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$850,000
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Property Description
Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger. Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances. Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops. Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets. Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard. Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association. Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armand's and Downtown Sarasota.
Full Property Details
Full Property Details for 3435 Winding Oaks Dr #18
General
- Sold For: $850,000
- HOA FEE: $2,090/month
- HOA FEE FREQ.: Quarterly
- Taxes: $8,564 (2025)
- Status: Closed
- Type: Condo
- Source: MidFloridaRegionalMLS
- MLS ID: A4680403
- Added to Site: 231 day(s) ago
Rental Information
- Min. Lease: 3 Months
Interior
- Number of Rooms: 10
- Interior Features: Ceiling Fan(s), Eating Space In Kitchen, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Tray Ceiling(s)
- Fireplace: Yes
- Fireplace(s): Living Room
- Appliances: Built-In Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
- Furnishings: Furnished
- Flooring: Carpet, Tile, Vinyl, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Shared Amenities: Pool, Vehicle Restrictions
- Security/Safety: Gated Community, Security Gate, Security System, Security System Leased, Smoke Detector(s)
Exterior
- Exterior Features: Awning(s), Courtyard, Garden, Lighting, Private Entrance, Private Yard, Sliding Doors
- Deck/Patio: Patio, Rear Porch, Screened
- Porch/Patio/Deck: Patio, Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Garage Door Opener
Location
- Area: 34228 - Longboat Key
- County: Sarasota
- Development Name: 34228 - Longboat Key
- Subdivision: WINDING OAKS
- Driving Directions: Gulf Of Mexico Dr to Bay Isle Parkway. Check in at Guard Gate and receive pass. Left on Harbourside drive stay in left lane use pass to continue through manual gate. Take right on Winding Oaks Drive Villa is 9th on the right hand side.
- Direction Faces: Southwest
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, Association Recreation - Owned, Buyer Approval Required, Deed Restrictions, Gated Community - Guard, Pool
- Optional Amenities: Pool, Vehicle Restrictions
- Association: Yes
- Assoc. Name: Neil Fleet
- Assoc. Fees Include: 24-Hour Guard, Cable TV, Common Area Taxes, Community Pool, Escrow Reserves Fund, Fidelity Bond, Maintenance Structure, Maintenance Grounds, Pool Maintenance, Recreational Facilities, Trash
- Number of Pets: 2
- Pet Restrictions: 100lbs.
Heating & Cooling
- Cooling Type: Central Air, Humidity Control
- Heating Type: Central, Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Public, Sewer Connected, Underground Utilities, Water Connected
Structural Information
- Exterior Const.: HardiPlank Type
- Roof: Tile
- Common Walls: Corner Unit
- Windows: Blinds, Window Treatments
- Stories/Levels: One
- Square Feet: 2,555
- Sq. Ft. Source: Public Records
- Living Area: 2,555 Sq. Ft.
- Year Built: 1988
Lot Features
- Property View: Golf Course, Water
- Lot Size (Acres): 13.84
- Lot Size (Sq. Ft.): 602,945
- Lot Size: 13.8417
- Street/Road Desc.: Asphalt
- Fencing (Description): Masonry
Water Features
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Bay/Harbor, Beach, Gulf/Ocean, Pond
- Water Front Desc.: Gulf/Ocean Front
Financial Considerations
- Assoc Fee Desc.: None
- Condo Fee: $6,271
- Condo Fee Freq: Quarterly
- Tax Amount: $8,564.88
- Tax Year: 2025
Disclosures and Reports
- Ownership: Condominium
- Special Conditions: None
- Legal Description: UNIT 18 WINDING OAKS
- Flood Zone Info: AE
- APN: 4121018
- Property ID: 4121018
Listed and Sold by Michael Saunders & Company
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Schools
Schools serving 3435 Winding Oaks Dr #18
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 |
Booker High School 3201 North Orange Avenue, Sarasota, FL 34234 | 9-12 | 5.1 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 3435 Winding Oaks Dr #18
Date
Details
Price
Change
Source
9/03/2026
Sold
$850,000
-10.43%
MLS
5/20/2026
Price Reduced
$949,000
-9.62%
MLS
3/24/2026
Price Reduced
$1,050,000
-8.7%
MLS
2/26/2026
Listed
$1,150,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
3435 Winding Oaks Drive #18, Longboat Key, FL 34228 (MLS# A4680403) is a Condo property that was sold at $850,000 on September 03, 2026. Want to learn more about 3435 Winding Oaks Drive #18? 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.

