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5244 Winding Way, 
Sarasota, FL 34242

$1,250,000


4

Beds


4

Baths


2,100

Sq Ft


Single Family

Active

Listed by

Justin Shirley

Shirley International Realty

Last updated:

October 24, 2025, 12:13 PM

MLS#

A4669581

Source:

MFRMLS

About This Home

5244 Winding Way

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

Home Facts

Single Family

4 Baths

4 Bedrooms

Built in 1967

Price Summary

1,250,000

$595 per Sq. Ft.

MLS #:

A4669581

Last Updated:

October 24, 2025, 12:13 PM

Added:

2 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

4

Interior

Living Area:

2,100 Sq. Ft.


Structure

Structure

Building Area:

2,100 Sq. Ft.

Year Built:

1967


Lot

Lot Size (Sq. Ft):

9,664


Finances & Disclosures

Finances

Price:

$1,250,000

Price per Sq. Ft:

$595 per Sq. Ft.

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The information being provided by Stellar Mls is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Stellar Mls. Shirley International Realty is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Shirley International Realty, a broker participant of Stellar Mls. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Stellar Mls and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited. Properties in listings may have been sold or may no longer be available. Copyright 2025 Stellar Mls. All rights reserved.

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