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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

1099 Princeton AVE, Highland Park, IL 60035
Open 6/21 10AM-12PM
17

$415,000

2 Beds 1 Baths 1,050 SqFt

1099 Princeton AVE, Highland Park, IL 60035

Listed by Jennifer Boudreau of Compass

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
327 Marshman ST, Highland Park, IL 60035
Open Sun 2PM-4PM
50

$2,080,000

4 Beds 3.5 Baths 4,254 SqFt

327 Marshman ST, Highland Park, IL 60035

Listed by Jonathan Minerick of Homecoin.com

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
1804 Winthrop RD, Highland Park, IL 60035
Open 6/21 10AM-12PM
20

$539,999

3 Beds 2 Baths 1,534 SqFt

1804 Winthrop RD, Highland Park, IL 60035

Listed by Jennifer Boudreau of Compass

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
1958 CASTLEWOOD RD, Highland Park, IL 60035
Open Sun 1PM-3PM
15

$499,000

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
50 Lakeside PL, Highland Park, IL 60035
Open Sun 2PM-4PM
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
282 Linden Park PL, Highland Park, IL 60035
Open Sun 11AM-2PM
40

$3,199,999

6 Beds 6 Baths 6,325 SqFt

282 Linden Park PL, Highland Park, IL 60035

Listed by Linda Levin of Jameson Sotheby's Intl Realty

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
980 Half Day RD, Highland Park, IL 60035
New
37

$875,000

4 Beds 3.5 Baths 3,000 SqFt

980 Half Day RD, Highland Park, IL 60035

Listed by Alan Berlow of Coldwell Banker Realty

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
319 Hastings AVE, Highland Park, IL 60035
New
23

$849,000

4 Beds 2.5 Baths 2,328 SqFt

319 Hastings AVE, Highland Park, IL 60035

Listed by Beth Alberts of Compass

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
3107 Dato AVE, Highland Park, IL 60035
New
32

$699,000

3 Beds 2.5 Baths 1,877 SqFt

3107 Dato AVE, Highland Park, IL 60035

Listed by Valentyna Artamonova of KOMAR

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
3107 Dato AVE, Highland Park, IL 60035
New
53

$4,500

3 Beds 2.5 Baths 1,877 SqFt

3107 Dato AVE, Highland Park, IL 60035

Listed by Valentyna Artamonova of KOMAR

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
3203 Dato AVE, Highland Park, IL 60035
New
25

$719,000

3 Beds 3 Baths 2,163 SqFt

3203 Dato AVE, Highland Park, IL 60035

Listed by Susan Hayes of Baird & Warner

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
458 Naida TER, Highland Park, IL 60035
New
35

$1,299,000

5 Beds 4.5 Baths 3,284 SqFt

458 Naida TER, 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
639 Melody LN, Highland Park, IL 60035
New
13

$699,000

4 Beds 2 Baths 1,368 SqFt

639 Melody LN, Highland Park, IL 60035

Listed by Debra Baker of Compass

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
1494 Oakwood AVE, Highland Park, IL 60035
New
35

$799,000

4 Beds 3 Baths 2,228 SqFt

1494 Oakwood AVE, Highland Park, IL 60035

Listed by Janet Borden of Compass

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
2214 Churchill LN, Highland Park, IL 60035
New
69

$3,850,000

6 Beds 9 Baths 10,000 SqFt

2214 Churchill 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
552 Burton AVE, Highland Park, IL 60035
New
23

$615,000

4 Beds 2 Baths 1,818 SqFt

552 Burton AVE, Highland Park, IL 60035

Listed by Jeanine Shimer of Baird & Warner

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
639 Melody LN, Highland Park, IL 60035
New
13

$4,200

4 Beds 2 Baths 1,368 SqFt

639 Melody LN, Highland Park, IL 60035

Listed by Debra Baker of Compass

Midwest Real Estate Data (MRED) IDX
Midwest Real Estate Data (MRED) IDX
485 Ravine DR, Highland Park, IL 60035
Active Under Contract
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
2925 Parkside DR, Highland Park, IL 60035
Active
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
280 Aspen LN, Highland Park, IL 60035
Active
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
Active Under Contract
37

$1,075,000

4 Beds 2.5 Baths 2,276 SqFt

423 Pleasant AVE, 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
830 Deerfield RD, Highland Park, IL 60035
Active
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
2046 Saint Johns AVE #3E, Highland Park, IL 60035
Price Dropped by $5K
33

$285,000

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
2648 Western AVE, Highland Park, IL 60035
Active
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

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 06/21/2026. 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: 06/21/2026.

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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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