New32$1,195,000
3 bd · 3 ba · 2,951 sqft
723 Detamble Avenue, Highland Park, IL
Meredith Pierson · Compass
Luxury Homes in Highland Park, IL
Hide MapLuxury Homes in Highland Park, IL
24 of 27 Listings
New32$1,195,000
3 bd · 3 ba · 2,951 sqft
723 Detamble Avenue, Highland Park, IL
Meredith Pierson · Compass
58$3,900,000
4 bd · 6 ba · 5,500 sqft
22 Lakeview Terrace, Highland Park, IL
Ted Pickus · @properties Christie's International Real Estate
57$1,675,000
5 bd · 9 ba · 5,339 sqft
1745 Sundrop Circle, Highland Park, IL
Rita Masini · Compass
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
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
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
Price Reduced43$1,499,000
4 bd · 4 ba · 4,254 sqft
327 Marshman Avenue, Highland Park, IL
Cory Albiani · @properties Christie's International Real Estate
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
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
76$1,995,000
6 bd · 8 ba · 10,795 sqft
260 Beech Street, Highland Park, IL
Karen Biazar · North Clybourn Group, Inc.
27$1,395,000
2 bd · 4 ba · 2,330 sqft
23 Heritage Drive, Highland Park, IL
Marla Fox · Compass
32$1,249,000
3 bd · 3 ba · 2,951 sqft
723 Detamble Avenue, Highland Park, IL
Meredith Pierson · Compass
27$2,500,000
5 bd · 7 ba · 5,072 sqft
701 Lincoln Avenue W, Highland Park, IL
Beth Wexler · @properties Christie's International Real Estate
35$4,995,000
9 bd · 14 ba · 10,777 sqft
2441 Woodbridge Lane, Highland Park, IL
Rebecca Gilberg · Compass
Price Reduced29$1,150,000
5 bd · 6 ba · 6,360 sqft
201 Aspen Lane, Highland Park, IL
Gloria Matlin · Compass
16$4,399,000
5 bd · 6 ba · — sqft
966 Wade Street, Highland Park, IL
William Goldberg · Fulton Grace Realty
33$1,399,000
4 bd · 5 ba · 3,400 sqft
2009 Skyelar Court, Highland Park, IL
Janis Kirshner · Engel & Voelkers Chicago North Shore
52$2,599,000
6 bd · 7 ba · 8,256 sqft
493 Hazel Avenue, Highland Park, IL
Janet Borden · Compass
36$1,095,000
5 bd · 6 ba · 3,396 sqft
2925 Parkside Drive, Highland Park, IL
Beth Wexler · @properties Christie's International Real Estate
69$3,800,000
7 bd · 7 ba · 7,891 sqft
34 Logan Loop, Highland Park, IL
Eileen Campbell · Jameson Sotheby's International Realty
Price Reduced56$4,399,900
4 bd · 8 ba · 9,437 sqft
2665 Bentley Road, Highland Park, IL
Beth Wexler · @properties Christie's International Real Estate
Price Reduced62$1,495,000
5 bd · 6 ba · 5,819 sqft
3464 Old Mill Road, Highland Park, IL
Kelly Ipjian · Exit Strategy Realty
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