5244 WINDING WAY
SARASOTA, FL, 34242
$1,250,000
4 Beds
4 Baths
2,100 SqFt
0.22 Acres
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$1,250,000
5244 WINDING WAY
SARASOTA, FL, 34242
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

Property Details

Price:
$1,250,000
MLS #:
A4669581
Status:
Active
Beds:
4
Baths:
4
Address:
5244 WINDING WAY
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
TWIN OAK POND
Neighborhood:
34242sarasotacrescentbeachsiestakey
City:
SARASOTA
Listed Date:
Oct 23, 2025
State:
FL
Finished Sq Ft:
2,100
Total Sq Ft:
2,100
ZIP:
34242
Lot Size:
9,664 sqft / 0.22 acres (approx)
Year Built:
1967

Schools

Interior

Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Bathrooms
4 Full Bathrooms
Cooling
Central Air, Mini- Split Unit(s)
Flooring
Ceramic Tile, Vinyl
Heating
Central
Laundry Features
Inside, Other

Exterior

Construction Materials
Wood Siding
Exterior Features
French Doors
Roof
Shingle

Financial

HOA Frequency
Annually
Tax Year
2025
Taxes
$9,776
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5244 WINDING WAY
SARASOTA, FL