7837 S Winchester AVE Chicago, IL 60620 Open Sun 1PM-3PM

UPDATED: 04/02/2026 08:09 PM ON MARKET: 3 days on market

$289,900

4 Beds2 Baths

Key Details

Property Type Multi-Family

Sub Type Two to Four Units

Listing Status Active

Purchase Type For Sale

MLS Listing ID 12605788

Bedrooms 4

Year Built 1926

Annual Tax Amount $1,484

Tax Year 2023

Lot Dimensions 25x125

Property Sub-Type Two to Four Units

Location

State IL

County Cook

Area Chi - Auburn Gresham

Rooms

Basement Unfinished,Full

Interior

Heating Natural Gas,Steam

Fireplace N

Exterior

Roof Type Flat

Building

Dwelling Type Two to Four Units

Building Description Brick, No

Sewer Public Sewer

Water Lake Michigan,Public

Structure Type Brick

New Construction false

Schools

School District 299 ,299, 299

Others

Ownership Fee Simple

Special Listing Condition None

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.