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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.
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
Monthly Cost Estimate
$1,550/mo
20% down · 6.5% · 30 years
Estimates only. Actual payments may vary.
Location
7837 S Winchester Avenue
Chicago, IL 60620
Property Details
Construction
Parking
Heating
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.



















