Recently Viewed Properties
See This Home
Save This Listing
Close

$1,125,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 2,100 Sq. Ft.
See This Home
Save This Home
See This Home
Save This Home
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

  • Sold For: $1,125,000
  • Taxes: $9,776 (2025)
  • Status: Closed
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4669581
  • Added to Site: 132 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
  • Living Area: 2,100 Sq. Ft.
  • 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
Sold by Property Lions Realty, Inc

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

Date
Details
Price
Change
Source
2/09/2026
Sold
$1,125,000
-10%
MLS
10/23/2025
Listed
$1,250,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Shirley International Realty
Sold by Property Lions Realty, Inc

Similar Properties near 5244 Winding Way

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

5151 St Albans Ave, Sarasota, FL 34242 - Photo 1
$1,095,000

5151 St Albans Ave  Sarasota, FL 34242

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 2,314
    Sq. Ft.
Listed by Compass Florida Llc
5025 Marsh Field Rd, Sarasota, FL 34235 - Photo 1
$1,129,000

5025 Marsh Field Rd  Sarasota, FL 34235

  • Single Family
  • Active
  • Updated 7 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 2,910
    Sq. Ft.
Listed by Platinum Real Estate
8930 Bloomfield Blvd, Sarasota, FL 34238 - Photo 1 Price Reduced
-$45,000 (-3.77%)
$1,150,000

8930 Bloomfield Blvd  Sarasota, FL 34238

  • Single Family
  • Active
  • Updated 4 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,924
    Sq. Ft.
Listed by Hunt Brothers Realty, Inc.
6961 Scrub Jay Dr, Sarasota, FL 34241 - Photo 1
$1,100,000
Open House

6961 Scrub Jay Dr  Sarasota, FL 34241

  • Single Family
  • Active
  • Updated 8 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 4,177
    Sq. Ft.
Listed by Exp Realty Llc

Just Listed near 5244 Winding Way

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

2055 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Just Listed
$699,000

2055 Gulf of Mexico Dr  #G2-102  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,492
    Sq. Ft.
Listed by Bruce Myer Group (941) 383-6411
5055 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Just Listed
$585,000

5055 Gulf of Mexico Dr  #412  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,484
    Sq. Ft.
Listed by The Ackerman Group (941) 780-6045
350 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Just Listed
$1,675,000

350 Gulf of Mexico Dr  #219  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 5 days ago
  • 2
    Beds
  • 3
    Total Baths
  • 2,378
    Sq. Ft.
Listed by Kepecz-Hays (941) 366-8070
3459 Byron Ln, Longboat Key, FL 34228 - Photo 1 Just Listed
$899,000

3459 Byron Ln  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,474
    Sq. Ft.
Listed by Bruce Myer Group (941) 383-6411

Price Reduced near 5244 Winding Way

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

450 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$26,000 (-3.59%)
$699,000

450 Gulf of Mexico Dr  #B207  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,474
    Sq. Ft.
Listed by Mairead Smialek (847) 334-4848
225 Sands Point Rd, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$51,000 (-6.8%)
$699,000

225 Sands Point Rd  #7205  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 1 day ago
  • 1
    Bed
  • 1
    Total Bath
  • 642
    Sq. Ft.
Listed by Bruce Myer Group (941) 383-6411
1125 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$50,000 (-5.56%)
$849,000

1125 Gulf of Mexico Dr  #101  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,172
    Sq. Ft.
Listed by Pettingell Professionals (941) 383-6411
1211 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$74,000 (-4.23%)
$1,675,000

1211 Gulf of Mexico Dr  #301  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 2 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,100
    Sq. Ft.
Listed by The Ackerman Group (941) 780-6045

Recent Sales near 5244 Winding Way

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

5750 Midnight Pass Rd, Sarasota, FL 34242 - Photo 1 Sold
$962,500

5750 Midnight Pass Rd  #203  Sarasota, FL 34242

  • Condo
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,335
    Sq. Ft.
Listed by Waterside Realty Llc
Sold by Jules Lojacono Mackie
5760 Midnight Pass Rd, Sarasota, FL 34242 - Photo 1 Sold
$1,100,000

5760 Midnight Pass Rd  #307D  Sarasota, FL 34242

  • Condo
  • Closed
  • Updated 8 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,361
    Sq. Ft.
Listed and Sold by Tina Johns
5760 Midnight Pass Rd, Sarasota, FL 34242 - Photo 1 Sold
$1,094,550

5760 Midnight Pass Rd  #404  Sarasota, FL 34242

  • Condo
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,361
    Sq. Ft.
Listed by Berkshire Hathaway Homeservice
Sold by Re/Max Palm
1233 Dockside Pl, Sarasota, FL 34242 - Photo 1 Sold
$975,000

1233 Dockside Pl  #207  Sarasota, FL 34242

  • Condo
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 1,737
    Sq. Ft.
Listed by Michael Saunders & Company
Sold by Premier Sotheby's International Realty

5244 Winding Way, Sarasota, FL 34242 (MLS# A4669581) is a Single Family property that was sold at $1,125,000 on February 09, 2026. 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.