View 1159 Chatfield Road Winnetka, IL MLS# 12585208
$2,245,000
5

Beds

4.1

Baths

4,390

Sq.Ft.

1159 Chatfield Road

Winnetka, IL

MRED
Courtesy of COMPASS
View 1423 Asbury Avenue Winnetka, IL MLS# 12482150
$2,299,000
6

Beds

5.2

Baths

5,350

Sq.Ft.

1423 Asbury Avenue

Winnetka, IL

MRED
Courtesy of COMPASS
View 747 Lincoln Avenue Winnetka, IL MLS# 12645391
  • Recently Listed
1 of 54
$2,395,000
4

Beds

3.2

Baths

747 Lincoln Avenue

Winnetka, IL

MRED
Courtesy of @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 1185 Hill Road Winnetka, IL MLS# 12580255
$2,439,000
4

Beds

5.2

Baths

4,269

Sq.Ft.

1185 Hill Road

Winnetka, IL

MRED
Courtesy of COMPASS
View 1241 ASH Street Winnetka, IL MLS# 12608265
$2,489,000
5

Beds

5.1

Baths

4,680

Sq.Ft.

1241 ASH Street

Winnetka, IL

MRED
Courtesy of COMPASS
View 845 Glen Oak Drive Winnetka, IL MLS# 12583662
$2,495,000
5

Beds

3.2

Baths

4,597

Sq.Ft.

845 Glen Oak Drive

Winnetka, IL

MRED
Courtesy of @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
View 406 Woodley Woods Winnetka, IL MLS# 12611829
  • Virtual Tour
1 of 50
$2,499,900
6

Beds

4.2

Baths

5,458

Sq.Ft.

406 Woodley Woods

Winnetka, IL

MRED
Courtesy of GREYSTONE REALTY
View 355 Linden Street Winnetka, IL MLS# 12587031
$2,500,000
5

Beds

4.1

Baths

5,184

Sq.Ft.

355 Linden Street

Winnetka, IL

MRED
Courtesy of COMPASS
View 62 Woodley Road Winnetka, IL MLS# 12637769
  • Recently Listed
1 of 43
$2,569,900
6

Beds

4.2

Baths

7,000

Sq.Ft.

62 Woodley Road

Winnetka, IL

MRED
Courtesy of @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
View 92 Indian Hill Road Winnetka, IL MLS# 12620950
$2,695,000
4

Beds

3.2

Baths

4,574

Sq.Ft.

92 Indian Hill Road

Winnetka, IL

MRED
Courtesy of @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
View 42 Woodley Road Winnetka, IL MLS# 12533727
  • Virtual Tour
1 of 73
$2,750,000
4

Beds

3.3

Baths

4,225

Sq.Ft.

42 Woodley Road

Winnetka, IL

MRED
Courtesy of @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
View 510 Provident Avenue Winnetka, IL MLS# 12573223
$2,799,388
6

Beds

5.1

Baths

510 Provident Avenue

Winnetka, IL

MRED
Courtesy of JOHN PARK
View 4 Indian Hill Road Winnetka, IL MLS# 12549096
$2,995,000
5

Beds

6.1

Baths

4 Indian Hill Road

Winnetka, IL

MRED
Courtesy of @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
View 127 Glenwood Avenue Winnetka, IL MLS# 12637128
  • Recently Listed
1 of 50
$2,995,000
6

Beds

4.1

Baths

6,900

Sq.Ft.

127 Glenwood Avenue

Winnetka, IL

MRED
Courtesy of COMPASS
View 100 Old Green Bay Road Winnetka, IL MLS# 12555408
$3,200,000
6

Beds

4.2

Baths

7,914

Sq.Ft.

100 Old Green Bay Road

Winnetka, IL

MRED
Courtesy of COMPASS
View Address not provided Winnetka, IL MLS# 12496129
$3,599,000
4

Beds

4.1

Baths

5,499

Sq.Ft.

Address not provided

Winnetka, IL

MRED
Courtesy of @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
View 140 Birch Street Winnetka, IL MLS# 12564836
$4,500,000
6

Beds

5.2

Baths

6,212

Sq.Ft.

140 Birch Street

Winnetka, IL

MRED
Courtesy of COMPASS
View 1128 Mt. Pleasant Road Winnetka, IL MLS# 12606067
  • Recently Listed with Virtual Tour
1 of 43
$4,500,000
6

Beds

6.3

Baths

6,950

Sq.Ft.

1128 Mt. Pleasant Road

Winnetka, IL

MRED
Courtesy of @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
View 231 Woodlawn Avenue Winnetka, IL MLS# 12638690
$4,699,000
6

Beds

6.3

Baths

6,000

Sq.Ft.

231 Woodlawn Avenue

Winnetka, IL

MRED
Courtesy of STONE REALTY GROUP
View 32 Woodley Road Winnetka, IL MLS# 12283033
$4,950,000
5

Beds

4.3

Baths

9,908

Sq.Ft.

32 Woodley Road

Winnetka, IL

MRED
Courtesy of @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE

About Winnetka

Listings in Winnetka, IL

43

Estimated median home price

$2,299,000
Winnetka IL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winnetka, Illinois real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winnetka, IL.

Homes for Sale by Price in Winnetka, IL

Price Count
$0 - 100K 0
$100K - 200K 0
$200K - 300K 1
$300K - 400K 0
$400K - 500K 0
$500K - 600K 0
$600K - 700K 0
$700K - 800K 0
$800K - 900K 1
$900K - 1M 2
$1M - Max 39

Homes for Sale by Type in Winnetka, IL

Property Type Count
Single Family 41
Townhouse 0
Condo 1
Commercial 0
Rental 9
Lots and Land 1
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 5/14/2026)

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 5/14/2026.