$795,000
Off-Market Date: 05/20/20263466 Winding Oaks Drive #35 Longboat Key, FL 34228
Pending MLS# A4686581
2 beds 2 baths 2,039 sq ft Condo
Details for 3466 Winding Oaks Drive #35
MLS# A4686581
Description for 3466 Winding Oaks Drive #35, Longboat Key, FL, 34228
Under contract-accepting backup offers. 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.
Listing Information
Property Type: Residential, Condominium
Status: Pending
Bedrooms: 2
Bathrooms: 2
Lot Size: 13.84 Acres
Square Feet: 2,039 sq ft
Year Built: 1988
Garage: Yes
Stories: 1 Story
Construction: Block,Stucco
Construction Display: New Construction
Subdivision: Winding Oaks
Foundation: Slab
County: Sarasota
Construction Status: New Construction
Room Information
Main Floor
Family Room: 13x16
Bedroom 2: 14x15
Primary Bedroom: 16x15
Dining Room: 12x12
Porch: 16x35
Kitchen: 11x17
Living Room: 19x15
Bathrooms
Full Baths: 2
Additonal Room Information
Laundry: Laundry Room
Interior Features
Appliances: Built-In Oven, Refrigerator, Microwave, Washer, Cooktop, Dishwasher, Disposal, Dryer
Flooring: Tile,Wood
Doors/Windows: Window Treatments
Additional Interior Features: Eat-In Kitchen, Window Treatments, Ceiling Fan(s), Open Floorplan, Built-in Features, Solid Surface Counters, Stone Counters, Main Level Primary
Utilities
Water: Public
Sewer: Public Sewer
Other Utilities: Electricity Connected,Municipal Utilities,Sewer Connected,Underground Utilities,Water Connected
Cooling: Ceiling Fan(s), Central Air
Heating: Central, Electric
Exterior / Lot Features
Attached Garage: Attached Garage
Garage Spaces: 2
Parking Description: Garage, driveway, Garage Door Opener
Roof: Other
Pool: Heated, Association, Community, In Ground
Lot View: Water
Additional Exterior/Lot Features: Sprinkler/Irrigation, Lighting, Storage, Covered, Deck, Rear Porch, Landscaped
Community Features
Community Features: Pool, Sidewalks
Association Amenities: Pool
HOA Dues Include: Water, Trash, Insurance, Maintenance Grounds, Pest Control, Sewer, Reserve Fund, Road Maintenance, Maintenance Structure, Pool(s)
Driving Directions
From St. Armands Circle - North to Gulf of Mexico Dr, turn right at south gate for Bay Isles (Harbourside Dr), turn right to 2020 Harbourside Dr.
Financial Considerations
Terms: Cash,Conventional
Tax/Property ID: 0004121035
Tax Amount: 4918.69
Tax Year: 2025
A broker reciprocity listing courtesy: COLDWELL BANKER REALTY
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Sales History & Tax Summary for 3466 Winding Oaks Drive #35
Sales History
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Tax Summary
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
Schools
Schools nearby 3466 Winding Oaks Drive #35
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The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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