Highland Park is an affluent North Shore community of homes 25 miles to downtown Chicago. As one of the larger communities, you will find many homes on stunning multiple acres with landscaped gardens and pools, offering riparian rights, private beaches, and views of Lake Michigan. The homes range from 1890 classics by Holabird & Root to modernist designs perched on bluffs by distinguished architect Tony Grunsfeld. LEARN MORE
| $750,000 - $1,000,000 | $1,000,000 - $2,000,000 | $2,000,000 - $3,000,000 |
| $3,000,000 - $5,000,000 | $5,000,000 - $10,000,000 |
Multiple Offers Received. Highest And Best Due 3/6 At 5pm. Situated On A Nearly Acre Parcel In A Sought-after North Shore Enclave, This Custom Ranch Offers Approximately 3,300 Square Feet Of Thoughtfully Designed Single-level Living. Seamless Ind...
Beautifully Maintained And Incredibly Spacious Colonial In Desirable Highland Park Offering 4 Bedrooms, 2.5 Baths, And A Fully Finished Basement. The Home Welcomes You With A Dramatic Two-story Foyer Featuring Hardwood Flooring And An Open Stairca...
Welcome To Your Dream House In Desirable Sherwood Forest With 2 Master Bedroom Suites! All Brand New And Giving You Peace Of Mind For Years To Come. This Stunning Spacious Contemporary Single-family House Has Been Tastefully And Completely Remodel...
Rare Opportunity In The Coveted Braeside School District, Ideally Situated On A Private Street And Set Along A Beautiful Ravine. Just Moments From Ravinia Festival, This Property Offers A Truly Special Location With Privacy, Natural Views, And Pro...
CONTINGENT This Classic Brick Tudor Seamlessly Blends Timeless Architectural Charm With Thoughtful Modern Updates. Set Along A Picturesque Ravine, The Home Features A Renovated Eat-in Kitchen, A Formal Dining Room Addition, And A Cozy First-floor Den/office ...
CONTINGENT This Exquisite Contemporary Ranch Sits On Close To 3 Acres And Feels Like A Wonderfully Luxurious Private Estate. The Amazing Floor Plan Is Filled With Natural Light, And Features 12 Foot Ceilings And A Spectacular Wall Of Windows Along The Back O...
Why Would You Want Ordinary When You Can Have Extraordinary! This Stunning And Majestic Brick Home Sits On Over An Acre In The Heart Of Highland Park And Features A 40' Indoor Pool With A Wall Of Glass That Opens To The Outdoors! Over 8000 Sq Ft P...
CONTINGENT Stunning, Extensively Renovated 5-bedroom, 4.1-bath Home In The Coveted Hybernia Community Of Highland Park, Offering Serene Pond Views And Maintenance-free Living. A Dramatic Two-story Foyer Welcomes You Into Light-filled Interiors Featuring Soa...
CONTINGENT Magnificent Charm And Character In This Updated Braeside Home. Gorgeous Re-modeled Kitchen With Custom Cabinets, Stainless Steel Professional Appliances, White Marble Counter Tops And Quaint Built In Seating Area. Year Round Sun Room That You Won'...
CONTINGENT Rarely Available 4,700 Sqft Ranch Set On An Expansive, Meticulously Landscaped Property Offering Exceptional Privacy And Presence. This Elegant 3 Bedroom, 4.1-bath Residence Is Thoughtfully Designed And Rich In Architectural Detail, Unfolding In A...
Located In The Coveted Belle Avenue Historic District, This Extraordinary Estate Sits On 2.3 Acres Of Manicured Grounds With Sweeping Lake Views. Fully Renovated And Expanded, The Residence Blends Timeless Elegance With Modern Luxury For A Truly O...
CONTINGENT 995 Harvard Ct Look No Further- 995 Harvard Court Is The Home You've Been Dreaming Of. Impeccably Maintained And Meticulously Updated, This 5 Bedroom 4 Full And 1 Half Bath Has Everything You Are Looking For In Desirable Sunset Park. A Charming...
Prime Highland Park Property Being Marketed As Complete Gut Rehab Or Tear Down On Private Cul De Sac With Higher Priced Homes. Option Is Yours To Remodel Or Tear Down And Build. Home And Property Are Being Sold In As Is Where Is Condition. Wood Bu...
CONTINGENT Set On Over An Acre In Highly Coveted High Ridge, This Exceptional Residence Is A Rare Blend Of Luxury, Scale, And Thoughtful Design. From The Moment You Arrive, The Home Makes A Statement - Elegant Yet Welcoming - Created For Those Who Value Both...
**a Rare Opportunity To Own This Magnificent, One-owner Stone And Brick Masterpiece. Nestled On A Spectacularly Landscaped 1.5 Acres With Breathtaking Views Of A Serene Prairie And A Private Walking Path Just Steps From Your Door, This Stunning Mo...
CONTINGENT Welcome To This Custom Contemporary Home, Beautifully Set On A Stunning .75-acre Lot With Ample Table Land And Breathtaking Ravine Views. Designed In 1979 By Renowned Architect Larry Booth, This Architectural Gem Seamlessly Blends Dramatic Design ...
CONTINGENT Move-in Ready 6-bedroom, 5 Full Bath And 1 Half-bath Brick Home Set On A Beautifully Landscaped Half-acre In A Sought-after Highland Park Neighborhood. Designed For Both Everyday Living And Entertaining, This Home Features An Open Floor Plan With ...
Among the lakefront communities on the North Shore, downtown Highland Park offers the most diverse shopping, dining, and personal care choices in a village setting. There are many professional services in the district and the Highland Park Hospital, the Library, the Art Center, and the North Shore Yacht Club are within walking distance. There are four Metra stations and the Pace bus system connects Highland Park to the network of trains in and around Chicago.
The Park District of Highland Park is home to 4 beaches, 34 parks, a racquet club, an ice arena, a golf course, water sports, a nature trail ideal for cross country skiing, and so much more.
District 112 serves Highland Park and parts of Highwood. It includes several elementary schools and two middle schools:
Township High School District 113: Township High School District 113 serves both Highland Park and neighboring Deerfield. It operates two high schools:
The North Shore Chicago listings on this page include Highland Park IL homes for sale. The property listings are updated as soon as they hit the market with new Highland Park homes for sale and rent. Start your home search and schedule showings online or to learn more about Highland Park and Chicago's North Shore call 312.961.6212
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 Sotheby's International Realty are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.
Listing information last updated on March 8th, 2026 at 12:53am CST.
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