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$1,093,937

Listing Price

3beds

3baths

1,802sqft

9,664sqft lot

5244 Winding Way, Sarasota, FL 34242

Member Features

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  • Full foreclosure details

  • Home value, equity and ownership info

  • Find homes priced below market

  • Get full access with a FREE Account

Already a member?

For Sale

Off Market

Single Family

Home type

607.07

Price / sqft

1967

Year built

Home Details

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

Interior Details

Square Feet
  • 1802

Bedrooms
  • 3

Bathrooms
  • 3

Heating
  • Has Heating:

    Yes

  • Heating Type:

    Central

Cooling
  • Has Cooling:

    Yes

  • Cooling Type:

    Central

Fuel
  • Has Fuel:

    No

  • Fuel Type:

    N/A

Basement
  • Has Basement:

    No

  • Basement Type:

    N/A

Flooring
  • Has Flooring:

    No

  • Flooring Type:

    Wood (unspecified)

Fireplace
  • Has Fireplace:

    Yes

  • Fireplace Type:

    N/A

Property Details

Lot Size
  • 9664

Water
  • Yes

Sewer
  • Yes

Parking
  • Type:

    Garage, Detached

  • Location:

    N/A

  • Status:

    N/A

  • Number of Spaces:

    4

Deck
  • No

Patio
  • No

Fence
  • No

Pool
  • No

Porch
  • Yes

Stoop
  • No

Breezeway
  • No

Construction Details

Number of Stories
  • 2

Style
  • N/A

Exterior
  • Wood Siding

Foundation
  • N/A

Roof
  • Gable

Roofing Material
  • Asphalt

Tax History

Year

Amount

Land

Improvement

Percent Change

Assessment

2020

$5,964

$0

$0

--%

$424,047

2019

$5,555

$0

$0

--%

$385,497

2018

$5,449

$0

$0

--%

$350,452

2017

$4,976

$252,200

$145,000

--%

$397,200

2016

$4,863

$220,600

$153,100

--%

$373,700

2014

$4,031

$0

$0

--%

$265,000

2013

$3,801

$0

$0

--%

$243,900

2012

$3,170

$0

$0

--%

$234,873

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Average Home Price in 34242

Nearby Properties

Zip Code

Price

Bed

Bath

Sqft

Lot

Sold Date

$1,342,281

4 Beds

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16,200 Lot (sqft)

Sold 08/22/2026

$2,200,000

3 Beds

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1,921 Sqft

14,500 Lot (sqft)

Sold 08/12/2026

$1,319,053

2 Beds

2 Baths

1,571 Sqft

14,077 Lot (sqft)

Sold 04/17/2026

$1,749,000

2 Beds

2 Baths

1,772 Sqft

12,100 Lot (sqft)

Sold 10/06/2026

$1,093,937

3 Beds

3 Baths

1,802 Sqft

9,664 Lot (sqft)

Sold 10/06/2026

$999,999

3 Beds

2 Baths

1,644 Sqft

13,500 Lot (sqft)

Sold 10/06/2026

$1,668,888

3 Beds

3 Baths

1,798 Sqft

14,900 Lot (sqft)

Sold 10/06/2026

$1,295,000

3 Beds

3 Baths

1,896 Sqft

5,851 Lot (sqft)

Sold 07/10/2025

$1,025,000

4 Beds

3 Baths

1,967 Sqft

6,235 Lot (sqft)

Sold 09/29/2026

percent-home-icon

Calculators

Mortgage

Mortgage Calculator

Calculate your monthly mortgage payments.
Household Income
70,000
$
Home price
1,093,937
$
Down payment
218,787.40
$
Mortgage Rate
6.5
%
Loan Term
Property Tax Rate
1.1
%
Homeowner's Insurance (Annual)
6,563.62
$
HOA (Monthly)
0
$
PMI
0
$
$7,081
Your Payment
Total Monthly Payment:$7,081
Percent of Income:121%
Affordable:No

Details for 5244 WINDING WAY

Property Debt

Foreclosure Contact Details