About 3435 Winding Oaks Drive 18
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.
Features of 3435 Winding Oaks Drive 18
| MLS® # | A4680403 |
|---|---|
| Price | $949,000 |
| Bedrooms | 3 |
| Bathrooms | 3.00 |
| Full Baths | 2 |
| Half Baths | 1 |
| Square Footage | 2,555 |
| Acres | 13.84 |
| Year Built | 1988 |
| Type | Residential |
| Sub-Type | Condominium |
| Status | Pending |
Community Information
| Address | 3435 Winding Oaks Drive 18 |
|---|---|
| Area | Longboat Key |
| Subdivision | WINDING OAKS |
| City | LONGBOAT KEY |
| County | Sarasota |
| State | FL |
| Zip Code | 34228-4131 |
Amenities
| Amenities | Pool, Vehicle Restrictions |
|---|---|
| Parking | Garage Door Opener |
| # of Garages | 2 |
| View | Golf Course, Water |
| Is Waterfront | No |
| Waterfront | Gulf/Ocean Front |
| Has Pool | No |
Interior
| 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) |
|---|---|
| Appliances | Built-In Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer |
| Heating | Central, Electric |
| Cooling | Central Air, Humidity Control |
| Fireplace | Yes |
| Fireplaces | Living Room |
| # of Stories | 1 |
Exterior
| Exterior Features | Awning(s), Courtyard, Garden, Lighting, Private Entrance, Private Yard, Sliding Doors |
|---|---|
| Roof | Tile |
| Foundation | Block, Slab |
School Information
| Elementary | Southside Elementary |
|---|---|
| Middle | Booker Middle |
| High | Booker High |
Additional Information
| Date Listed | February 26th, 2026 |
|---|---|
| Days on Market | 187 |
| Zoning | MUC1 |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Office | MICHAEL SAUNDERS & COMPANY |
|---|