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$1,250,000
1 Day On Site

5244 WINDING WAY
SARASOTA, FL 34242

For Sale|Single Family Residence|Active
4
Beds
4
Total Baths
4
Full Baths
2,100
SqFt
$595
/SqFt
1967
Built
Subdivision:
TWIN OAK POND
County:
Sarasota
5244 WINDING WAY5244 WINDING WAY5244 WINDING WAY5244 WINDING WAY
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Monthly Payment (Est.)

$5,703
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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

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Listing Snapshot
Price 
$1,250,000
Days On Site 
1 Day
Bedrooms 
4
Inside Area (SqFt) 
2,100 sqft
Total Baths 
4
Full Baths 
4
Partial Baths 
N/A
Lot Size 
0.22 Acres
Year Built 
1967
MLS® Number 
A4669581
Status 
Active
Property Tax 
$9,776
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Owner
Friends & Family
Recent Activity
57 minutes agoListing updated with changes from the MLS®
9 hours agoStatus changed to Active
yesterdayListing first seen on site
General Features
Acres 
0.22
Direction Faces 
North
Garage 
Yes
Garage Spaces 
3
Levels 
Two
Pets 
Yes
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
SqFt Total 
2100
Utilities 
Cable AvailableCable Connected
Water Source 
Public
Zoning 
RSF3
Interior Features
Appliances 
DishwasherDryerMicrowaveRangeRefrigeratorWasher
Basement 
Crawl Space
Cooling 
Central Air
Flooring 
Ceramic TileVinyl
Heating 
Central
Interior 
Open FloorplanWalk-In Closet(s)
Laundry Features 
InsideOther
Kitchen 
Level - First
Living Room 
Level - First
Master Bedroom 
Level - First
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Exterior Features
Construction Details 
Wood Siding
Pool Features 
GuniteIn GroundPrivate
Private Pool 
Yes
Roof 
Shingle
Community Features
Financing Terms Available 
CashConventional
HOA Fee Frequency 
Annually
MLS Area 
34242 - Sarasota/Crescent Beach/Siesta Key
Roads 
Asphalt
Township 
37
Listing courtesy of SHIRLEY INTERNATIONAL REALTY 9414484872



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2025, Stellar MLS.
Last checked: 2025-10-24 06:22 AM EDT

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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