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5244 Winding Way, Sarasota, FL

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$1,250,000

($595/sqft)

List Status: Active
5244 Winding Way
Sarasota, FL 34242


4 beds
4 baths
2100 living sqft
Top Features
  • Subdivision: Twin Oak Pond
  • Built in  1967
  • Single Family Residence
Description
Property Details
Additional Information
Additional Lease Restrictions
Inquire with Sarasota county
Additional Parcels YN
false
Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Approval Process
Inquire w Sarasota county
Association Fee Frequency
Annually
Association Fee Requirement
Optional
Association YN
true
Attached Garage YN
false
Available For Lease YN
1
Bathrooms Total Integer
4
Building Area Source
Owner
Building Area Total
2100
Building Area Total Srch SqM
195.10
Building Area Units
Square Feet
Calculated List Price By Calculated SqFt
595.24
Carport YN
false
Construction Materials
Wood Siding
Cooling
Central Air, Mini-Split Unit(s)
Country
US
Cumulative Days On Market
1
Current Price
1250000.00
Direction Faces
North
Exterior Features
French Doors
Fireplace YN
false
Flood Zone Code
AE
Flood Zone Date
2016-11-04
Flood Zone Panel
12115C0143F
Flooring
Ceramic Tile, Vinyl
Foundation Details
Crawlspace
Garage Dimensions
17x30
Garage Spaces
3
Garage YN
true
Heating
Central
Interior Features
Kitchen/Family Room Combo, Open Floorplan, Solid Surface Counters, Walk-In Closet(s)
Internet Address Display YN
true
Internet Automated Valuation Display YN
true
Internet Consumer Comment YN
false
Internet Entire Listing Display YN
true
Laundry Features
Inside, Other
Lease Restrictions YN
1
Levels
Two
List AOR
Sarasota - Manatee
Living Area Meters
195.10
Living Area Source
Owner
Living Area Units
Square Feet
Lot Size Acres
0.22
Lot Size Square Feet
9664
Lot Size Square Meters
898
Minimum Lease
1 Month
Modification Timestamp
2025-10-24T10:53:42.858Z
New Construction YN
false
Num Times per Year
12
Occupant Type
Vacant
Ownership
Fee Simple
Parcel Number
0082010022
Pets Allowed
Yes
Pool Private YN
true
Postal Code Plus 4
1848
Public Remarks
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
Public Survey Range
17
Public Survey Section
12
RATIO Current Price By Calculated SqFt
595.24
Road Surface Type
Asphalt
Roof
Shingle
Room Count
3
SW Subdiv Community Name
Twin Oak Pond
Senior Community YN
false
Sewer
Public Sewer
Showing Requirements
ShowingTime
Status Change Timestamp
2025-10-24T01:56:43.000Z
Tax Annual Amount
9776
Tax Book Number
8-35
Tax Legal Description
LOT 9 TWIN OAK POND
Tax Lot
9
Tax Year
2025
Total Acreage
0 to less than 1/4
Total Annual Fees
0.00
Total Monthly Fees
0.00
Township
37
Universal Property Id
US-12115-N-0082010022-R-N
Unparsed Address
5244 WINDING WAY
Utilities
BB/HS Internet Available, Cable Connected
Water Source
Public
Waterfront YN
false
Zoning
RSF3
Neighborhood Map
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MLS #MFRA4669581 Listing courtesy of Shirley International Realty provided by Stellar MLS.

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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; availability of any listing should always be independent verified. Listing information is provided for consumer 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. The source of the listing data is as follows: Stellar MLS (updated 12/8/25 5:52 AM) |

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