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$1,250,000 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 2,100 Sq. Ft.
  • Updated 5 days ago
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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

Full Property Details for 5244 Winding Way

General

  • Price: $1,250,000
  • Taxes: $9,776 (2025)
  • Status: Pending
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4669581
  • Updated: 1/12/2026
  • Added to Site: 86 day(s) ago

Rental Information

  • Min. Lease: 1 Month

Interior

  • Number of Rooms: 3
  • Interior Features: Kitchen and Family Room Combination, Open Floorplan, Solid Surface Counters, Walk-In Closet(s)
  • Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • Flooring: Ceramic Tile, Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Inside, Other

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Gunite, In Ground

Exterior

  • Exterior Features: French Doors

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3

Location

  • Area: 34242 - Sarasota/Crescent Beach/Siesta Key
  • County: Sarasota
  • Development Name: 34242 - Sarasota/Crescent Beach/Siesta Key
  • Subdivision: TWIN OAK POND
  • Driving Directions: Higel to Midnight Pass * South on Midnight pass to west on Winding way * Home is located at 5244 winding way
  • Direction Faces: North

Community

  • Community Name: 34242 - Sarasota/Crescent Beach/Siesta Key
  • Association: Yes

Heating & Cooling

  • Cooling Type: Central Air, Mini-Split Unit(s)
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable Connected

Structural Information

  • Exterior Const.: Wood Siding
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 2,100
  • Sq. Ft. Source: Owner
  • Year Built: 1967

Lot Features

  • Lot Size (Acres): 0.22
  • Lot Size (Sq. Ft.): 9,664
  • Lot Size: 9664
  • Street/Road Desc.: Asphalt

Financial Considerations

  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Optional
  • Tax Amount: $9,776
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 9 TWIN OAK POND
  • Flood Zone Info: AE
  • APN: 82010022
  • Property ID: 82010022

Listed by Shirley International Realty

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Listing agent

— 5244 Winding Way —

  • Shirley International Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5244 Winding Way

School District:Sarasota County School District
NameGradesDistance
Phillippi Shores Elementary School
4747 South Tamiami Trail, Sarasota, FL 34231
PK-51.5 mi
Brookside Middle School
3636 South Shade Avenue, Sarasota, FL 34239
6-82.3 mi
Sarasota High School
2155 Bahia Vista Street, Sarasota, FL 34239
9-123.7 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5244 Winding Way Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/23/2025
Listed
$1,250,000
-3.85%
MLS
7/13/2022
Sold
$1,300,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5244 Winding Way

Year
Property Taxes
Change
Tax Assessment
Change
2025
$9,507
-14%
$828,300
-8%
2024
$11,043
-2%
$903,500
-3%
2023
$11,320
38%
$926,700
19%
2022
$8,219
24%
$778,800
45%
2021
$6,609
—
$537,400
17%
2021
$6,609
19%
$459,300
19%
2019
$5,555
2%
$385,497
10%
2018
$5,450
10%
$350,452
-12%
2017
$4,976
2%
$397,200
6%
2016
$4,863
22%
$373,700
42%
2015
$3,991
-1%
$263,300
-1%
2014
$4,031
6%
$265,000
9%
2013
$3,801
—
$243,900
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Shirley International Realty

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5244 Winding Way, Sarasota, FL 34242 (MLS# A4669581) is a Single Family property with 4 bedrooms and 4 full bathrooms. 5244 Winding Way is currently listed for $1,250,000 and was received on October 23, 2025. Want to learn more about 5244 Winding Way? Do you have questions about finding other Single Family real estate for sale in Sarasota? You can browse all Sarasota real estate or contact a Coldwell Banker agent to request more information.

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