5529 S Winchester Avenue Chicago, IL ^$ 160,000

5529 S Winchester Avenue

^$ 160,000

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5529 S Winchester Avenue

Chicago, IL, 60636

^$ 160,000

Bedrooms6 Baths2.0

Monthly Estimate*

^$ 1,105

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Multi-Family Home for sale in Chicago, IL

for $160,000 with 6 bedrooms and 2 full baths. This home was built in 1910 on a lot size of 0.09.

Looking for your next investment project in West Englewood? This all-brick two-flat features two units, each with 3 bedrooms and 1 bathroom, plus a full basement with additional space for storage, a workshop, or future improvements. Whether you're an investor looking to renovate both units or a buyer interested in living in one unit while renting the other, this property offers plenty of possibilities. With some vision and the right updates, you can make this property your own and explore its potential. Bring your contractor, take a look, and see what you can do with this West Englewood two-flat. **Schedule your showing today!** Sold AS-IS

Multi-Family Active

Price

^$ 160,000

Bedrooms

Full Bath

Property Type

Multi-Family

Taxes

^$ 2,021

Style

Lot Size

0.09

Year Built

1910

Town/City

Chicago

County/Region

Cook

MLS | Web ID

12770653

Features

General

Sewer Public Sewer

Heating Natural Gas

Possession Immediate

Roof Tar/Gravel

Garage Spaces 2

Construction Materials Brick

Year Built 1910

Township Lake

Tax Year 2025

Ownership Fee Simple

County Cook

New Construction N

Property Type Residential Income Two to Four Units

Total Rooms 6

Status New

Directions Take 55th St (Garfield Boulevard) West on Garfield then go South on Winchester Ave. then to property.

City Chicago

High School District 299

MLS Area CHI - West Englewood

Tax Annual Amount 2021.5

Standard Status Active

Middle/Junior School District 299

Elementary School District 299

Interior

Basement Unfinished Full

Total Bedrooms 6

Total Baths 2

Bedrooms Possible 6

Full Baths Building 2

Half Baths Building 0

Total Number of Units 2

Exterior

Parking Features Yes Garage Owned Detached Garage

Water Source Lake Michigan Public

Total Parking 2

Lot Dimensions 3720

Lot Size Acres 0.09

Waterfront Y/N N

* Excluded Features

List By

Century 21 Impact

Broker

khayyansells@gmail.com;khayyansells@gmail.com

Affordability Calculator

$1,273

Per Month

Monthly Principal & Interest: $1,105
Monthly Property Taxes: $168
Monthly Home Insurance: --

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Loan Term

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Yearly Home Insurance

Default based on a 30-year fixed rate of 7.375% 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

Multi-family listings in Chicago, IL

Average List Price ^$639,246

Percent of Sale Price 300%

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
10/12/2026	$160,000		Listed Price

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5529 S Winchester Avenue, Chicago, IL, 60636 is a Multi-Family Home for sale at $160,000 with a lot size of 0.09. 5529 S Winchester Avenue has 6 bedrooms, 2.0 baths, and was built in 1910. 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 7.375% 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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Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Data is updated as of 10/13/2026.

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5529 S Winchester Avenue

Multi-Family Home for sale in Chicago, IL

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