Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$230,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 1 Full Bath
  • 1,120 Sq. Ft.
  • 2 Car Garage
  • Updated 7 hours ago
See This Home
Save This Home
See This Home
Save This Home
Welcome home to this charming three-bedroom ranch offering comfortable single-level living and endless potential. Featuring a full basement, a detached two-car garage, and a fully fenced backyard, this property provides plenty of space for storage, recreation, gardening, or entertaining. The front yard is beautifully accented with mature landscaping and colorful flowers, creating inviting curb appeal. Inside, you'll find a solid home that is ready for your personal touch. Bring your decorating ideas and a fresh coat of paint to unlock the property's full potential. With only minimal cosmetic updates needed, this is an excellent opportunity for homeowners, investors, or anyone looking to build equity. Conveniently laid out and full of possibilities, this home offers a great foundation to create the space you've always envisioned. Currently tenant-occupied. Property is being sold As-Is.

Full Property Details for 5303 S Winchester Ave

General

  • Price: $230,000
  • Taxes: $2,421 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MRED
  • MLS ID: 12650207

Interior

  • Basement: Unfinished

Rooms

Bathrooms

  • Total Bathrooms: 1
  • Full Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Features: Yes, Garage Owned, Detached, Garage

Location

  • Area: CHI - New City
  • County: Cook
  • Township: Jefferson
  • Driving Directions: TAKE DAMEN N OR S TO 53RD ST E TO ADDRESS.

School Information

  • School District: 299
  • Elem School District: 299
  • Midd School District: 299
  • High School District: 299

Community

  • Assoc. Fees Include: None

Heating & Cooling

  • Cooling Type: Central Air Conditioning, None
  • Heating Type: Natural Gas

Utilities

  • Sewer: Public Sewer
  • Water: Lake Michigan, Public

Structural Information

  • Construction: Brick
  • Exterior Const.: Brick
  • Basement: Yes
  • Basement Desc.: Unfinished, Full
  • Square Feet: 1,120
  • Sq. Ft. Source: Assessor
  • Year Built: 1959
  • Built Before 1978: Yes
  • Remodeled/Updated: 2015

Lot Features

  • Lot Size Range: Less than .25 Acre
  • Lot Dimensions: 25 x 125

Financial Considerations

  • Parking Included: Yes
  • Assessment Year: 1959
  • Tax Amount: $2,421.82
  • Tax Year: 2024
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Fee Simple
  • Property ID: 20074170020000

Listed by The Leading Realtors Corp.

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 5303 S Winchester Ave —

  • The Leading Realtors Corp.

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Get a Great Insurance Rate

Find the right home insurance for your new home!

with our affiliated in-house agency

Request a Quote

Save up to an additional 20% by bundling your home and auto together!

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Find the right home insurance for your new home!

with our affiliated in-house agency

Request a Quote

Save up to an additional 20% by bundling your home and auto together!

Schools serving 5303 S Winchester Ave

School District:Chicago Public School District 299
NameGradesDistance
Fulton Elementary School, Chicago, IL
5300 South Hermitage Avenue, Chicago, IL 60609
PK-80.2 mi
Tilden Career Communty Academy High School
4747 South Union Avenue, Chicago, IL 60609
9-121.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5303 S Winchester Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/29/2026
Listed
$230,000
1337.5%
MLS
3/29/2012
Sold
$16,000
—
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 5303 S Winchester Ave

Year
Property Taxes
Change
Tax Assessment
Change
2023
$1,075
—
$12,001
137%
2023
$1,075
3%
$5,066
—
2022
$1,048
3%
$5,066
—
2021
$1,019
-31%
$5,066
-23%
2020
$1,472
-1%
$6,563
-11%
2019
$1,491
2%
$7,375
—
2018
$1,466
-21%
$7,375
-13%
2017
$1,847
1%
$8,522
-6%
2016
$1,827
-2%
$9,060
-10%
2015
$1,856
5%
$10,057
7%
2014
$1,761
2%
$9,417
—
2013
$1,726
1%
$9,417
—
2012
$1,704
—
$9,417
—
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.

Estimate the Cost for 5303 S Winchester Ave

$
Down Payment
%
$
%

$
$

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

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by The Leading Realtors Corp.

Similar Properties near 5303 S Winchester Ave

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

4536 W 83rd St, Chicago, IL 60652 - Photo 1
$230,000

4536 W 83rd St  Chicago, IL 60652

  • Single Family
  • Active
  • 3
    Beds
  • 1
    Total Bath
8926 S Lowe Ave, Chicago, IL 60620 - Photo 1
$224,900

8926 S Lowe Ave  Chicago, IL 60620

  • Single Family
  • Active
  • 3
    Beds
  • 1
    Total Bath
  • 1,040
    Sq. Ft.
6641 S University Ave, Chicago, IL 60637 - Photo 1
$221,500

6641 S University Ave  Chicago, IL 60637

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 1
    Total Bath
  • 1,452
    Sq. Ft.
3709 W 66th Pl, Chicago, IL 60629 - Photo 1
$240,000

3709 W 66th Pl  Chicago, IL 60629

  • Single Family
  • Active
  • 3
    Beds
  • 1
    Total Bath
  • 1,038
    Sq. Ft.

Just Listed near 5303 S Winchester Ave

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

3717 S 58th Ct, Cicero, IL 60804 - Photo 1 Just Listed
$229,000

3717 S 58th Ct  Cicero, IL 60804

  • Condo / Townhouse
  • Active
  • Updated 2 hours ago
  • 2
    Beds
  • 1
    Total Bath
  • 946
    Sq. Ft.
333 S East Ave, Oak Park, IL 60302 - Photo 1 Just Listed
$259,900

333 S East Ave  #306  Oak Park, IL 60302

  • Condo
  • Active
  • Updated 7 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,200
    Sq. Ft.
151 N Kenilworth Ave, Oak Park, IL 60301 - Photo 1 Just Listed
$337,500

151 N Kenilworth Ave  #4G  Oak Park, IL 60301

  • Condo
  • Active
  • Updated 19 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,100
    Sq. Ft.
415 S Lombard Ave, Oak Park, IL 60302 - Photo 1 Just Listed
$299,900

415 S Lombard Ave  #304  Oak Park, IL 60302

  • Condo
  • Active
  • Updated 1 hour ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,000
    Sq. Ft.

Price Reduced near 5303 S Winchester Ave

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

5340 W 30th St, Cicero, IL 60804 - Photo 1 Price Reduced
-$5,000 (-1.43%)
$344,900

5340 W 30th St  Cicero, IL 60804

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,143
    Sq. Ft.
5017 W 29th St, Cicero, IL 60804 - Photo 1 Price Reduced
-$10,000 (-3.45%)
$279,900

5017 W 29th St  Cicero, IL 60804

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 1
    Total Bath
  • 1,300
    Sq. Ft.
420 S Kenilworth Ave, Oak Park, IL 60302 - Photo 1 Price Reduced
-$5,900 (-2.62%)
$219,000

420 S Kenilworth Ave  #18  Oak Park, IL 60302

  • Condo
  • Active
  • Updated 1 day ago
  • 2
    Beds
  • 1
    Total Bath
  • 700
    Sq. Ft.
330 N Ridgeland Ave, Oak Park, IL 60302 - Photo 1 Price Reduced
-$11,000 (-2.16%)
$499,000
Open House

330 N Ridgeland Ave  Oak Park, IL 60302

  • Single Family
  • Active
  • Updated 7 hours ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,628
    Sq. Ft.

Recent Sales near 5303 S Winchester Ave

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

2031 W James St, Chicago, IL 60609 - Photo 1 Sold
$255,000

2031 W James St  Chicago, IL 60609

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,450
    Sq. Ft.
5519 S Seeley Ave, Chicago, IL 60636 - Photo 1 Sold
$245,000

5519 S Seeley Ave  Chicago, IL 60636

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,000
    Sq. Ft.
5543 S Honore St, Chicago, IL 60636 - Photo 1 Sold
$205,000

5543 S Honore St  Chicago, IL 60636

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,634
    Sq. Ft.
[Address not provided], Chicago, IL 60609 - Photo 1 Sold
$220,000

[Address not provided]  Chicago, IL 60609

  • Multi-Family
  • Closed
  • 5
    Total Beds

5303 S Winchester Avenue, Chicago, IL 60609 (MLS# 12650207) is a Single Family property with 3 bedrooms and 1 full bathroom. 5303 S Winchester Avenue is currently listed for $230,000 and was received on May 29, 2026. Want to learn more about 5303 S Winchester Avenue? Do you have questions about finding other Single Family real estate for sale in New City? You can browse all New City real estate or contact a Coldwell Banker agent to request more information.

Tour this property