Highland Park, IL Single Family Homes For Sale

Curated by Liz Finks. Last updated March 3
Highland Park, IL, stands out for its rich history, diverse housing options, and strong sense of community. The neighborhood boasts a variety of amenities, including the vibrant downtown area with boutique shopping, top-tier dining, and year-round events. The popular Ravinia Festival, a beloved outdoor music venue, draws residents and visitors alike, offering a cultural experience that sets Highland Park apart. The community also features picturesque parks, including the stunning Rosewood Beach on Lake Michigan, ideal for outdoor enthusiasts. With highly regarded public and private schools, it's an excellent place for families. Recent residential and commercial development has brought new opportunities for growth while preserving the neighborhood’s historic charm. Highland Park’s walkable neighborhoods, strong local economy, and access to transportation, including Metra and major highways, make it an ideal location for those seeking convenience without compromising on community or character. Whether you're interested in the arts, nature, or simply a high quality of life, Highland Park has something for everyone.
1/23
Contingent

$1,225,210

3
Bedrooms
2,900
Square Feet
0.06
Acres

2528 Hidden Oak (lot 6) Circle, Highland Park, IL 60035

1/2
Contingent

$260,000

2
Bedrooms
1,296
Square Feet
0.16
Acres

1218 Taylor Avenue, Highland Park, IL 60035

1/32
Closed 4/24/25

$1,245,000

5
Bedrooms
3,741
Square Feet
0.4
Acres

1244 Sherwood Road, Highland Park, IL 60035

$1,196,975 | 1060 Livingston (lot 5) Avenue, Highland Park, IL 60035
1/16

$1,196,975

3
Bedrooms
2,600
Square Feet
0.06
Acres

1060 Livingston (lot 5) Avenue, Highland Park, IL 60035

a front view of house with yard and green space
1/2
Closed 5/7/25

$395,000

3
Bedrooms
1,120
Square Feet
0.21
Acres

860 Virginia Road, Highland Park, IL 60035

$4,550,000 | 2445 Woodbridge Lane, Highland Park, IL 60035
1/34
Listed By Compass

$4,550,000

6
Bedrooms
6,867
Square Feet
1.62
Acres

2445 Woodbridge Lane, Highland Park, IL 60035

a front view of house with yard outdoor seating and barbeque oven
1/25
Closed 4/1/25

$745,000

4
Bedrooms
1,886
Square Feet
0.32
Acres

2732 Summit Avenue, Highland Park, IL 60035

$340,000 | 415 Bloom Street, Highland Park, IL 60035
1/31
Closed 5/1/25

$340,000

3
Bedrooms
1,878
Square Feet
0.08
Acres

415 Bloom Street, Highland Park, IL 60035

a view of a house with fountain and porch
1/52
Listed By CompassVirtual Tour

$2,999,000

6
Bedrooms
7,640
Square Feet
1.07
Acres

493 Hazel Avenue, Highland Park, IL 60035

a front view of a house with a yard
1/61

$5,500,000

4
Bedrooms
4,600
Square Feet
4.10
Acres

147 Central Avenue, Highland Park, IL 60035

$950,000 | 1158 Glencoe Avenue, Highland Park, IL 60035
1/27
Listed By CompassPending

$950,000

4
Bedrooms
2,874
Square Feet
0.28
Acres

1158 Glencoe Avenue, Highland Park, IL 60035

a front view of a house with a garden
1/33

$999,000

5
Bedrooms
2,845
Square Feet
0.63
Acres

378 Oakland Drive, Highland Park, IL 60035

$569,000 | 1012 Windsor Road, Highland Park, IL 60035
1/14

$569,000

4
Bedrooms
2,895
Square Feet
0.20
Acres

1012 Windsor Road, Highland Park, IL 60035

$1,376,555 | 1064 Livingston (lot 3) Avenue, Highland Park, IL 60035
1/28

$1,376,555

5
Bedrooms
2,900
Square Feet
0.06
Acres

1064 Livingston (lot 3) Avenue, Highland Park, IL 60035

a front view of a house with yard
Closed 4/9/25

$625,000

3
Bedrooms
1,913
Square Feet
0.12
Acres

546 Broadview Avenue, Highland Park, IL 60035

$1,223,100 | 1062 Livingston (lot 4) Avenue, Highland Park, IL 60035
1/20

$1,223,100

4
Bedrooms
2,900
Square Feet
0.06
Acres

1062 Livingston (lot 4) Avenue, Highland Park, IL 60035

a front view of a house with a garden
1/10
Contingent

$799,000

4
Bedrooms
2,500
Square Feet
0.32
Acres

2542-2548 Green Bay Road, Highland Park, IL 60035

$1,261,830 | 1068 Livingston (lot 1) Avenue, Highland Park, IL 60035
1/11

$1,261,830

3
Bedrooms
2,250
Square Feet
0.06
Acres

1068 Livingston (lot 1) Avenue, Highland Park, IL 60035

a front view of a house with a garden
1/20
Contingent

$440,000

2
Bedrooms
1,285
Square Feet
0.26
Acres

107 Ridge Road, Highland Park, IL 60035

a front view of a house with a garden
1/30

$899,900

4
Bedrooms
3,472
Square Feet
0.3
Acres

545 Green Bay Road, Highland Park, IL 60035

$375,000 | 1244 Taylor Avenue, Highland Park, IL 60035
1/32
Closed 3/28/25

$375,000

3
Bedrooms
1,507
Square Feet
0.16
Acres

1244 Taylor Avenue, Highland Park, IL 60035

a front view of a house
1/13

$1,229,900

3
Bedrooms
2,250
Square Feet
0.06
Acres

1066 Livingston (lot 2) Avenue, Highland Park, IL 60035