View 5014 S Paulina Street Chicago, IL MLS# 12548583
$249,900
5

Beds

3.0

Baths

5014 S Paulina Street

Chicago, IL

MRED
Courtesy of SU FAMILIA REAL ESTATE INC
View 6403 S Lorel Avenue Chicago, IL MLS# 12578568
  • Recently Listed
1 of 28
$249,900
2

Beds

1.1

Baths

891

Sq.Ft.

6403 S Lorel Avenue

Chicago, IL

MRED
Courtesy of CROSSTOWN REALTORS, INC.
View 5431 S Natoma Avenue Chicago, IL MLS# 12576090
$249,900
5

Beds

2.0

Baths

1,041

Sq.Ft.

5431 S Natoma Avenue

Chicago, IL

MRED
Courtesy of TORG REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 5929 S Major Avenue Chicago, IL MLS# 12580592
  • Recently Listed
1 of 5
$249,900
3

Beds

1.0

Baths

900

Sq.Ft.

5929 S Major Avenue

Chicago, IL

MRED
Courtesy of DOUBLE TT REAL ESTATE INC.
View 2223 W 50th Place Chicago, IL MLS# 12577844
$249,990
6

Beds

3.0

Baths

2,400

Sq.Ft.

2223 W 50th Place

Chicago, IL

MRED
Courtesy of SHOPPING CASAS CHICAGO LLC
View 3624 S Paulina Street Chicago, IL MLS# 12418428
$250,000
4

Beds

2.0

Baths

3624 S Paulina Street

Chicago, IL

MRED
Courtesy of INFINITI PROPERTIES, INC.
View 4452 S Lawler Avenue Chicago, IL MLS# 12573408
$250,000
3

Beds

2.0

Baths

1,008

Sq.Ft.

4452 S Lawler Avenue

Chicago, IL

MRED
Courtesy of CENTURY 21 CIRCLE
View 5638 S Maplewood Avenue Chicago, IL MLS# 12549874
$251,000
3

Beds

2.0

Baths

1,400

Sq.Ft.

5638 S Maplewood Avenue

Chicago, IL

MRED
Courtesy of PMJ REALTY
View 3750 W 65th Street Chicago, IL MLS# 12577156
  • Recently Listed
1 of 14
$254,999
5

Beds

2.0

Baths

1,035

Sq.Ft.

3750 W 65th Street

Chicago, IL

MRED
Courtesy of REALTY OF AMERICA, LLC
View 3535 S Damen Avenue Chicago, IL MLS# 12524753
$259,000
1

Beds

2.0

Baths

921

Sq.Ft.

3535 S Damen Avenue

Chicago, IL

MRED
Courtesy of KALE REALTY
View 2820 W 36th Street Chicago, IL MLS# 12404629
$259,900
5

Beds

2.0

Baths

1,783

Sq.Ft.

2820 W 36th Street

Chicago, IL

MRED
Courtesy of URBANITAS INC.
View 4857 S Lorel Avenue Chicago, IL MLS# 12582636
  • Recently Listed with Virtual Tour
1 of 23
$259,900
3

Beds

1.0

Baths

1,050

Sq.Ft.

4857 S Lorel Avenue

Chicago, IL

MRED
Courtesy of REALTY EXECUTIVES MIDWEST
View 1718 W 48th Street Chicago, IL MLS# 12481421
$260,000

1718 W 48th Street

Chicago, IL

MRED
Courtesy of NAIM LUXE REALTY LLC
View 5820 S Washtenaw Avenue Chicago, IL MLS# 12478352
$264,900
6

Beds

2.0

Baths

1,350

Sq.Ft.

5820 S Washtenaw Avenue

Chicago, IL

MRED
Courtesy of CITY LIFE REALTY
View 5434 S Union Avenue Chicago, IL MLS# 12305382
$265,000
3,800

Sq.Ft.

5434 S Union Avenue

Chicago, IL

MRED
Courtesy of COMPASS
View 3000 S WENTWORTH Avenue # 4B Chicago, IL MLS# 12539032
$265,000
2

Beds

2.0

Baths

910

Sq.Ft.

3000 S WENTWORTH Avenue # 4B

Chicago, IL

MRED
Courtesy of LAKESIDE PROPERTIES GROUP, LLC
View 5317 S Hamilton Avenue Chicago, IL MLS# 12549554
$265,000
3

Beds

1.0

Baths

960

Sq.Ft.

5317 S Hamilton Avenue

Chicago, IL

MRED
Courtesy of COLDWELL BANKER REALTY
View 5419 S HERMITAGE Avenue Chicago, IL MLS# 12581608
  • Recently Listed
1 of 14
$265,000
6

Beds

2.0

Baths

5419 S HERMITAGE Avenue

Chicago, IL

MRED
Courtesy of REAL ESTATE GROWTH PARTNERS
View 4629 S Ashland Avenue Chicago, IL MLS# 12535240
$265,900

4629 S Ashland Avenue

Chicago, IL

MRED
Courtesy of RE/MAX MI CASA
View 4002 S Western Avenue # 2 Chicago, IL MLS# 12567934
$268,000
3

Beds

2.0

Baths

1,277

Sq.Ft.

4002 S Western Avenue # 2

Chicago, IL

MRED
Courtesy of CENTURY 21 REALTY ASSOCIATES

About Southwest Side

Listings in Southwest Side, Chicago, IL

513

Estimated median home price

$349,900
Southwest Side, Chicago Real Estate

Search Southwest Side, Illinois Real Estate Listings & New Homes for Sale in Southwest Side, IL. Find Southwest Side Houses, Townhouses, Condos, & Properties for Sale at Weichert.com

Homes for Sale by Price in Southwest Side, Chicago, IL

PriceCount
$0 - 100K52
$100K - 200K52
$200K - 300K101
$300K - 400K140
$400K - 500K66
$500K - 600K37
$600K - 700K24
$700K - 800K10
$800K - 900K9
$900K - 1M4
$1M - Max18

Homes for Sale by Type in Southwest Side, Chicago, IL

Property TypeCount
Single Family220
Townhouse12
Condo48
Commercial52
Rental166
Lots and Land55
Condo/Town/CoOp0
CoOp0
Multi Family116
Mobile Home0
Farms1

(Data as of 3/5/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Weichert Realtors are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Copyright © 2026 Midwest Real Estate Data LLC.

Data is updated as of 3/5/2026.