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.
Property Details
Price:
$289,900
MLS #:
MRD12605788
Status:
Active Under Contract
Beds:
4
Baths:
2
Type:
Multi Family
Neighborhood:
chiauburngresham
Listed Date:
Apr 2, 2026
Year Built:
1926
See this Listing
Schools
School District:
299
Interior
Heating
Natural Gas, Steam
Exterior
Construction Materials
Brick
Parking Features
Off Alley, Alley Access, Yes, Owned
Parking Spots
2
Parking Total
2
Roof
Flat
Financial
Tax Year
2023
Taxes
$1,484
Map
Community
- Address7837 S Winchester Avenue Chicago IL
- CityChicago
- CountyCook
- Zip Code60620
Market Summary
Current real estate data for Multi Family in Chicago as of Jun 16, 2026
1,396
Multi Family Listed
80
Avg DOM
$531,359
Avg List Price
Property Summary
- 7837 S Winchester Avenue Chicago IL is a Multi Family for sale in Chicago, IL, 60620. It is listed for $289,900
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Copyright 2026. All rights reserved.
7837 S Winchester Avenue
Chicago, IL


