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$795,000

3466 Winding Oaks Drive Longboat Key, FL 34228 Residential - Condominium Active

  • 3466 Winding Oaks Drive, Unit 35, Longboat Key, FL 34228 Main Photo

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Description

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 Highlights

Property Type: Residential - Condominium
Cooling: Central Air
Garage: 2 car attached
Heating: Central, Electric
Lot Size: 13.84 Acres
Roof Type: Other
Stories: 1.0
Taxes: $4,918
Year Built: 1988

General Information

Bedrooms: 2
Bathrooms: 2 Full
Sqft: 2,039
County: Sarasota
Subdivision: WINDING OAKS
Listed By:
Bruce Myer COLDWELL BANKER REALTY 941-383-6411

Amenities

Built-in Features
Ceiling Fans(s)
Eat-in Kitchen
Open Floorplan
Primary Bedroom Main Floor
Solid Surface Counters
Stone Counters
Thermostat
Window Treatments
Lighting
Sidewalk
Sliding Doors
Storage

Room Information

Living Room: 15x19
Kitchen: 17x11
Balcony/Porch/Lanai: 35x16
Dining Room: 12x12
Primary Bedroom: 15x16
Bedroom 2: 15x14
Family Room: 16x13

Property Features

Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
Association Amenities: Pool
Community Features: Deed Restrictions, Pool
Condo Fee: $6684/ Quarterly
Days on Site: 4
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.
Exterior: Block, Stucco
Flood Zone Code: AE*
Flooring: Tile, Wood
Foundation: Slab
Home Warranty Y/N: No
Listing Terms: Cash, Conventional
Lot Dimensions: 13.84
Number of Pets: 2
Other Equipment: Irrigation Equipment
Ownership: Fee Simple
Parking: Driveway, Garage Door Opener
Parking Notes: Driveway, Garage Door Opener
Patio/Porch: Covered, Deck, Rear Porch
Pets Allowed: Yes
Pets Restrictions: See Documents
Pets Size: Large (61-100 Lbs.)
Pets Weight (Max): 100
Pool: Heated, In Ground
Property Attached Y/N: No
Property Sub-Type: Condominium
Sewer: Public Sewer
Showing Instructions: Listing Agent Must Accompany, ShowingTime
Special Sale Provisions: None
Utilities: Electricity Connected, Public, Sewer Connected, Underground Utilities, Water Connected
Vegetation: Mature Landscaping
Water: Public
Water Access Y/N: No
Zoning: MUC1
$795,000
2beds
2.0baths
2,039sqft
2cars
New to the Market Active
BEDS2 BATHS2 full SQUARE FEET2,039 MLS#A4686581
STATUSActive PROPERTY TYPEResidential - Condominium SUBDIVISIONWINDING OAKS

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3466 Winding Oaks Drive, Unit 35, Longboat Key, FL 34228.

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Estimated Payment

$ 3,323.11 per month $2,681.40 Principal & Interest $409.83 Property Tax $231.88 Homeowner's Insurance

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About this area

Florida/Longboat Key
Longboat Key

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About Longboat Key

Longboat Key, FL recently was named one of Condé Nast's Top Ten Traveler’s Islands. Longboat Key possesses something uniquely its own. There is a natural beauty and elegance to Longboat Key that entrances visitors and residents, and in many ways it’s the perfect beach getaway. Those that live there have stunning scenery, a luxurious vibe, and easy access to places like Sarasota, Bradenton, and Tampa.


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About this community

Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/11/2026. The listing information on this page last changed on 04/11/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 04/11/2026 12:47:06 AM EST) or Stellar MLS (last updated Sat 04/11/2026 12:29:13 AM EST). Real estate listings held by brokerage firms other than Wagner Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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