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Winnetka

Nestled along the North Shore, Winnetka is a community of tree-lined streets, sandy beaches, great schools, outstanding parks, and quality recreation facilities. Founded in 1869, Winnetka is a historic, family-oriented neighborhood with small-town charm and a thriving village for people to live and work. The community is located less than 20 miles north of the City of Chicago.

View The Market Report

Available Homes in Winnetka

1159 Chatfield RD, Winnetka, IL 60093
Open Sat 11AM-1PM
48

$2,245,000

5 Beds 4.5 Baths 4,390 SqFt

1159 Chatfield RD, Winnetka, IL 60093

Listed by Jason Rowland of Compass

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
92 Indian Hill RD, Winnetka, IL 60093
New
36

$2,695,000

4 Beds 4 Baths 4,574 SqFt

92 Indian Hill RD, Winnetka, IL 60093

Listed by Kathryn Mangel of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
1505 Tower RD, Winnetka, IL 60093
Active Under Contract
33

$995,000

4 Beds 4 Baths 3,225 SqFt

1505 Tower RD, Winnetka, IL 60093

Listed by Bonnie Tripton of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
556 Willow RD, Winnetka, IL 60093
Active Under Contract
43

$1,869,000

5 Beds 4.5 Baths 4,023 SqFt

556 Willow RD, Winnetka, IL 60093

Listed by Kathryn Moor of Compass

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
915 Sunset RD, Winnetka, IL 60093
New
23

$16,900,000

6 Beds 9 Baths 15,000 SqFt

915 Sunset RD, Winnetka, IL 60093

Listed by Mary Maris of Village Realty Group Inc

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
Winnetka, IL 60093
Active Under Contract
55

$1,495,000

4 Beds 3 Baths

Winnetka, IL 60093

Listed by Emily Smart LeMire of Compass

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
1523 Tower RD, Winnetka, IL 60093
Active Under Contract
29

$1,095,000

4 Beds 3 Baths 2,503 SqFt

1523 Tower RD, Winnetka, IL 60093

Listed by Mary Grant of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
995 Oak ST, Winnetka, IL 60093
Active Under Contract
38

$1,699,000

4 Beds 4.5 Baths 3,639 SqFt

995 Oak ST, Winnetka, IL 60093

Listed by Joanne Hudson of Compass

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
1255 Forest Glen DR N, Winnetka, IL 60093
Active Under Contract
36

$2,175,000

5 Beds 4 Baths 4,214 SqFt

1255 Forest Glen DR N, Winnetka, IL 60093

Listed by Bonnie Tripton of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
406 Woodley Woods, Winnetka, IL 60093
Active
50

$2,499,900

6 Beds 5 Baths 5,458 SqFt

406 Woodley Woods, Winnetka, IL 60093

Listed by Jason Wagner of Greystone Realty

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
91 ABBOTTSFORD RD, Winnetka, IL 60093
Active Under Contract
34

$1,895,000

5 Beds 4.5 Baths 5,231 SqFt

91 ABBOTTSFORD RD, Winnetka, IL 60093

Listed by Laura Fitzpatrick of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
574 Orchard LN, Winnetka, IL 60093
Active Under Contract
24

$899,000

3 Beds 2.5 Baths 6,599 Sqft Lot

574 Orchard LN, Winnetka, IL 60093

Listed by Danielle Wylie of Baird & Warner

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
841 Prospect AVE, Winnetka, IL 60093
Active Under Contract
35

$1,450,000

5 Beds 3.5 Baths

841 Prospect AVE, Winnetka, IL 60093

Listed by Christie Ascione of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
180 Westview RD, Winnetka, IL 60093
Active Under Contract
38

$1,850,000

3 Beds 2.5 Baths 4,356 SqFt

180 Westview RD, Winnetka, IL 60093

Listed by Cody McGuire of @properties Commercial

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
373 Sunset RD, Winnetka, IL 60093
Active Under Contract
26

$1,439,000

5 Beds 3.5 Baths 3,465 SqFt

373 Sunset RD, Winnetka, IL 60093

Listed by Joanne Hudson of Compass

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
555 Hill TER #307, Winnetka, IL 60093
Active Under Contract
20

$300,000

1 Bed 1 Bath 760 SqFt

555 Hill TER #307, Winnetka, IL 60093

Listed by Celia Nelson of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
140 Birch ST, Winnetka, IL 60093
Active Under Contract
78

$4,500,000

6 Beds 6 Baths 6,212 SqFt

140 Birch ST, Winnetka, IL 60093

Listed by Julie Miller of Compass

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
918 Green Bay RD #3G, Winnetka, IL 60093
Active
15

$2,045

1 Bed 1 Bath 750 SqFt

918 Green Bay RD #3G, Winnetka, IL 60093

Listed by Renee Pehanich of Fulton Grace Realty

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
733 Elm ST #302, Winnetka, IL 60093
Active
10

$1,995

1 Bed 1 Bath 700 SqFt

733 Elm ST #302, Winnetka, IL 60093

Listed by Renee Pehanich of Fulton Grace Realty

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
733 Elm ST #301, Winnetka, IL 60093
Active
7

$1,745

1 Baths 500 SqFt

733 Elm ST #301, Winnetka, IL 60093

Listed by Renee Pehanich of Fulton Grace Realty

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
979 Vine ST, Winnetka, IL 60093
Active
35

$950,000

4 Beds 1.5 Baths 2,100 SqFt

979 Vine ST, Winnetka, IL 60093

Listed by Vernon Ewing Spence of Jason Mitchell Real Estate IL

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
845 Glen Oak DR, Winnetka, IL 60093
Active Under Contract
26

$2,495,000

5 Beds 4 Baths 4,597 SqFt

845 Glen Oak DR, Winnetka, IL 60093

Listed by Kathryn Mangel of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
838 Lincoln AVE, Winnetka, IL 60093
Pending
42

$1,739,000

5 Beds 4 Baths 3,162 SqFt

838 Lincoln AVE, Winnetka, IL 60093

Listed by Joanne Hudson of Compass

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
174 Woodland AVE, Winnetka, IL 60093
Active Under Contract
26

$1,399,000

3 Beds 2.5 Baths 3,248 SqFt

174 Woodland AVE, Winnetka, IL 60093

Listed by Marlene Rubenstein of Baird & Warner

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX

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 Blok are marked with the Broker Reciprocity thumbnail logo and detailed information about them includes the name of the listing brokerage. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Digital Millennium Copyright Act – DMCA Notice Based on information submitted to the MLS GRID as of 04/23/2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal non-commercial use, it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, the data is deemed reliable but is not guaranteed by MLS GRID, the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time. MLS GRID may, at its discretion, require use of other disclaimers as necessary to protect Member Participant, and/or their MLS from liability. Data last updated: 04/23/2026.

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    © 2026 The Matlin Group | LIC #475.158591 | Compass - All rights reserved | Privacy Policy | DMCA Policy | Powered by Blok.

    The Matlin Group is a real estate team affiliated with Compass, a licensed real estate broker and abides by all applicable Equal Housing Opportunity laws. All material presented herein is intended for informational purposes only. Information is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to accuracy of any description. All measurements and square footages are approximate. This is not intended to solicit property already listed. Some or all of the listings may not belong to the firm whose website is being visited. Nothing herein shall be construed as legal, accounting or other professional advice outside the realm of real estate brokerage.

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