5239 WINDING, SARASOTA, FL 34242

$799,000 Was $870,000

Beds: 3

Baths: 2 Full

Sq. Ft.: 1,512 Sq. Ft.

Year Built: 1958

Lot Size: 0.21 Acres

Garage: N/A

Pool: Yes

DOM: 69

Property Overview

Status: Closed

Property Type: Residential

MLS #: 2af655cc177b556ff155c2118617ece1

Subdivision: TWIN OAK POND

County: Sarasota

HOA Fee: $414 (Annually)

Year Built: 1958

Construction: Wood Frame, Wood Frame (FSC Certified), Wood Siding

Foundation: Other, Slab

Roof: Shingle

Cooling: Central Air

Heating: Electric

Sewer: Public Sewer

Water Source: Public

Zoning: RSF3

Tax Amount: $10,388.47 (2024)

Date Sold: Apr 30, 2025

Sold Price: $630,000

Listed On: Feb 7, 2025

Description

***PRICE IMPROVMENT*** ***PRICE IMPROVEMET*** Discover your own private oasis at 5239 Winding Way, just minutes from Siesta Beach. Come and see for yourself this lovely and charming home that is an absolute MUST SEE! Nestled in a canopy-protected neighborhood, this property features a spacious open floor plan that connects the kitchen and living areas, creating a perfect space for entertaining friends and family. The kitchen is fully equipped with a large pantry, ceiling-to-counter tiled backsplash, and a peninsula island. The living room is filled with natural lighting from the numerous windows, and features custom built-in shelves, a tongue and groove ceiling, ship lap paneling that makes the space feel inviting and cozy. The primary bedroom is filled with natural light and boasts two large windows. The primary bathroom is equally impressive with marble tile shower surround, penny tile shower floor and frameless glass shower frame. The secondary bedrooms are spacious and quaint. The large backyard and heated pool make outdoor events a breeze, and the perimeter privacy fence, lush trees, and rear water provide ultimate privacy. Siesta Key, is an 8-mile-long island located just a short bridge crossing west of Sarasota, offers stunning quartz-sand beaches and a plethora of outdoor recreational activities – from fishing to parasailing.

Exterior Features

Awning(s), French Doors, Other

Directions

Siesta Dr. to Higel Ave. Left on Mangrove Point Rd to Midnight Pass Rd. Right on Winding Way to home.

School Information

Elementary: Phillippi Shores Elementary

Middle: Brookside Middle

High: Sarasota High

Location

Get Directions View on Google Maps

Mortgage Estimator

*Estimate includes Principal & Interest (P&I) only. It does not include taxes, insurance, HOA fees, or PMI. Rates and payments may vary. Consult a lender for accurate figures.

Listing Information

Provided Courtesy of:

BALDWIN PARK REALTY LLC

Listing Agent: Brian Cirillo

Information is deemed reliable but not guaranteed. Information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data last updated: July 31, 2025, 11:32 pm UTC

MLS Source: Stellar MLS Copyright © 2025

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