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$3,500

  • Sold
  • Closed
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,102 Sq. Ft.
See This Home
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See This Home
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Adorable home for rent on Siesta Key. Less than one mile walk to the beach! Open floorplan with tasteful modern furnishings and huge back porch with no rear neighbors all on a quiet little circle neighborhood with a pond in the middle of the circle. Rent starting at $3000 per month. Rate depends on what time of year the rental is for.

Full Property Details for 5242 Winding Way

General

  • Rent: $3,500
  • Status: Closed
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4601028
  • Added to Site: 685 day(s) ago

Rental Information

  • Min. Lease: 1 Month

Interior

  • Number of Rooms: 5
  • Interior Features: Kitchen and Family Room Combination, Window Treatments
  • Appliances: Dishwasher, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Refrigerator, Washer
  • Furnishings: Furnished
  • Flooring: Terrazzo

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Laundry: Laundry Closet

Exterior

  • Deck/Patio: Covered, Enclosed, Screened
  • Porch/Patio/Deck: Covered, Enclosed, 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: From Midnight pass headed west turn north on Winding Way. Turn left and follow around to address on the left. Sign in the yard

School Information

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

Community

  • Community Name: 34242 - Sarasota/Crescent Beach/Siesta Key
  • Number of Pets: 1
  • Pet Restrictions: Possible breed restrictions due to owner's insurance.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Heat Pump

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Stories/Levels: One
  • Square Feet: 1,102
  • Sq. Ft. Source: Estimated
  • Living Area: 1,102 Sq. Ft.
  • Year Built: 1963

Lot Features

  • Property View: Park/Greenbelt
  • Lot Size (Acres): 0.17
  • Lot Size (Sq. Ft.): 7,547
  • Lot Size: 7547
  • Street/Road Desc.: Asphalt

Financial Considerations

  • Lease Price: $3,000
  • Assoc Fee Desc.: None
  • Application Fee: $50
  • Security Deposit: $350

Disclosures and Reports

  • APN: 82010023
  • Property ID: 82010023

Listed by Keller Williams On The Water S
Sold by Keller Williams On The Water S

Listing agents

— 5242 Winding Way —

  • Keller Williams On The Water S

  • Keller Williams On The Water S

Schools serving 5242 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 History for 5242 Winding Way

Date
Details
Price
Change
Source
8/30/2025
Sold
$3,500
16.67%
MLS
3/03/2024
Listed
$3,000
—
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 Keller Williams On The Water S
Sold by Keller Williams On The Water S

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Listed and Sold by Fine Properties

5242 Winding Way, Sarasota, FL 34242 (MLS# A4601028) is a Single Family property that was sold at $3,500 on August 30, 2025. Want to learn more about 5242 Winding Way? Do you have questions about finding other real estate for sale or rent in Sarasota? You can browse all Sarasota rentals or contact a Coldwell Banker agent to request more information.