Winnetka, IL Single Family Homes For Sale

Curated by Liz Finks. Last updated March 3
Homes for sale in Winnetka, IL, offer an unparalleled blend of rich history, modern amenities, and access to stunning natural beauty. The village features a variety of historic homes, alongside new residential and commercial development, including the popular Plaza del Lago—an upscale shopping center with unique boutiques and local dining options. Tower Beach, with its pristine lakefront access, is a standout feature, providing residents a private retreat to enjoy Lake Michigan’s beauty. Winnetka’s exceptional public schools, including the highly ranked New Trier High School, make it a top destination for families. Its proximity to downtown Chicago—just 14 miles north—provides seamless access to the city via Metra or major highways, blending the peace of suburban life with the convenience of urban living. The community is vibrant and dynamic, offering residents a range of recreational opportunities, from the expansive Winnetka Park District to cultural events hosted year-round. With its prime location, excellent schools, and attractive local amenities, Winnetka presents an ideal environment for both homebuyers and investors seeking long-term value and a high quality of life.
1/63
Pending

$11,999,900

7
Bedrooms
15,784
Square Feet
1.3
Acres

765 Sheridan Road, Winnetka, IL 60093

1/25
Compass Coming Soon

$3,999,000

7
Bedrooms
8,839
Square Feet
0.61
Acres

945 Pine Tree Lane, Winnetka, IL 60093

1/70
ContingentVirtual Tour

$2,490,000

7
Bedrooms
5,400
Square Feet
0.19
Acres

747 Walden Road, Winnetka, IL 60093

$4,500,000 | 35 Indian Hill Road, Winnetka, IL 60093
Closed 4/18/25

$4,500,000

7
Bedrooms
9,744
Square Feet
Unavailable
Acres

35 Indian Hill Road, Winnetka, IL 60093

a view of a house with a yard
1/21

$892,500

4
Bedrooms
1,355
Square Feet
0.11
Acres

979 Vine Street, Winnetka, IL 60093

a utility room with washer and dryer
1/36
Listed By CompassContingent

$2,675,000

6
Bedrooms
4,251
Square Feet
0.42
Acres

474 Sheridan Road, Winnetka, IL 60093

a view of a building with a yard
Closed 4/7/25

$2,200,000

5
Bedrooms
4,381
Square Feet
0.19
Acres

529 Elder Lane, Winnetka, IL 60093

$5,250,000 | 66 Fox Lane, Winnetka, IL 60093
1/44
Pending

$5,250,000

6
Bedrooms
8,025
Square Feet
0.93
Acres

66 Fox Lane, Winnetka, IL 60093

$2,600,000 | 1172 Hamptondale Avenue, Winnetka, IL 60093
1/2
Closed 4/9/25

$2,600,000

5
Bedrooms
4,870
Square Feet
0.38
Acres

1172 Hamptondale Avenue, Winnetka, IL 60093

$1,100,000 | 886 Willow Road, Winnetka, IL 60093
1/35
Contingent

$1,100,000

4
Bedrooms
2,534
Square Feet
0.15
Acres

886 Willow Road, Winnetka, IL 60093

$2,675,000 | 332 Elder Lane, Winnetka, IL 60093
1/59
Closed 5/12/25

$2,675,000

7
Bedrooms
6,102
Square Feet
0.48
Acres

332 Elder Lane, Winnetka, IL 60093

an aerial view of a house with yard swimming pool and outdoor seating
1/73
Compass Coming Soon

$5,200,000

6
Bedrooms
6,639
Square Feet
1.7
Acres

22 Indian Hill Road, Winnetka, IL 60093

$3,900,000 | 865 Gordon Terrace, Winnetka, IL 60093
1/71
Closed 5/14/25

$3,900,000

5
Bedrooms
9,350
Square Feet
0.38
Acres

865 Gordon Terrace, Winnetka, IL 60093

a front view of a house
1/82
Closed 4/22/25

$1,650,000

5
Bedrooms
3,377
Square Feet
0.27
Acres

705 Oak Street, Winnetka, IL 60093

a front view of a residential apartment building with a yard
1/71

$4,499,900

8
Bedrooms
7,168
Square Feet
1.46
Acres

5 Woodley Road, Winnetka, IL 60093

a view of a house with a yard
1/50
Listed By Compass

$2,290,000

5
Bedrooms
4,460
Square Feet
0.19
Acres

803 Pine Street, Winnetka, IL 60093

$4,950,000 | 32 Woodley Road, Winnetka, IL 60093
1/55

$4,950,000

5
Bedrooms
9,908
Square Feet
1.9
Acres

32 Woodley Road, Winnetka, IL 60093

a front view of a house with garden
1/16
Closed 5/1/25

$1,500,000

4
Bedrooms
3,000
Square Feet
0.21
Acres

965 Spruce Street, Winnetka, IL 60093

$930,000 | 214 Poplar Street, Winnetka, IL 60093
1/46
Closed 4/14/25

$930,000

3
Bedrooms
Unavailable
Square Feet
0.14
Acres

214 Poplar Street, Winnetka, IL 60093

$4,650,000 | 90 Locust Road, Winnetka, IL 60093
1/55
Listed By Compass

$4,650,000

6
Bedrooms
Unavailable
Square Feet
Unavailable
Acres

90 Locust Road, Winnetka, IL 60093