118 total properties
View 1304 W Winona Street # 2 Chicago, IL MLS# 12601776
  • New Construction
1 of 31
$875,000
3

Beds

2.0

Baths

1,750

Sq.Ft.

1304 W Winona Street # 2

Chicago, IL

MRED
Courtesy of @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
View 4848 N Sheridan Road Chicago, IL MLS# 12627814
$899,000
5,257

Sq.Ft.

4848 N Sheridan Road

Chicago, IL

MRED
Courtesy of KAWASH GROUP
View 1470 W Winona Street # 102 Chicago, IL MLS# 12609846
$925,000
3

Beds

2.1

Baths

2,400

Sq.Ft.

1470 W Winona Street # 102

Chicago, IL

MRED
Courtesy of COMPASS
The time to sell is now! THE TIME TO SELL IS NOW!
View 968 W Cuyler Avenue Chicago, IL MLS# 12652181
  • Recently Listed
1 of 27
OPEN HOUSE: Sunday 5/31 12:00 PM - 2:00 PM
$925,000
3

Beds

2.1

Baths

2,650

Sq.Ft.

968 W Cuyler Avenue

Chicago, IL

MRED
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES CHICAGO
View 1657 W Winona Street Chicago, IL MLS# 12619438
  • Virtual Tour
1 of 26
$950,000
5

Beds

3.0

Baths

1657 W Winona Street

Chicago, IL

MRED
Courtesy of CL3 PROPERTY MANAGEMENT
View 832 W Junior Terrace Chicago, IL MLS# 12649588
$995,000
7

Beds

4.1

Baths

4,668

Sq.Ft.

832 W Junior Terrace

Chicago, IL

MRED
Courtesy of KELLER WILLIAMS ONECHICAGO
View 4612 N Magnolia Avenue Chicago, IL MLS# 12449994
$999,000
Studio

Beds

0.0

Baths

4612 N Magnolia Avenue

Chicago, IL

MRED
Courtesy of @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
View 4445-4447 N Broadway Avenue Chicago, IL MLS# 12383284
$1,200,000
5,146

Sq.Ft.

4445-4447 N Broadway Avenue

Chicago, IL

MRED
Courtesy of REAL PEOPLE REALTY
View 4422 N Clark Street Chicago, IL MLS# 12558581
$1,299,950
4,000

Sq.Ft.

4422 N Clark Street

Chicago, IL

MRED
Courtesy of EDWARD BOHRER
View 1655 W Carmen Avenue Chicago, IL MLS# 12642366
$1,700,000
5

Beds

4.1

Baths

3,800

Sq.Ft.

1655 W Carmen Avenue

Chicago, IL

MRED
Courtesy of COMPASS
View 740 W Hutchinson Street Chicago, IL MLS# 12604489
  • Virtual Tour
1 of 65
$1,899,000
6

Beds

4.1

Baths

5,610

Sq.Ft.

740 W Hutchinson Street

Chicago, IL

MRED
Courtesy of KELLER WILLIAMS ONECHICAGO
View 4844 N Hermitage Avenue Chicago, IL MLS# 12629882
  • New Construction
1 of 55
OPEN HOUSE: Sunday 5/31 12:30 PM - 1:30 PM
$2,249,000
6

Beds

4.1

Baths

4,800

Sq.Ft.

4844 N Hermitage Avenue

Chicago, IL

MRED
Courtesy of COMPASS
View 1235 W Foster Avenue Chicago, IL MLS# 12592954
$2,250,000
14

Beds

0.0

Baths

1235 W Foster Avenue

Chicago, IL

MRED
Courtesy of HOMESMART CONNECT LLC
View 1705 W Leland Avenue Chicago, IL MLS# 12590325
  • Virtual Tour
1 of 35
$2,395,000
7

Beds

6.1

Baths

4,807

Sq.Ft.

1705 W Leland Avenue

Chicago, IL

MRED
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES CHICAGO
View 4442 N Greenview Avenue Chicago, IL MLS# 12648483
  • Recently Listed
1 of 48
OPEN HOUSE: Sunday 5/31 11:00 AM - 1:00 PM
$2,475,000
6

Beds

4.1

Baths

4,560

Sq.Ft.

4442 N Greenview Avenue

Chicago, IL

MRED
Courtesy of COMPASS
View 4444 N Greenview Avenue Chicago, IL MLS# 12653158
  • Recently Listed
1 of 47
OPEN HOUSE: Sunday 5/31 11:00 AM - 1:00 PM
$2,475,000
6

Beds

4.1

Baths

4,560

Sq.Ft.

4444 N Greenview Avenue

Chicago, IL

MRED
Courtesy of COMPASS
View 4740 N Hermitage Avenue Chicago, IL MLS# 12583809
  • Virtual Tour
1 of 41
$2,499,000
6

Beds

5.1

Baths

4,925

Sq.Ft.

4740 N Hermitage Avenue

Chicago, IL

MRED
Courtesy of KELLER WILLIAMS ONECHICAGO
View 4841 N Hermitage Avenue Chicago, IL MLS# 12590432
$2,500,000
6

Beds

4.1

Baths

4,553

Sq.Ft.

4841 N Hermitage Avenue

Chicago, IL

MRED
Courtesy of JAMESON SOTHEBY'S INTL REALTY

About Uptown

Listings in Uptown, Chicago, IL

118

Estimated median home price

$425,000
Uptown, Chicago Real Estate

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

Homes for Sale by Price in Uptown, Chicago, IL

Price Count
$0 - 100K 2
$100K - 200K 19
$200K - 300K 23
$300K - 400K 12
$400K - 500K 21
$500K - 600K 14
$600K - 700K 3
$700K - 800K 5
$800K - 900K 3
$900K - 1M 5
$1M - Max 11

Homes for Sale by Type in Uptown, Chicago, IL

Property Type Count
Single Family 9
Townhouse 3
Condo 97
Commercial 4
Rental 60
Lots and Land 1
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 5/31/2026)

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 5/31/2026.