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PRICE $1,250,000 dsIDX morgage calculator
BEDS 4
BATHS 4
HOME SIZE 2,100 sqft
LOT SIZE 9,584 sqft

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

DAYS ON MARKET 58 LAST UPDATED 10/23/2025
TRACT TWIN OAK POND YEAR BUILT 1967
COMMUNITY 34242 - Sarasota/Crescent Beach/Siesta Key GARAGE SPACES 3.0
COUNTY Sarasota STATUS Active
PROPERTY TYPE(S) Single Family


ADDITIONAL DETAILS
AIR Central Air
AIR CONDITIONING Yes
APPLIANCES Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
AREA 34242 - Sarasota/Crescent Beach/Siesta Key
BASEMENT Crawl Space
CONSTRUCTION Wood Siding
GARAGE Yes
HEAT Central
INTERIOR Open Floorplan, Walk-In Closet(s)
LOT 9583 sq ft
POOL Yes
POOL DESCRIPTION Gunite, In Ground, Private
SEWER Public Sewer
STORIES 2
SUBDIVISION TWIN OAK POND
TAXES 9776
UTILITIES Cable Available, Cable Connected
WATER Public
MORTGAGE CALCULATOR
   

TOTAL MONTHLY PAYMENT

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CONTACT US ABOUT 5244 WINDING WAY
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Listing provided by Justin Shirley, SHIRLEY INTERNATIONAL REALTY, 941-448-4872
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 12/19/25 12:42 PM PST.

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