About 5244 Winding Way
Expansive Coastal Modern Property in a Serene and Peaceful Setting, Seconds to Siesta Key Beach ** 4 Bedrooms, 4 Full Baths with Detached Studio/ADU above the 3 Car Garage (5 Total Bedrooms, 5 Bathrooms) ** Gorgeous Pool among Lush Native Landscape ** NEW ROOF! There is no better value on Siesta Key for your primary occupancy or 2nd home with opportunities to cash flow this investment. The entire property has been updated with wood-looking vinyl, interior/exterior paint, custom baseboard and trim, contemporary lighting fixtures, modern fans and fresh marcite in the refinished pool. The studio provides new vinyl windows and a mini-split AC unit for energy efficient climate controlling of this private space. You will love the floor plan of both the main house and studio! The main house provides a great room concept with an abundance of joyful natural light and multiple sets of French doors leading to the pool. Each bedroom receives a private bath with 2 primary suites enjoying idyllic views of the pool and tropical landscape. Simply stated, this estate property is meant for hosting large groups, comfortably. Located inside the charming Canopy Roads of Twin Oak, this beach property is private, serene and inspiring. Live by the beach, but away from the noise. The good life is found here
Features of 5244 Winding Way
| MLS® # | A4669581 |
|---|---|
| Price | $1,250,000 |
| Bedrooms | 4 |
| Bathrooms | 4.00 |
| Full Baths | 4 |
| Square Footage | 2,100 |
| Acres | 0.22 |
| Year Built | 1967 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Status | Active |
Community Information
| Address | 5244 Winding Way |
|---|---|
| Area | Sarasota/Crescent Beach/Siesta Key |
| Subdivision | TWIN OAK POND |
| City | SARASOTA |
| County | Sarasota |
| State | FL |
| Zip Code | 34242-1848 |
Amenities
| # of Garages | 3 |
|---|---|
| Is Waterfront | No |
| Has Pool | Yes |
Interior
| Interior Features | Kitchen/Family Room Combo, Open Floorplan, Solid Surface Counters, Walk-In Closet(s) |
|---|---|
| Appliances | Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer |
| Heating | Central |
| Cooling | Central Air, Mini-Split Unit(s) |
| Fireplace | No |
Exterior
| Exterior Features | French Doors |
|---|---|
| Roof | Shingle |
| Foundation | Crawlspace |
Additional Information
| Date Listed | October 23rd, 2025 |
|---|---|
| Days on Market | 1 |
| Zoning | RSF3 |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Agent | Justin Shirley |
|---|---|
| Office | SHIRLEY INTERNATIONAL REALTY |