Skip to content
Property for sale at 5244 WINDING WAY, SARASOTA, FL, 34242

5244 Winding WaySarasota, FL, 34242

4beds
4baths
2,100sqft
Single Family Residence
Built in 1967
$1,125,000
Sold
Price per sqft
$536
Sold on
Feb 9, 2026
MLS #A4669581Updated Feb 12, 2026

About this property

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

Interested in this property?
Gaby, Property Specialist
Speak to GabyProperty Specialist, SerhantGaby can share what this home sold for, and find you comparable properties still on the market.
+1 (407) 490-0475
No pressure. Your details stay private.

Property details

Property type
Single Family Residence
Street address
5244 Winding Way
City
Sarasota
State
FL
ZIP code
34242
Year built
1967
New construction
No
Faces
North
Rooms
3
Living area
2,100 sqft
Total building area
2,100 sqft
Levels
Two

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at November 8, 2026 at 2:00 AM EST

Price & sale history

EventPrice
SoldMLS #A4669581$1,125,000
Listed for saleMLS #A4669581$1,250,000
SoldMLS #A4536537$1,300,000
Listed for saleMLS #A4536537$1,245,000
History may be incomplete.
Explore nearby sales

Location

Property for sale at 5244 WINDING WAY, SARASOTA, FL, 34242
Learn more about this propertyGet in touch for more information
We will use your details to respond to this request and may share them with a suitable real estate professional when needed. Marketing is optional.