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$795,000 Just Listed

  • For Sale
  • Active
  • Condo
  • 2 Beds
  • 2 Full Baths
  • 2,039 Sq. Ft.
  • Updated 1 hour ago
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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, multi-level 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. The breakfast bar connects seamlessly to the dining area and main living space, making it easy to stay connected. There's also a separate family room that offers a more casual spot to unwind. 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 water views. The bathroom is spacious, featuring dual vanities, a soaking 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.

Full Property Details for 3466 Winding Oaks Dr #35

General

  • Price: $795,000
  • HOA FEE: $2,228/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $4,918 (2025)
  • Status: Active
  • Type: Condo
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4686581
  • Updated: Today (4/7/2026)
  • Added to Site: Today

Rental Information

  • Min. Lease: 3 Months

Interior

  • Number of Rooms: 7
  • 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
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
  • Furnishings: Negotiable
  • Flooring: Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared Amenities: Pool
  • Pool Description: Heated, In Ground

Exterior

  • Exterior Features: Irrigation System, Lighting, Sidewalk, Sliding Doors, Storage
  • Deck/Patio: Covered, Deck, Rear Porch
  • Porch/Patio/Deck: Covered, Deck, Rear Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway, Garage Door Opener

Location

  • Area: 34228 - Longboat Key
  • County: Sarasota
  • Development Name: 34228 - Longboat Key
  • Subdivision: WINDING OAKS
  • 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.
  • Direction Faces: East

Community

  • Community Name: 34228 - Longboat Key
  • Community Features: Deed Restrictions, Pool
  • Optional Amenities: Pool
  • Assoc. Name: Fairway Bay Homeowners Association
  • Assoc. Fees Include: Community Pool, Escrow Reserves Fund, Insurance, Maintenance Structure, Maintenance Grounds, Pest Control, Pool Maintenance, Private Road, Sewer, Trash, Water
  • Number of Pets: 2
  • Pet Restrictions: See Documents, / 100lbs.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Connected, Public, Sewer Connected, Underground Utilities, Water Connected

Structural Information

  • Architectural Info: Other
  • Architectural Style: Other
  • Exterior Const.: Block, Stucco
  • Roof: Other
  • Stories/Levels: One
  • Square Feet: 2,039
  • Sq. Ft. Source: Public Records
  • Year Built: 1988

Lot Features

  • Property View: Water
  • Lot Size (Acres): 13.84
  • Lot Size (Sq. Ft.): 602,945
  • Lot Size: 13.8417
  • Street/Road Desc.: Paved

Water Features

  • Water View: Yes

Financial Considerations

  • Condo Fee: $6,684
  • Condo Fee Freq: Quarterly
  • Tax Amount: $4,918.69
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: UNIT 35 WINDING OAKS
  • Flood Zone Info: AE*
  • APN: 4121035
  • Property ID: 4121035
Buyer's Brokerage Compensation: Contact Listing Agent
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— 3466 Winding Oaks Dr #35 —

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NMLS#: 1598647

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Schools serving 3466 Winding Oaks Dr #35

School District:Sarasota County School District
NameGradesDistance
Southside Elementary School, Sarasota, FL
1901 Webber Street, Sarasota, FL 34239
PK-57.3 mi
Booker Middle School
2250 Myrtle Street, Sarasota, FL 34234
6-86.1 mi
Booker High School
3201 North Orange Avenue, Sarasota, FL 34234
9-125.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 3466 Winding Oaks Dr #35 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/07/2026
Listed
$795,000
89.29%
MLS
6/24/2013
Sold
$420,000
—
Public Record
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Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 3466 Winding Oaks Dr #35

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,726
-2%
$405,343
3%
2024
$4,798
2%
$393,919
3%
2023
$4,695
—
$382,446
6%
2021
$4,673
1%
$360,492
-3%
2022
$4,606
-1%
$371,307
12%
2021
$4,673
11%
$330,959
2%
2019
$4,215
2%
$323,518
2%
2018
$4,142
1%
$317,486
2%
2017
$4,116
—
$310,956
2%
2016
$4,098
3%
$304,560
1%
2015
$3,978
—
$302,443
1%
2014
$3,972
-25%
$300,043
-15%
2013
$5,274
—
$351,600
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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3466 Winding Oaks Drive #35, Longboat Key, FL 34228 (MLS# A4686581) is a Condo property with 2 bedrooms and 2 full bathrooms. 3466 Winding Oaks Drive #35 is currently listed for $795,000 and was received on April 07, 2026. This property is listed by Bruce Myer Group from our Longboat Key Office.Want to learn more about 3466 Winding Oaks Drive #35? Do you have questions about finding other Condo real estate for sale in Longboat Key? You can browse all Longboat Key real estate or contact a Coldwell Banker agent to request more information.

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