$1,250,000

5244 WINDING WAY, Sarasota, FL 34242

4 beds |
4 baths |
2,100 sqft

Single-Family Home
Built in 1967
9,583sqft lot
3 car garage
$595/sqft
Listed 4 days ago

Property Description

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

Listing Status:: Active
Date Added:: October 23, 2025 at 05:00AM
Listing Office:: SHIRLEY INTERNATIONAL REALTY : 941-448-4872
Listing Agent:: Justin Shirley : 941-448-4872
MLS ID:: A4669581

General: Kitchen/Family Room ComboOpen FloorplanSolid Surface CountersWalk-In Closet(s)
Appliances: DishwasherDryerMicrowaveRangeRefrigeratorWasher
Laundry: InsideOther
Flooring: Ceramic TileVinyl
A/C: Central AirMini-Split Unit(s)
Heating: Central

General: French Doors
Pool: GuniteIn Ground

Roofing: Shingle
General: Wood SidingTwoCrawlspace

Road/Access: Asphalt
HOA Amenities: Annually
Originating MLS: mfrmls
County: Sarasota

Zoning: RSF3LOT 9 TWIN OAK POND0082010022

Utilities: BB/HS Internet AvailableCable Connected
Water: Public
Sewer: Public Sewer

Source: mfrmls
Ownership: Fee Simple

This listing courtesy of Justin Shirley, SHIRLEY INTERNATIONAL REALTY

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

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Location

Schools Nearby

Ese Special Programs

1960 Landings Blvd, Sarasota, FL, 34231

Grades PK-12

1.06 miles away

Ese Special Programs

1960 Landings Blvd, Sarasota, FL, 34231

Grades PK-12

1.06 miles away

Sarasota Virtual Instruction (Course Offerings)

1960 Landings Blvd, Sarasota, FL, 34231

Grades 9-12

1.06 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.