3466 WINDING OAKS DRIVE 35 Longboat Key, FL $ 795,000
3466 WINDING OAKS DRIVE 35
$ 795,000
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3466 WINDING OAKS DRIVE 35

Longboat Key, FL, 34228
$ 795,000
Bedrooms2 Baths2.0 Sq 2,039

Monthly Estimate*

$ 4,895

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View a Virtual Tour

Condo for sale in Longboat Key, FL

for $795,000 with 2 bedrooms and 2 full baths. This 2,039 square foot condo was built in 1988 on a lot size of 13.84.

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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Condo Active

Price

$ 795,000

Bedrooms

2

Full Bath

2

Property Type

Condo

Taxes

$ 4,918

Style

Other

Lot Size

13.84

Year Built

1988

Town/City

Longboat Key

County/Region

Manatee

MLS | Web ID

A4686581

Features
General
Sewer Public Sewer
Heating Central Electric
Cooling Central Air
Utilities Electricity Connected Public Sewer Connected Underground Utilities Water Connected
Roof Other
Appliances Built-In Oven Cooktop Dishwasher Disposal Dryer Microwave Refrigerator Washer
Zoning MUC1
Garage Spaces 2
Association Fee Includes Community Pool Escrow Reserves Fund Insurance Maintenance Structure Maintenance Grounds Pest Control Pool Maintenance Private Road Sewer Trash Water
Patio/Porch Features Covered Deck Rear Porch
Architectural Style Other
Pool Features Heated In Ground
Construction Materials Block Stucco
Pets Allowed Yes
Year Built 1988
View Water
Levels One
Unit Number 35
Property Subtype Condominium
Tax Year 2025
Ownership Fee Simple
Community Features Deed Restrictions Pool
HOA Fee 2 791.03
County Sarasota
New Construction false
Property Type Residential
Association Amenities Pool
Attached Garage true
Subdivision Name WINDING OAKS
Facing Direction East
Garage Y/N true
Total Rooms 7
Full Baths 2
Status Active
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.
City LONGBOAT KEY
Association Name Advanced Management / AMIA
Senior Community Y/N false
MLS Area 34228 - Longboat Key
Lot Size Units Acres
Lot Size Square Feet 602945
Carport Y/N false
Listing Terms Cash Conventional
HOA Fee 2 Frequency Annually
Land Lease Y/N false
Tax Annual Amount 4918.69
Home Warranty Y/N false
Property Condition Completed
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://listing.noblesandheroes.com/ut/3466_Winding_Oaks_Dr_35.html
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 0
Legal Description UNIT 35 WINDING OAKS
Pet Size Limit Large (61-100 Lbs.)
Minimum Lease 3 Months
Water Access Y/N false
Monthly Condo Fee Amount 2228
HOA Monthly Maintenance 0
Water View Y/N false
Flood Zone Code AE*
DockY/N false
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Interior
Interior Amenities Built-in Features Ceiling Fan(s) Eating Space In Kitchen Open Floorplan Primary Bedroom Main Floor Solid Surface Counters Stone Counters Thermostat Window Treatments
Flooring Tile Hardwood
Furnished Y/N Negotiable
Total Stories 1
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N false
Half Baths 0
Laundry Features Laundry Room
Total Bedrooms 2
Total Baths 2
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Exterior
Exterior Amenities Irrigation System Lighting Sidewalk Sliding Doors Storage
Vegetation Mature Landscaping
Parking Features Driveway Garage Door Opener
Water Source Public
Lot Size Area 13.8417
Foundation Details Slab
Building Area Total 2568
Lot Size Acres 13.84
Road Surface Type Paved
Private Pool false
Waterfront Y/N false
Covered Spaces 2
Road Responsibility Private Maintained Road
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* Excluded Features
List By
Coldwell Banker Realty

Broker

bruce@brucemyer.com

Email

Affordability Calculator

$5,305
Per Month
92%
8%
0%
Monthly Principal & Interest
$4,895
Monthly Property Taxes
$410
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4827338 Elementary School
4827337 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
4/7/2026$795,000 Listed Price

Map


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3466 WINDING OAKS DRIVE 35, Longboat Key, FL, 34228 is a Condo for sale at $795,000 with 2,039 sqft and a lot size of 13.84. 3466 WINDING OAKS DRIVE 35 has 2 bedrooms, 2.0 baths, and was built in 1988. The property's zip code is 34228 which is in Longboat Key, FL