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$550,000

  • Sold
  • Closed
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,137 Sq. Ft.
  • Updated 4 days ago
See This Home
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See This Home
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Opportunity knocking loudly! Here it is the least expensive pool home on Siesta Key. You will approach under a charming, canopy lined street. This 2BR/2BA is ready for someone to put their finishing touches on it after hurricane damage. Walls have been removed from 4 ft down, kitchen cabinets and counter removed. Nice Crown molding. Electrical was rewired and raised. Replumbed in 2020. Tankless water heater is 1 year old. A/C was new in 2023. Ductwork was replaced. Great Lap pool has new pool pump. Roof was patched and not leaking. This fabulous quiet location is a half a mile to the #1 Siesta Key Beach, this is your new place in the sun. Island living at its best.

Full Property Details for 5222 Winding Way

General

  • Sold For: $550,000
  • HOA FEE: $35/month
  • HOA FEE FREQ.: Annually
  • Taxes: $3,489 (2024)
  • Status: Closed
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4659769
  • Added to Site: 218 day(s) ago

Rental Information

  • Min. Lease: 1 Month

Interior

  • Number of Rooms: 9
  • Interior Features: Crown Molding, Thermostat
  • Appliances: Microwave
  • Furnishings: Unfurnished
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

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

Exterior

  • Exterior Features: Private Mailbox, Sliding Doors
  • Deck/Patio: Front Porch, Porch, Screened
  • Porch/Patio/Deck: Front Porch, Porch, Screened

Parking

  • Carports: Yes
  • Carport: 1
  • Carport Spaces: 1
  • Covered Spaces: 1

Location

  • Area: 34242 - Sarasota/Crescent Beach/Siesta Key
  • County: Sarasota
  • Development Name: 34242 - Sarasota/Crescent Beach/Siesta Key
  • Subdivision: TWIN OAK POND
  • Driving Directions: Midnight Pass Rd to West on Winding Way (just north of St. Michaels church) go right.
  • Direction Faces: East

School Information

  • Elementary School: Phillippi Shores Elementary
  • Middle School: Brookside Middle
  • High School: Sarasota High

Community

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

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Electricity Connected, Phone Available, Sewer Connected, Water Connected

Structural Information

  • Architectural Info: Patio, Ranch
  • Architectural Style: Patio, Ranch
  • Exterior Const.: Stucco
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,137
  • Sq. Ft. Source: Public Records
  • Living Area: 1,137 Sq. Ft.
  • Year Built: 1963

Lot Features

  • Lot Size (Acres): 0.14
  • Lot Size (Sq. Ft.): 6,000
  • Lot Size: 6000
  • Lot Dimensions: 60 x 100
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt
  • Fencing (Description): Vinyl

Water Features

  • Water Front Desc.: Lake

Financial Considerations

  • Association Fee: $414
  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Optional
  • Tax Amount: $3,489.52
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 20 TWIN OAK POND
  • Flood Zone Info: AE
  • APN: 82010033
  • Property ID: 82010033

Listed and Sold by Michael Saunders & Company

Listing agents

— 5222 Winding Way —

  • Michael Saunders & Company

  • Michael Saunders & Company

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 5222 Winding Way

School District:Sarasota County School District
NameGradesDistance
Phillippi Shores Elementary School
4747 South Tamiami Trail, Sarasota, FL 34231
PK-51.6 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 5222 Winding Way

Date
Details
Price
Change
Source
11/12/2025
Sold
$550,000
-3.49%
MLS
7/28/2025
Listed
$569,900
—
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 and Sold by Michael Saunders & Company

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5222 Winding Way, Sarasota, FL 34242 (MLS# A4659769) is a Single Family property that was sold at $550,000 on November 12, 2025. Want to learn more about 5222 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.