$1,150,000
3427 Winding Oaks Drive
Longboat Key, FL 34228
Property type
Year built
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
Under contract-accepting backup offers. Privately tucked away within the private Winding Oaks community on Longboat Key, this beautifully updated three-bedroom villa offers an easy, elevated way to enjoy Sarasota’s coastal lifestyle. Overlooking the Harbourside Golf Course, the home captures peaceful water views and the scenic 5th hole, creating a backdrop that feels both open and serene. Designed for effortless living, this turnkey furnished residence blends the comfort of a single-family home with the simplicity of maintenance-free ownership—ideal for seasonal stays or extended escapes. Inside, an airy open layout, soaring ceilings, and wide-plank tile floors create a light, welcoming feel, while floor-to-ceiling sliders connect seamlessly to the outdoor living spaces. The kitchen is both stylish and functional, featuring Italian white-lacquer cabinetry, stone countertops, and premium appliances—perfect for casual evenings at home or hosting friends. The living room centers around a custom gas fireplace and flows naturally to a spacious screened lanai, where you can unwind with long water views and soft coastal breezes. The home features many new furnishings and many recent updates. A private courtyard with a heated pool adds another layer of relaxation, offering a quiet place to start the day or wind down after time on the water, golf course or tennis courts. The primary suite is a calm retreat of its own, with tranquil water views, a spa-like bath, and a generous walk-in closet. Two additional en-suite bedrooms provide flexibility for visiting guests or a comfortable home office. Ownership includes access to the Bay Isles Beach Club, where days can be spent on pristine Gulf-front sands with thoughtfully appointed amenities. Within Winding Oaks, residents enjoy a recently refreshed community pool, walking paths, and a secure, gated setting. Optional golf, tennis and social memberships are available at the Longboat Key Club. Just minutes from dining and shopping on world-renowned St. Armands Circle and the cultural amenities of downtown Sarasota, this retreat makes it easy to step into the best of the area—while always having a peaceful place to return to. Simple, sophisticated, and distinctly Longboat Key.
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 history36 days on market
- Status: PendingJun 1, 2026
- Listed$1,150,000Mar 23, 2026
- Price increased$1,150,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Condominium
- Status
- Pending
- Days on market
- 36
- Subdivision
- Winding Oaks
- County
- Sarasota
- Year built
- 1988
- Living area
- 2,555 sq ft
- Price/sq ft
- $450
- Building area
- 3,270 sq ft (Public Records)
- Lot size
- 0 sq ft
- Lot category
- Non-Applicable
- Flood zone
- AE, X
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $13,850 (2025)
- Parcel #
- 0004121014
- Zoning
- MUC1
- MLS #
- A4686623
Interior Details
- Bedrooms
- 3
- Full bathrooms
- 3
- Flooring
- Luxury Vinyl, Tile
- Appliances
- Built-In Oven, Cooktop, Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer, Wine Refrigerator
- Interior features
- Built-in Features, Ceiling Fans(s), Eat-in Kitchen, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments
- Laundry
- Inside, Laundry Room
- Stories / Levels
- One
- Direction faces
- West
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central, Electric, Natural Gas
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Deeded, Driveway, Garage Door Opener
HOA & Financial
- Total monthly fees
- $2,398/mo
- Total annual fees
- $28,776
- HOA name
- Winding Oaks/Neil Fleet
- CDD
- No
- Min lease term
- 3 Months
- Listing terms
- Cash, Conventional, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- See Documents
- Approval process
- See Documents
Exterior & Construction
- Exterior features
- Awning(s), Lighting, Sliding Doors
- Construction materials
- HardiPlank Type
- Roof
- Tile
- Foundation
- Slab
- Pool
- Private pool
- Waterfront
- Yes
- Water access
- Yes
- Water view
- Yes
- Road surface
- Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Electricity Connected, Natural Gas Available, Sewer Connected, Underground Utilities, Water Connected
Community
- Pets allowed
- Cats OK, Dogs OK, Number 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 |
|---|---|---|
| Balcony/Porch/Lanai | First | 29x46 |
| Primary Bedroom | First | 20x15 |
| Bedroom 2 | First | 14x14 |
| Bedroom 3 | First | 12x15 |
| Kitchen | First | 19x31 |
| Living Room | First | 15x19 |
| Dining Room | First | 13x21 |
| Balcony/Porch/Lanai | First | 10x10 |
| Balcony/Porch/Lanai | First | 11x15 |
| Laundry | First | 5x11 |
Listing Details
- Listing date
- 2026-03-23
- On market date
- 2026-03-23
- Original list price
- $1,150,000
- Occupant type
- Vacant
- MLS area
- 34228 - Longboat Key
- Listing AOR
- Sarasota - Manatee
- Status changed
- 2026-06-01
- Tax legal description
- UNIT 14 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
North on Gulf of Mexico Drive to the light at Bay Isles Parkway. Turn right into Bay Isles, go to gatehouse, continue on Harbourside Drive to Winding Oaks on right.
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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 1, 2026 at 12:08 PM 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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