7837 S Winchester Avenue
Chicago, IL, 60620
$289,900
4 Beds
2 Baths
0 SqFt
0 Acres
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$289,900
7837 S Winchester Avenue
Chicago, IL, 60620
MLS #MRD12605788 image #0MLS #MRD12605788 image #1MLS #MRD12605788 image #2MLS #MRD12605788 image #3MLS #MRD12605788 image #4MLS #MRD12605788 image #5MLS #MRD12605788 image #6MLS #MRD12605788 image #7MLS #MRD12605788 image #8MLS #MRD12605788 image #9MLS #MRD12605788 image #10MLS #MRD12605788 image #11MLS #MRD12605788 image #12MLS #MRD12605788 image #13
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
Beds:
4
Baths:
2
Type:
Multi Family
Neighborhood:
chiauburngresham
Listed Date:
Apr 2, 2026
Year Built:
1926
Chi – Auburn GreshamChiauburngresham

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
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Debra Dobbs is one of Chicago’s top realtors with more than 41 years in the real estate business.

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Current real estate data for Multi Family in Chicago as of Apr 06, 2026
1,327
Multi Family Listed
82
Avg DOM
$507,238
Avg List Price

Community

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Property Summary

    7837 S Winchester Avenue Chicago IL is a Multi Family for sale in Chicago, IL, 60620. It is listed for $289,900 To schedule a showing of MLS#mrd12605788 at 7837 S Winchester Avenue in Chicago, IL, contact your Compass | Debra Dobbs | The Dobbs Group agent at 3123074909.
7837 S Winchester Avenue
Chicago, IL