SARASOTA, FL 34242 5244 WINDING WAY

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Presented By: SHIRLEY INTERNATIONAL REALTY with 941-448-4872. - 941-448-4872
  • MLS# A4669581
  • 10/23/2025
  • Request Tour
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Disclaimer: The information contained in this listing has not been verified by Homepride Group at EXP Realty and should be verified by the buyer.
  • Beds • 4
  • Baths • 4
  • SQFT • 2,100
  • Garage • 3

Home Details

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
Presented By: SHIRLEY INTERNATIONAL REALTY with 941-448-4872. - 941-448-4872

Interior Features for 5244 WINDING WAY

Bedrooms

Total Bedrooms4

Bathrooms

Half Baths0
Total Baths4

Other Interior Features

LivingAreaSourceOwner
Air Conditioning Y/NYes
Fireplace Y/NNo
FlooringCeramic Tile, Vinyl
Heating Y/NYes
Interior AmenitiesKitchen/Family Room Combo, Open Floorplan, Solid Surface Counters, Walk-In Closet(s)
Laundry FeaturesInside, Other

General for 5244 WINDING WAY

Additional Parcels Y/NNo
AppliancesDishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Assoc Fee Paid PerAnnually
Attached Garage No
Building Area UnitsSquare Feet
Carport Y/NNo
CitySARASOTA
Construction MaterialsWood Siding
CoolingCentral Air, Mini-Split Unit(s)
CountySarasota
DirectionsHigel to Midnight Pass * South on Midnight pass to west on Winding way * Home is located at 5244 winding way
Facing DirectionNorth
Flood Zone CodeAE
Full Baths4
Garage Spaces3
Garage Y/NYes
HeatingCentral
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionLOT 9 TWIN OAK POND
LevelsTwo
Listing TermsCash, Conventional
Living Area UnitsSquare Feet
Lot Size Square Feet9664
Lot Size UnitsSquare Feet
MLS Area34242 - Sarasota/Crescent Beach/Siesta Key
Minimum Lease1 Month
New ConstructionNo
Occupancy TypeVacant
OwnershipFee Simple
Pets AllowedYes
Pool FeaturesGunite, In Ground
Property SubtypeSingle Family Residence
Property TypeResidential
RoofShingle
STELLAR_InLawSuiteDescrip1 Bathroom, 1 Bedroom, Kitchenette
STELLAR_InLawSuiteYNNo
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusActive
Subdivision NameTWIN OAK POND
Tax Annual Amount9776
Tax Lot9
Tax Year2025
Total Rooms3
UtilitiesBB/HS Internet Available, Cable Connected
Virtual TourClick here
Water Access Y/NNo
Water View Y/NNo
Year Built1967
ZoningRSF3

Exterior for 5244 WINDING WAY

Building Area Total2100
Covered Spaces3
Exterior AmenitiesFrench Doors
Foundation DetailsCrawlspace
Lot Size Acres0.22
Lot Size Area9664
Private PoolYes
Road Surface TypeAsphalt
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Schools

High School Hubert H Humphrey Middle School
Middle School N/A
Elementary School Big Hollow Elementary School

Steven Pugh

Broker Associate | Team Leader
Price $1,250,000
MLS#A4669581
List Date 10/23/2025
Property Type Single Family
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Request Info
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