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$900,000
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Property Description
This stunning three-bedroom, three-bath villa offers a serene waterfront retreat in the desirable Winding Oaks community of Longboat Key Club. With a spacious open floor plan spanning 2,608 Sf, the maintenance-free home is bathed in natural light and features vaulted ceilings that enhance its airy feel. The inviting living/dining room combo seamlessly connects to a screened-in back deck, perfect for enjoying picturesque water views. The kitchen is a chef's dream, equipped with a gas range, large refrigerator with ice maker, built-in oven, custom wood cabinetry, and ample counter space for culinary creations. A cozy den adjacent to the kitchen provides a perfect gathering spot for family and friends. The thoughtfully designed layout ensures privacy among the three bedrooms, with one versatile space featuring a Murphy bed ideal for an office or guest room. Residents enjoy exclusive access to the Bay Isles Beach Club and 24-hour security, all while being conveniently located near shopping, dining, and the luxurious St. Regis Longboat Key Resort. Importantly, the villa at Winding Oaks has proven resilient, having not sustained any damage from recent hurricanes.
Full Property Details
Full Property Details for 3465 Winding Oaks Dr #33
General
- Sold For: $900,000
- HOA FEE: $2,090/month
- HOA FEE FREQ.: Quarterly
- Taxes: $7,137 (2024)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: A4670325
- Added to Site: 79 day(s) ago
Rental Information
- Min. Lease: 3 Months
Interior
- Number of Rooms: 5
- Interior Features: Ceiling Fan(s), High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
- Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Range, Refrigerator, Washer
- Furnishings: Furnished
- Flooring: Carpet, Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Electric Dryer Hookup, Laundry Room, Washer Hookup
Additional Information
- Shared Amenities: Gated, Recreation Facilities, Security, Vehicle Restrictions
- Security/Safety: Gated Community, Smoke Detector(s)
Exterior
- Exterior Features: Awning(s), Courtyard, Garden, Irrigation System, Lighting, Private Mailbox, Sliding Doors
- Deck/Patio: Deck, Screened
- Porch/Patio/Deck: Deck, Screened
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: North on Gulf of Mexico Drive to Bay Isles Parkway, turn right onto Bay Isles Pkwy, go to security gate and ask for code to get in second gate. Turn left onto Harbourside Dr., go through second gate and take 2nd right onto Winding Oaks Drive. 3465 WO is second villa on the left.
- Direction Faces: West
School Information
- Elementary School: Southside Elementary
- Middle School: Booker Middle
- High School: Booker High
Community
- Community Name: 34228 - Longboat Key
- Community Features: Gulf/Ocean Front, Water Access, Association Recreation - Owned, Buyer Approval Required, Deed Restrictions, Pool, Special Community Restrictions
- Optional Amenities: Gated, Recreation Facilities, Security, Vehicle Restrictions
- Assoc. Name: Bay Isles/Neil Fleet
- Assoc. Fees Include: 24-Hour Guard, Cable TV, Community Pool, Escrow Reserves Fund, Insurance, Maintenance Structure, Maintenance Grounds, Maintenance Repairs, Manager, Pest Control, Pool Maintenance, Private Road, Trash
- Number of Pets: 2
- Pet Restrictions: See documents., / 100lbs.
Heating & Cooling
- Cooling Type: Central Air, Zoned
- Heating Type: Central, Electric, Zoned
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable TV Available, Natural Gas Connected, Sewer Connected, Underground Utilities, Water Connected
Structural Information
- Exterior Const.: HardiPlank Type
- Roof: Tile
- Windows: Blinds
- Stories/Levels: One
- Square Feet: 2,608
- Sq. Ft. Source: Public Records
- Living Area: 2,608 Sq. Ft.
- Year Built: 1988
Lot Features
- Property View: Garden, Trees/Woods, Water
- Frontage: Street Paved, Private Road
- Street/Road Desc.: Paved, Asphalt
Water Features
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Gulf/Ocean
- Water Front Desc.: Gulf/Ocean Front
Financial Considerations
- Condo Fee: $6,271
- Condo Fee Freq: Quarterly
- Tax Amount: $7,137.02
- Tax Year: 2024
Disclosures and Reports
- Ownership: Condominium
- Special Conditions: None
- Legal Description: UNIT 33 WINDING OAKS
- Flood Zone Info: AE
- APN: 4121033
- Property ID: 4121033
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Schools
Schools serving 3465 Winding Oaks Dr #33
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Southside Elementary School, Sarasota, FL 1901 Webber Street, Sarasota, FL 34239 | PK-5 | 7.3 mi |
Booker Middle School 2250 Myrtle Street, Sarasota, FL 34234 | 6-8 | 6.1 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 3465 Winding Oaks Dr #33
Date
Details
Price
Change
Source
11/14/2025
Sold
$900,000
0.56%
MLS
10/30/2025
Listed
$895,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
3465 Winding Oaks Drive #33, Longboat Key, FL 34228 (MLS# A4670325) is a Single Family property that was sold at $900,000 on November 14, 2025. This property was sold by Ryan Heers from our Longboat Key Office.Want to learn more about 3465 Winding Oaks Drive #33? Do you have questions about finding other Single Family 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.


