$949,000
3435 Winding Oaks Drive
Longboat Key, FL 34228
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history96 days on market
- Status: ActiveFeb 26, 2026
- Listed$1,150,000Feb 26, 2026
- Price reduced$949,000
Facts & features
- Property type
- Residential
- Sub type
- Condominium
- Status
- Active
- Days on market
- 96
- Subdivision
- Winding Oaks
- County
- Sarasota
- Year built
- 1988
- Living area
- 2,555 sq ft
- Price/sq ft
- $371
- Building area
- 3,270 sq ft (Public Records)
- Lot size
- 602,945 sq ft
- Lot category
- 10 to less than 20
- Flood zone
- AE
- Garage
- 2 spaces
- Annual taxes
- $8,565 (2025)
- Parcel #
- 0004121018
- Zoning
- MUC1
- MLS #
- A4680403
Interior Details
- Bedrooms
- 3
- Full bathrooms
- 2
- Half bathrooms
- 1
- Flooring
- Carpet, Tile, Vinyl, Wood
- Appliances
- Built-In Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
- Interior features
- Ceiling Fans(s), Eat-in Kitchen, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Tray Ceiling(s)
- Laundry
- Inside, Laundry Room
- Stories / Levels
- One
- Direction faces
- Southwest
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central, Electric
- Cooling
- Central Air, Humidity Control
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Garage Door Opener
HOA & Financial
- Total monthly fees
- $2,167/mo
- Total annual fees
- $26,006
- HOA name
- Neil Fleet
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 3 Months
- Listing terms
- Cash, Conventional
- Ownership
- Condominium
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- See Rules
- Approval process
- See Rules
Exterior & Construction
- Exterior features
- Awning(s), Courtyard, Garden, Lighting, Private Entrance, Private Yard, Sliding Doors
- Construction materials
- HardiPlank Type
- Roof
- Tile
- Foundation
- Block, Slab
- Water access
- Yes
- Water view
- Yes
- Road surface
- Asphalt
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- BB/HS Internet Available, Cable Available, Electricity Connected, Public, Sewer Connected, Underground Utilities, Water Connected
Community
- Pets allowed
- Dogs OK, Size Limit, Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Primary Bedroom | First | 18x14 |
| Living Room | First | 16x19 |
| Dining Room | First | 11x19 |
| Kitchen | First | 11x15 |
| Bathroom 1 | First | 12x10 |
| Bedroom 2 | First | 13x13 |
| Bathroom 2 | First | 5x5 |
| Den | First | 12x14 |
| Laundry | First | 5x10 |
| Office | First | 18x7 |
Listing Details
- Listing date
- 2026-01-28
- On market date
- 2026-02-26
- Original list price
- $1,150,000
- Occupant type
- Owner
- MLS area
- 34228 - Longboat Key
- Listing AOR
- Sarasota - Manatee
- Status changed
- 2026-02-26
- Tax legal description
- UNIT 18 WINDING OAKS
Flood risk
FEMA Special Flood Hazard Area (1% annual-chance / “100-year” floodplain). Flood insurance is generally required by mortgage lenders.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively 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.
Based on information submitted to the MLS GRID as of June 2, 2026 at 10:40 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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