Curious about this home?

Ask anything — no agents, no pressure

Try asking

About This Home

This 4-bedroom, 2-bathroom residential multi family at 7837 S Winchester Avenue in Chicago, IL is listed for $289,900. Built in 1926, on a N/A lot.

Agent Description

This well-maintained brick 2-flat in Auburn Gresham is exactly what smart buyers are looking for -- a chance to plant roots in an established neighborhood while building real wealth from day one. Live in one unit, rent the other, and let your tenant help cover your mortgage.

Built in 1926 and thoughtfully updated of the years, this solid Chicago two-flat offers 2,278 square feet of living space across two units, four bedrooms, and two full baths. The big-ticket items have already been addressed -- new roof, gutters, and tuckpointing completed in 2025, along with updated flooring throughout.

The full unfinished basement has good ceiling height, giving a future owner real options for additional living space, or storage. The boiler is 12 years old, functional and well maintained. Auburn Gresham is a neighborhood with deep roots and a strong sense of community, close to public transit, local dining, and everything the South Side has to offer. For the buyer who wants more than a house and is looking for a real asset, this one is worth a close look.

Key Features

  • Built in 1926
  • 2 parking spaces

Property Details

2 full
2 spaces
1926

Monthly Cost Estimate

$1,550/mo

20% down · 6.5% · 30 years

Principal$210
Interest$1,256
Insurance$85

Estimates only. Actual payments may vary.

Location

7837 S Winchester Avenue

Chicago, IL 60620

Property Details

Construction

Brick

Parking

AlleyOwnedOff Alley

Heating

Natural GasSteam

Questions & Answers

This 4-bedroom, 2-bathroom residential multi family at 7837 S Winchester Avenue is listed at $289,900. The estimated monthly payment is $1,256 based on 20% down at 6.5% interest.

Key features include: Built in 1926, 2 parking spaces.

This property is listed by Jerome Harper and can be reached at (312) 216-2422 or jerome@thecollectivechicago.com.

Similar Homes in Chicago

View all
JH

Jerome Harper

Agent at Keller Williams ONEChicago

(312) 216-2422

Listed by Keller Williams ONEChicago

MLS# 12605788· Source: listhub· Updated 8 days ago

Copyright © 2026 Midwest Real Estate Data, LLC. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

7837 S Winchester Avenue, Chicago, IL 60620

Open this listing in: