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USAFLSarasotaTwin Oak Pond5244 Winding Way
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5244 Winding Way, SARASOTA, FL

House

For Sale

Listed price in listed location currency (USD).
$1,250,000

440
  • Key Facts
  • Description
  • Rooms
  • Map

Key Facts

Type Single Family Residence
Levels Residential
Size 2100 sqft
Garage Yes
Taxes $9,776
Days Active 0
Lot Size 
Approx. Age 1967
Avg. Price Per Sqft $595
MLS® Number A4669581

Property Address: 5244 Winding Way, SARASOTA, FL, 34242-1848

Average square foot calculated using Size range provided by listing agent.

Description

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
MLS® NumberA4669581
Laundry LevelInside, Other
Central VacNo
FireplaceNo
Acreage0.22
Exterior
GarageYes
Approx. Age1967
Basement
Driveway
Garage Spaces
Heat
A/C
Heating Fuel

Extras

Rooms

Change to metres

Living Room:First FloorNot available
Other:First FloorNot available
Kitchen:First FloorNot available

Similar Listings

Price History

-End Date
Not Sold YetSold Price

For Sale

Oct 24, 2025List Date
$1,250,000List Price

Home Appraisal

This property is estimated to sell between: $1,250,000 and $1,630,000.
Similar properties in this area sold on average for: $1,503,230
Expected to sell in 85 days. Similar properties sold in 85 days. This home has been on eXp Commercial Brokerage for 0 days.

The estimated sale price does not take into account many variables such as recent renovations, type of appliances, school district etc. To get a more accurate estimate please contact agent.

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5244 Winding Way, SARASOTA, FL

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