAT KEY (averaging $874,864), this property is 9% below average. Florida's median home value is $299,867, putting this listing 165% above the state benchmark. The U.S. national median home value is $334,900.
Where this listing falls among 41 homes for sale
Standout Features
Above Average
Standard
LONGBOAT KEY has a population of 7,512 with a median household income of $143,365 and a homeownership rate of 93.6%. The median home value is $959,200 and the median rent is $2,969/mo.
Sources: U.S. Census Bureau ACS 2023, Fizbo listing data