5958 S Winchester Avenue Chicago, IL ^$ 140,000

5958 S Winchester Avenue

^$ 140,000

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5958 S Winchester Avenue

Chicago, IL, 60636

^$ 140,000

Bedrooms5 Baths2.0 Sq 1,607

Monthly Estimate*

^$ 862

5958 S Winchester Avenue, Chicago, IL 60636 - Image 1

5958 S Winchester Avenue, Chicago, IL 60636 - Image 2

5958 S Winchester Avenue, Chicago, IL 60636 - Image 3

5958 S Winchester Avenue, Chicago, IL 60636 - Image 4

5958 S Winchester Avenue, Chicago, IL 60636 - Image 5

5958 S Winchester Avenue, Chicago, IL 60636 - Image 6

5958 S Winchester Avenue, Chicago, IL 60636 - Image 7

5958 S Winchester Avenue, Chicago, IL 60636 - Image 8

Single Family Home for sale in Chicago, IL

for $140,000 with 5 bedrooms and 2 full baths. This 1,607 square foot home was built in 1908.

Currently zoned as a single family, the property features 5 bedrooms and 2 bathrooms above grade, with a finished basement that includes 2 additional bedrooms and 1 bathroom. The first floor offers 3 bedrooms and 1 bathroom and has been recently updated with fresh paint and refinished flooring. The second floor includes 2 bedrooms, 1 bathroom, a full kitchen, and separate front and rear entrances, making it ideal for extended living arrangements. Additional features include an enclosed rear staircase, a roof that is approximately 2 years old, and a well maintained boiler. Great opportunity for an investor or owner occupant looking for space and value

Single Family Active

Price

^$ 140,000

Bedrooms

Full Bath

Property Type

Single Family

Taxes

^$ 738

Style

Year Built

1908

Town/City

Chicago

County/Region

Cook

MLS | Web ID

12600641

Features

General

Living Area 1607

Sewer Public Sewer

Heating Radiator(s)

Cooling Window Unit(s)

Possession Closing

Association Fee Includes None

Construction Materials Vinyl Siding

Year Built 1908

Township Lake

Tax Year 2023

Ownership Fee Simple

Assoc Fee Paid Per Not Applicable

County Cook

New Construction N

Property Type Residential Detached Single

Total Rooms 9

Full Baths 2

Status New

Directions Take Winchester Ave south to 59th ave and till the property

City Chicago

High School District 299

MLS Area CHI - West Englewood

Tax Annual Amount 738

Standard Status Active

Middle/Junior School District 299

Elementary School District 299

Interior

Basement Finished Full

Half Baths 0

Total Bedrooms 4

Room Type Bedroom 5

Total Baths 2

Bedrooms Possible 5

Exterior

Water Source Public

Total Parking 0

Lot Dimensions 25x125

Waterfront Y/N N

* Excluded Features

List By

Exp Realty

Broker

mauricio@cobblestonerealtygroup.com

Affordability Calculator

$924

Per Month

Monthly Principal & Interest: $862
Monthly Property Taxes: $62
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends
Schools

Single family listings in Chicago, IL

Average List Price ^$569,307

Percent of Sale Price 307%

About Chicago, IL

2,755,380 Population

-4% Since 2002

^$53,088 Median Income

36.07 Median Age

25% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

566059 Elementary School

566846 Middle School

Unknown High School High School

See complete school information

Pricing History

Date	Price	Price Change	Description
3/24/2026	$140,000		Listed Price

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5958 S Winchester Avenue, Chicago, IL, 60636 is a Single Family Home for sale at $140,000 with 1,607 sqft. 5958 S Winchester Avenue has 5 bedrooms, 2.0 baths, and was built in 1908. The property's zip code is 60636 which is in Chicago, IL

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Weichert Realtors are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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Data is updated as of 3/25/2026.

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5958 S Winchester Avenue

Single Family Home for sale in Chicago, IL

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