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18 Properties Within 0.5 miles of: 7837 S Winchester, Chicago

7837 S Winchester
Chicago, IL 60620

  • 4 Beds
  • Built In 1926
Price

$289,900

Est Payment
$1,583 / month (details)  
Taxes
$1,484  
Beds
4  
Rooms
10  
Type
Two to Four Units  
Sq. Ft.
n/a  
Lot Size
25x125  
Built
1926  
Neighborhood
Gresham  
MLS
#12605788
Status
Active (0 days)

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.

Property Map

Property Details

Utilities

  • Heating Natural Gas, Steam
  • Cooling
  • Water Lake Michigan, Public
  • Sewer Public Sewer

Additional Information

Parking
2 Parking Spaces, Off Alley, Alley Access, Yes, Owned
Schools
District 299

Payment Calculator

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Principal & Interest
$0
Property Tax
$0
Assessments
$0
Home Insurance
$0
Mortgage Insurance
$0

Listing History

04-02-2026 Listed at $289,900
Last Modified 4/2/26 3:08 PM

Nearby Transportation

  • Bus 79 < 0.1 mi
  • Bus 48 0.1 mi
  • Bus 169 0.4 mi
  • Bus 9 0.4 mi
  • Bus X9 0.4 mi
  • Bus X49 0.6 mi
  • Bus 49 0.6 mi
  • Bus 75 0.6 mi
  • Bus 94 0.6 mi
  • Bus 44 0.9 mi
  • Bus 95 1.0 mi
  • Bus 87 1.0 mi
  • Bus 67 1.1 mi
  • I 94 East 2.3 mi
  • I 94 West 2.4 mi
  • Hwy 57 2.8 mi
  • Hwy 57 2.9 mi
  • I 90 East 2.9 mi
  • I 90 West 3.0 mi
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