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$289,900 Just Listed

  • For Sale
  • Active
  • Multi-Family
  • 4 Total Beds
  • Updated 4 hours ago

Next open house:

Open House: 11:00 AM - 1:00 PM

Saturday 4/4 11:00 AM - 1:00 PM

7837 S Winchester Avenue,Chicago, IL 60620

7837 S Winchester AvenueChicagoIL60620

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  • Open House: 1:00 PM - 3:00 PM

    Sunday 4/5 1:00 PM - 3:00 PM

    7837 S Winchester Avenue,Chicago, IL 60620
    7837 S Winchester AvenueChicagoIL60620
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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.

Full Property Details for 7837 S Winchester Ave

General

  • Price: $289,900
  • Taxes: $1,484 (2023)
  • Status: Active
  • Type: Multi-Family
  • Source: MRED
  • MLS ID: 12605788
  • Updated: Today (4/2/2026)
  • Added to Site: Today

Interior

  • Basement: Unfinished

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Upper - Full Baths: 2

Bedrooms

  • Total Bedrooms: 4

Parking

  • Total Spaces: 2
  • Parking Features: Off-Alley, Alley Access, Yes, Owned

Location

  • Area: CHI - Auburn Gresham
  • County: Cook
  • Township: South Chicago
  • Driving Directions: Take the 79th Street exit from I-94. Head west on 79th Street (away from the expressway). Continue straight for about 2.5-3 miles. Turn right (north) onto South Winchester Avenue. Drive about 0.2 miles (2-3 blocks). Arrive at 7837 South Winchester Avenue - it will be on your right-hand side.

School Information

  • School District: 299
  • Elem School District: 299
  • Midd School District: 299
  • High School District: 299

Heating & Cooling

  • Heating Type: Natural Gas, Steam

Utilities

  • Sewer: Public Sewer
  • Water: Lake Michigan, Public

Structural Information

  • Construction: Brick
  • Exterior Const.: Brick
  • Basement: Yes
  • Basement Desc.: Unfinished, Full
  • Foundation: Concrete Perimeter
  • Roof: Flat
  • Year Built: 1926
  • Built Before 1978: Yes

Unit Information

  • Units in Building: 2

Lot Features

  • Lot Size Range: Less than .25 Acre
  • Lot Dimensions: 25 x 125

Financial Considerations

  • Assessment Year: 1926
  • Tax Amount: $1,484
  • Tax Year: 2023
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Fee Simple
  • Property ID: 20304290130000

Listed by Keller Williams ONEChicago

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— 7837 S Winchester Ave —

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NMLS#: 1598647

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Save up to an additional 20% by bundling your home and auto together!

Schools serving 7837 S Winchester Ave

School District:Chicago Public School District 299
NameGradesDistance
Barton Elementary School, Chicago, IL
7650 South Wolcott Avenue, Chicago, IL 60620
PK-80.3 mi
Hirsch Metropolitan High School
7740 South Ingleside Avenue, Chicago, IL 60619
9-123.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 7837 S Winchester Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/02/2026
Listed
$289,900
866.33%
MLS
8/01/2011
Sold
$30,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 7837 S Winchester Ave

Year
Property Taxes
Change
Tax Assessment
Change
2023
$1,484
5%
$13,000
—
2022
$1,408
10%
$13,000
—
2021
$1,275
-3%
$13,000
-4%
2020
$1,317
—
$13,501
-12%
2019
$1,313
2%
$15,342
—
2018
$1,293
-7%
$15,342
-7%
2017
$1,384
-23%
$16,534
—
2016
$1,790
4%
$16,534
—
2015
$1,720
-33%
$16,534
19%
2014
$2,582
51%
$13,919
—
2013
$1,712
-1%
$13,919
—
2012
$1,730
—
$13,919
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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7837 S Winchester Avenue, Chicago, IL 60620 (MLS# 12605788) is a Multi-Family property with 2 units containing 4 bedrooms and 0 full bathrooms. 7837 S Winchester Avenue is currently listed for $289,900 and was received on April 02, 2026. Want to learn more about 7837 S Winchester Avenue? Do you have questions about finding other Multi-Family real estate for sale in Auburn Gresham? You can browse all Auburn Gresham real estate or contact a Coldwell Banker agent to request more information.

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