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Highland Park

Located on Lake Michigan, Highland Park is a picturesque suburb offering beautiful lake vistas, bluffs, ravines, and accessibility to Chicago. The vibrant downtown district is a pedestrian and cyclist-friendly outdoor shopping area filled with unique boutiques and delicious restaurants. Renowned for art and culture, Highland Park is home to many music festivals.

View The Market Report

Available Homes in Highland Park

2925 Parkside DR, Highland Park, IL 60035
Open Sun 1PM-3PM
36

$1,125,000

6 Beds 5.5 Baths 3,396 SqFt

2925 Parkside DR, Highland Park, IL 60035

Listed by Beth Wexler of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
2046 Saint Johns AVE #3E, Highland Park, IL 60035
Open Sat 12PM-1:30PM
33

$290,000

2 Beds 2 Baths 1,123 SqFt

2046 Saint Johns AVE #3E, Highland Park, IL 60035

Listed by Valentyna Artamonova of KOMAR

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
151 Maple AVE, Highland Park, IL 60035
Open Sun 1PM-3PM
46

$1,995,000

4 Beds 2.5 Baths 3,430 SqFt

151 Maple AVE, Highland Park, IL 60035

Listed by Tim Stassi of Dwell One Realty

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
1958 CASTLEWOOD RD, Highland Park, IL 60035
Open Sat 2PM-4PM
13

$550,000

3 Beds 2 Baths 1,616 SqFt

1958 CASTLEWOOD RD, Highland Park, IL 60035

Listed by Scott Rose of Baird & Warner

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
1795 Lake Cook RD #107, Highland Park, IL 60035
Open Sat 11AM-1PM
26

$349,000

2 Beds 2 Baths 1,418 SqFt

1795 Lake Cook RD #107, Highland Park, IL 60035

Listed by Michael Maggio of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
1223 Ridgewood DR, Highland Park, IL 60035
New
33

$675,000

3 Beds 2 Baths 1,750 SqFt

1223 Ridgewood DR, Highland Park, IL 60035

Listed by Earl Ruthman of Century 21 Circle

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
833 Laurel AVE #206, Highland Park, IL 60035
New
13

$3,860

2 Beds 2 Baths 1,396 SqFt

833 Laurel AVE #206, Highland Park, IL 60035

Listed by Shari Saratovsky of Diplomat Realty, Inc.

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
485 Ravine DR, Highland Park, IL 60035
New
40

$1,499,000

4 Beds 3.5 Baths 3,547 SqFt

485 Ravine DR, Highland Park, IL 60035

Listed by Debbie Scully of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
280 Aspen LN, Highland Park, IL 60035
New
39

$1,100,000

5 Beds 3.5 Baths 3,261 SqFt

280 Aspen LN, Highland Park, IL 60035

Listed by Beth Wexler of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
423 Pleasant AVE, Highland Park, IL 60035
New
37

$1,075,000

4 Beds 2.5 Baths 2,276 SqFt

423 Pleasant AVE, Highland Park, IL 60035

Listed by Joey Gault of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
830 Deerfield RD, Highland Park, IL 60035
New
40

$779,900

6 Beds 3 Baths 2,834 SqFt

830 Deerfield RD, Highland Park, IL 60035

Listed by Assya Zinger Vareljan of Berkshire Hathaway HomeServices Chicago

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
830 Deerfield RD, Highland Park, IL 60035
New
23

$5,800

6 Beds 3 Baths 2,834 SqFt

830 Deerfield RD, Highland Park, IL 60035

Listed by Assya Zinger Vareljan of Berkshire Hathaway HomeServices Chicago

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
2648 Western AVE, Highland Park, IL 60035
New
31

$550,000

5 Beds 3.5 Baths 2,340 SqFt

2648 Western AVE, Highland Park, IL 60035

Listed by Aaron Walsh of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
622 Pleasant AVE, Highland Park, IL 60035
New
14

$3,500

3 Beds 2 Baths 1,907 SqFt

622 Pleasant AVE, Highland Park, IL 60035

Listed by Patricia Denenberg of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
3290 Brook RD, Highland Park, IL 60035
New
40

$1,375,000

5 Beds 3.5 Baths 4,874 SqFt

3290 Brook RD, Highland Park, IL 60035

Listed by Pete Mangione of Coldwell Banker Realty

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
1284 Deerfield PL, Highland Park, IL 60035
Active Under Contract
34

$474,900

3 Beds 2 Baths 1,159 SqFt

1284 Deerfield PL, Highland Park, IL 60035

Listed by Peter Barber of Berkshire Hathaway HomeServices Chicago

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
1071 Deerfield PL, Highland Park, IL 60035
Active Under Contract
27

$375,000

2 Beds 2.5 Baths 1,548 SqFt

1071 Deerfield PL, Highland Park, IL 60035

Listed by Stephanie Absler-Orsi of RE/MAX Top Performers

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
215 Prospect AVE, Highland Park, IL 60035
Active
65

$1,690,000

6 Beds 6.5 Baths 5,000 SqFt

215 Prospect AVE, Highland Park, IL 60035

Listed by Keith Goad of Berkshire Hathaway HomeServices Chicago

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
559 Hillside DR, Highland Park, IL 60035
Active Under Contract
33

$925,000

5 Beds 3.5 Baths 4,426 SqFt

559 Hillside DR, Highland Park, IL 60035

Listed by Aaron Greenberg of Kale Realty

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
2130 Magnolia LN, Highland Park, IL 60035
Active
36

$1,199,999

5 Beds 3.5 Baths 3,256 SqFt

2130 Magnolia LN, Highland Park, IL 60035

Listed by Ted Pickus of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
370 Park AVE #E, Highland Park, IL 60035
Active
24

$3,250

2 Beds 2.5 Baths 2,000 SqFt

370 Park AVE #E, Highland Park, IL 60035

Listed by Emily Moore of Compass

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
427 Green Bay RD, Highland Park, IL 60035
Active Under Contract
50

$1,199,000

4 Beds 3.5 Baths 2,840 SqFt

427 Green Bay RD, Highland Park, IL 60035

Listed by Debbie Scully of @properties Christie's International Real Estate

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
50 Lakeside PL, Highland Park, IL 60035
Pending
9

$4,400

4 Beds 3 Baths 1,813 SqFt

50 Lakeside PL, Highland Park, IL 60035

Listed by Sonia Munwes Cohen of Coldwell Banker Realty

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
34 Logan LOOP, Highland Park, IL 60035
Active
72

$3,800,000

7 Beds 6.5 Baths 7,891 SqFt

34 Logan LOOP, Highland Park, IL 60035

Listed by Eileen Campbell of Jameson Sotheby's International Realty

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 06/13/2026. 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: 06/13/2026.

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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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