7837 S Winchester Avenue, Chicago, IL 60620

• 4 beds |
• 2 baths

Property 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.

Listing Status:

Active

Data Last Updated:

April 3, 2026 at 2:20AM

Listing Office:

Keller Williams ONEChicago : 312-589-0924

Listing Agent:

Jerome Harper : 312-589-0924

MLS ID:

12605788

Interior

• Basement: UnfinishedFull
• Heating: Natural GasSteam

Exterior

• Parking: Off AlleyAlley AccessYesOwnedParking spaces: 2

Construction

• Roofing: Flat
• General: Concrete Perimeter

Location

• Originating MLS: mred
• School District: 299
• County: Cook

Lot

• Zoning: 20304290130000

Utilities

• Water: Lake MichiganPublic
• Sewer: Public Sewer

Financial

• Source: mred
• Ownership: Fee Simple