For Sale
Multi family home for sale at 5529 S Winchester Ave, Chicago, IL 60636 | MLS# 12770653 | Listing updated on 2026-10-18
Photo 1 of Multi family home for sale at 5529 S Winchester Ave, Chicago, IL 60636 | MLS# 12770653 | Listing updated on 2026-10-18
Photo 2 of Multi family home for sale at 5529 S Winchester Ave, Chicago, IL 60636 | MLS# 12770653 | Listing updated on 2026-10-18
Photo 3 of Multi family home for sale at 5529 S Winchester Ave, Chicago, IL 60636 | MLS# 12770653 | Listing updated on 2026-10-18
Photo 4 of Multi family home for sale at 5529 S Winchester Ave, Chicago, IL 60636 | MLS# 12770653 | Listing updated on 2026-10-18
18+
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Street View

$160,000

Monthly Est:$796

  • Beds Icon5 Beds
  • Beds Icon
    2 Baths
  • Beds Icon--sqft

5529 S Winchester Ave, Chicago, IL 60636

$796/moEst:

Get Pre-Approved

  • Multi Family

  • Built in 1910

  • $-- HOA

  • 3,920.4 sqft lot

  • --/sqft

Description

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. Great ARV Upside in this area. **Schedule your showing today!** Sold AS-IS

  • Houzeo last checked: 11 minutes ago
  • Listing updated: October 18, 2026 at 5:12 pm
  • Listing Provided by: Khayyan Valentine-Johnson , Jaiva Birch DRE #475179938 | Century 21 IMPACT (815) 221-8400
  • Source: MRED MLS-IL | MLS#: 12770653 MRED MLS-IL

Part of

Building
5529 S Winchester Ave
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Property Details

  • Status

    Active

  • Type

    Multi Family

  • No. of Stories

    -

  • County

    Cook County

  • City

    Chicago

  • Neighborhood

    West Englewood

  • Year Built

    1910

  • HOA Fees

    -

  • Finished Area

    - sqft

  • Lot Size

    3,920.4 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    MRED MLS

  • MLS Number

    12770653

  • MLS Status

    Active

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 5

    Bathrooms: 2

Interior

  • Heating

    Natural Gas

  • Sewer

    Public Sewer

Construction

  • Year Built

    Year Built: 1910

  • Home type

    Multi Family

  • Construction Materials

    Brick

  • Roof

    Tar/gravel

Utilities & Energy

  • Water Source

    Lake Michigan, Public

  • Basement

    Unfinished, Full

  • Parking Features

    Yes, Garage Owned, Detached, Garage

West Englewood Ranks #180 in Chicago, IL

Homes for sale
222

Homes

Rental prices
$1,065

Rental Prices

Median Home Price
$165K

Median Home Price

West Englewood, Chicago, IL neighborhood guide

Getting Around 5529 S Winchester Ave

Bike Score®

Bike Score

Bikeable

62/100

Walk Score®

Walk Score

Somewhat Walkable

67/100

Transit Score®

Transit Score

Good Transit

61/100

Data provided by Redfin

Nearby Homes

This representation is based in whole or in part on data supplied by Midwest Real Estate Data, LLC through Oct 20, 2026, 05:15AM. Midwest Real Estate Data, LLC does not guarantee nor is it in any way responsible for its accuracy. Data maintained by Midwest Real Estate Data LLC may not reflect all real estate activity in the market.

Based on information submitted to the MLS GRID as of Oct 20, 2026, 05:15AM. All data is obtained from various sources and has not been, and will not be, verified by broker or MLS GRID. Supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. This website may not include listings or property addresses of sellers who have directed their listing brokers to withhold their listing or their property address from display on the Internet. Some IDX listings have been excluded from this website. Information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID, MRED or Houzeo. The use of the MLS GRID Data may be subject to an end user license agreement. Properties displayed may be listed or sold by various participants in the MLS,

Listings courtesy of MRED as distributed by MLS GRID. ©2026 Midwest Real Estate Data LLC. All Rights Reserved

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