3466 WINDING OAKS DRIVE UNIT 35 LONGBOAT KEY FL 34228 MLS #A4686581

3466 WINDING OAKS DRIVE UNIT 35
LONGBOAT KEY, FL, 34228
$795,000
2 Beds
2 Baths
2,039 SqFt
13.84 Acres
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MLS #A4686581 image #0
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.

Property Details

Price:
$795,000
MLS #:
A4686581
Status:
Active
Beds:
2
Baths:
2
Type:
Condo
Subtype:
Condominium
Subdivision:
WINDING OAKS
Neighborhood:
34228longboatkey
Listed Date:
Apr 7, 2026
Finished Sq Ft:
2,039
Total Sq Ft:
2,568
Lot Size:
602,945 sqft / 13.84 acres (approx)
Year Built:
1988
OtherPoolPrimary Bedroom Main Floor34228 – Longboat Key34228longboatkeyWinding OaksWaterSee Documents3 MonthsPets Allowed

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Schools

Interior

Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Tile, Hardwood
Heating
Central, Electric
Interior Features
Built-in Features, Ceiling Fan(s), Eating Space In Kitchen, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Stone Counters, Thermostat, Window Treatments
Laundry Features
Laundry Room
Levels
One

Exterior

Architectural Style
Other
Association Amenities
Pool
Attached Garage YN
1
Community Features
Deed Restrictions, Pool
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
East
Exterior Features
Irrigation System, Lighting, Sidewalk, Sliding Doors, Storage
Garage Spaces
2
Open Parking YN
1
Parking Features
Driveway, Garage Door Opener
Patio And Porch Features
Covered, Deck, Rear Porch
Roof
Other
View
Water

Financial

HOA Fee 2
$791
HOA Fee 2 Frequency
Annually
HOA Includes
Community Pool, Escrow Reserves Fund, Insurance, Maintenance Structure, Maintenance Grounds, Pest Control, Pool Maintenance, Private Road, Sewer, Trash, Water
HOA Name
Advanced Management / AMIA
HOA Name 2
Bay Isles Homeowners Association
HOA Phone
941-383-3200
HOA Phone 2
941-383-3200
Tax Year
2025
Taxes
$4,919

Map

Community

Subdivisions in LONGBOAT KEY

Market Summary

Current real estate data for Condo in LONGBOAT KEY as of May 09, 2026
292
Condo Listed
138
Avg DOM
734
Avg $ / SqFt
$1,348,537
Avg List Price

Property Summary

    Located in the WINDING OAKS subdivision, 3466 WINDING OAKS DRIVE UNIT 35 LONGBOAT KEY FL is a Condo for sale in LONGBOAT KEY, FL, 34228. It is listed for $795,000 and features 2 beds, 2 baths, and has approximately 2,039 square feet of living space, and was originally constructed in 1988. The current price per square foot is $390. The average price per square foot for Condo listings in LONGBOAT KEY is $734. The average listing price for Condo in LONGBOAT KEY is $1,348,537. To schedule a showing of MLS#a4686581 at 3466 WINDING OAKS DRIVE UNIT 35 in LONGBOAT KEY, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

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3466 WINDING OAKS DRIVE UNIT 35
LONGBOAT KEY, FL