by Global Lifestyle Properties

See Home Value
$1,125,000
● House - Off Market

5244 WINDING WAY

SARASOTA, FL 34242
bedrooms
4 Beds
bathrooms
4 Baths
square feet
2,100 Ft²
$6,953
Est. Monthly

About This Property

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
Unit Size
2,100 Ft²
Days on Market
109 days
Land Size
0.22 acres
Price per sqft
$595
Property Type
House
Property Taxes
$815
HOA Dues
-
Year Built
1967

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Last updated: 9 months ago (Stellar MLS #A4669581)

Price History

Date / Event Date Event Price
Feb 9, 2026 Sold
Sold
Jan 13, 2026 In contract -
In contract
Oct 23, 2025 Listed by SHIRLEY INTERNATIONAL REALTY $1,250,000
Listed by SHIRLEY INTERNATIONAL REALTY
Jul 14, 2022 Sold
Sold
May 24, 2022 Listed by SHIRLEY INTERNATIONAL REALTY $1,245,000
Listed by SHIRLEY INTERNATIONAL REALTY

Property Highlights

Garage
Air Conditioning

Building Info

Overview

    General

  • Year Built: 1967
  • Effective Year Built: 2002
  • Building Count: 1
  • Total Rooms: 6
  • Bedroom Count: 3
  • Bathroom Count: 3
  • Full Bathrooms: 3
  • Partial Bathrooms: 3
  • Building Condition: 6
  • Building Quality: 7
  • Construction Type: 17
  • Building Style: 0
  • Exterior Walls Type: 18
  • Interior Walls Type: 3
  • Roof Shape Type: 1
  • Roof Cover Type: 15
  • Floor Count: 200
  • Living Units: 1
  • Floor Cover: 15
  • Basement Type: 0
  • Basement Area: 0
  • Garage Type: 4
  • Garage Square Area: 876
  • Parking Space Count: 4
  • Patio Type: 69
  • Porch Type: 102
  • Pool Type: 8
  • Location Influence Type: 113

    Dimensions

  • Lot Size Square Feet: 9,664
  • Lot Size Depth Feet: 1,410
  • Lot Size Frontage Feet: 720
  • Total Building Area: 1,802
  • Gross Building Area: 1,802
  • Building Area: 1,802
  • Building Area Measurement: L

    Heating and Cooling

  • Air Conditioning: 1
  • Heating: 3
  • Heated Square Feet: 1,802
  • Heating Fuel Type: 0

    Utilities

  • Sewer System: 1
  • Water Service: 2

Building

  • Building Type: 0
  • Property Class: R
  • Subdivision: TWIN OAK POND
  • Land Acres: 0000000222
  • Standard Land Use Code: 1001
  • County Land Use Code: 0100
  • State Land Use Code: 001
  • Legal Description 1: LOT 9 TWIN OAK POND

Neighborhood

  • School District Name: Sarasota County School District
  • School Tax School District: L018 A055 F052
  • Census Tract: 001904

Zoning

  • Zoning: RSF3

Geography

  • Assessors Map Reference: 28A
  • Account Number: 0082010022
  • Subdivision Tract Number: 1183
  • Parcel: 0082-01-0022
  • Lot: 9
  • Meridian: SEC 12 TWN 37S RNG 17E
  • Municipality: SARASOTA COUNTY
  • Latitude: 27.2751
  • Longitude: -82.5483

    Address

  • Full Address: 5244 Winding Way
  • Address - House Number: 5244
  • Address - Street Name: Winding
  • Address - Suffix Type: Way
  • State: FL
  • City Name: Sarasota
  • Carrier Code: C061
  • 4-Digit Zip Code: 1848
  • Zip Code: 34242

Valuation

    Tax

  • Total Area: 1,834
  • Tax Year: 2023
  • Tax Amount: $1,132,002
  • Tax Rate Code Area: 1800

    Appraisal Valuation

  • Standard Deviation: 0.082
  • Valuation Date: Jan 10, 2024
  • Confidence Score: 93
  • Final Value: 1,616,566
  • High Value: 1,749,169
  • Low Value: 1,483,964

    Market Valuation

  • Market Total Value: $926,700
  • Market Land Value: $584,900
  • Market Improvement Value: $341,800

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $926,700
  • Assessed Land Value: $584,900
  • Assessed Improvements Value: $341,800

    Sales

  • Current Sale Contract Date: Jul 13, 2022
  • Current Sale Recording Date: Jul 14, 2022
  • Current Sale Price:
  • Current Sale Document Type: 71
  • Current Sale Input Document Number: 117825
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Twin Oak Pond


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Frequently Asked Questions

When was property at 5244 Winding Way built and last sold?
The property at 5244 Winding Way was built in 1967 and last sold on Jul 13, 2022 for $1,300,000.
How much is this home worth?
The estimated value of the home located at 5244 Winding Way is $1,267,330.
What are some comparable homes to 5244 Winding Way?
There are currently no comparable homes to 5244 Winding Way.