New28$624,900
2 bd · 3 ba · 2,362 sqft
190 Leonard Wood S 106, Highland Park, IL
Stephanie Absler-Orsi · RE/MAX Top Performers
Homes for Sale in Highland Park, IL
Hide MapHomes for Sale in Highland Park, IL
24 of 54 Listings
New28$624,900
2 bd · 3 ba · 2,362 sqft
190 Leonard Wood S 106, Highland Park, IL
Stephanie Absler-Orsi · RE/MAX Top Performers
57$1,675,000
5 bd · 9 ba · 5,339 sqft
1745 Sundrop Circle, Highland Park, IL
Rita Masini · Compass
26$649,000
4 bd · 3 ba · 2,200 sqft
872 Virginia Road, Highland Park, IL
Annika Valdiserri · @properties Christie's International Real Estate
20$575,000
3 bd · 2 ba · 1,890 sqft
1767 Clifton Avenue, Highland Park, IL
Nancy Karp · @properties Christie's International Real Estate
36$2,500,000
5 bd · 4 ba · 5,443 sqft
89 Cary Avenue, Highland Park, IL
Ted Pickus · @properties Christie's International Real Estate
29$775,000
4 bd · 4 ba · 2,971 sqft
2843 Twin Oaks Drive, Highland Park, IL
Janet Borden · Compass
18$335,000
2 bd · 2 ba · 1,204 sqft
1250 Park Avenue 430, Highland Park, IL
Julie Carani Mangione · Coldwell Banker Realty
28$740,000
3 bd · 2 ba · 2,496 sqft
263 Barberry Road, Highland Park, IL
Joseph Ryan · Joseph D Ryan
48$2,200,000
4 bd · 4 ba · 4,322 sqft
165 Maple Avenue, Highland Park, IL
Janet Borden · Compass
30$625,000
3 bd · 2 ba · 1,708 sqft
475 Burton Avenue, Highland Park, IL
Cory Albiani · @properties Christie's International Real Estate
43$1,599,000
4 bd · 5 ba · 4,491 sqft
251 Oakland Drive, Highland Park, IL
Ted Pickus · @properties Christie's International Real Estate
40$1,350,000
4 bd · 4 ba · 2,300 sqft
1120 Ridgewood Drive, Highland Park, IL
Karen Skurie · Baird & Warner
33$525,000
4 bd · 2 ba · 1,279 sqft
1243 Ridge Road, Highland Park, IL
Lynn Fairfield · RE/MAX Suburban
36$679,000
4 bd · 3 ba · 2,647 sqft
815 Barberry Road, Highland Park, IL
Cheryl Waldstein · @properties Christie's International Real Estate
58$4,150,000
4 bd · 6 ba · 5,500 sqft
22 Lakeview Terrace, Highland Park, IL
Ted Pickus · @properties Christie's International Real Estate
45$1,699,000
5 bd · 4 ba · 3,884 sqft
1620 Ravine Terrace, Highland Park, IL
Cheryl Waldstein · @properties Christie's International Real Estate
35$1,045,000
5 bd · 4 ba · 4,092 sqft
1557 Cavell Avenue, Highland Park, IL
Nancy London · Baird & Warner
43$1,599,000
4 bd · 4 ba · 4,254 sqft
327 Marshman Avenue, Highland Park, IL
Cory Albiani · @properties Christie's International Real Estate
24$368,000
2 bd · 3 ba · 1,548 sqft
1071 Deerfield Place, Highland Park, IL
Stephanie Absler-Orsi · RE/MAX Top Performers
51$1,750,000
6 bd · 5 ba · 5,300 sqft
1848 Balsam Road, Highland Park, IL
Melissa Siegal · @properties Christie's International Real Estate
31$775,000
4 bd · 3 ba · 2,750 sqft
1752 McCraren Road, Highland Park, IL
Matt Laricy · Americorp, Ltd
58$3,450,000
5 bd · 7 ba · — sqft
Address withheld · Highland Park, IL
Joshua Lipton · Compass
59$1,599,000
6 bd · 7 ba · 5,000 sqft
215 Prospect Avenue, Highland Park, IL
Keith Goad · Berkshire Hathaway HomeServices Chicago
29$595,000
2 bd · 2 ba · 1,744 sqft
1353 Golf Avenue, Highland Park, IL
Susan Segal · @properties Christie's International Real Estate
Midwest Real Estate Data (MRED)Source: HJN community data
July 2026 · This period is still settling
Selling at 102.4% of asking price
Buyers here are paying above asking. MLS · 30 sales · as of Jul 20, 2026