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 |
Escape To Your Own Private Nature Retreat! Nestled On A Beautifully Large Wooded 1/3-acre Corner Lot In Coveted Sherwood Forest. This Exceptional 4092 Sq Ft Home Offers The Perfect Blend Of Space, Comfort, And Versatility To Fit Today's Lifestyle,...
Surrounded By The Peaceful, Natural Beauty Of The Hybernia Preserve, This Luxurious Home Offers Water Views And Privacy Seldom Experienced. ***new Roof, Gutters, And Patio - 2020***new Exterior Paint - 2023***kitchen Renovation - 2018***new Dishwa...
Situated On A Prestigious Private Lane In East Highland Park, This Rare Lakefront Offering Is A Mid-century Modern Masterpiece. Designed In 1957 By Renowned Architect Henry L. Newhouse Ii For Irving B. Harris, Chicago Philanthropist, This 10,000-s...
A Welcoming Front Porch Sets The Tone For The Warmth And Charm You'll Find Inside This Home. This Beautifully Maintained Brick Home Combines Timeless Character With Modern Updates, All Situated On An Expansive 50' X 220' Professionally Landscaped,...
This Exceptional Highland Park Residence Offers Nearly 5,300 Square Feet Of Impeccably Designed Living Space, Including A Beautifully Finished Lower Level, On An Expansive Lot Just Shy Of An Acre. Featuring 6 Bedrooms And 4.5 Baths Across Three Fi...
Nestled On A Private Property This Residence Stands As A Testament To Sophisticated Design And Timeless Elegance. This Custom-built Residence Is Poised On A Lush, Wooded Lot, Offering A Serene Backdrop That Feels Worlds Away While Remaining Moment...
CONTINGENT Enjoy Effortless Living In This Beautiful 4br/4.1ba Home Offering A Sought-after First-floor Primary Suite And Spectacular Ravine Views. Thoughtfully Designed With Spacious Living Areas And Abundant Natural Light, This Home Combines Timeless Elega...
CONTINGENT Set On A Beautifully Landscaped Property In Sought-after East Highland Park, This Luxurious Home Offers 5 Bedrooms And 5.1 Baths Across Thoughtfully Designed Living Spaces. Blending Classic Architectural Character With Modern Updates, The Home Is ...
A Rare Opportunity To Own This Beautifully Updated Contemporary Home With Over 5000 Sq Feet Of Living Space In One Of East Highland Park's Most Sought-after Neighborhoods. Featuring Two Large Primary Bedrooms With En-suite Bathrooms, One On The Ma...
CONTINGENT Nestled On A Picturesque Tree-lined Street In Sought-after East Highland Park, This Beautifully Updated 4-bedroom, 2.1-bath Home Seamlessly Blends Timeless Character With Today's Modern Conveniences. The Heart Of The Home Is A Stunning Chef's Kitc...
New Construction Luxury Single-family Home Coming Soon To Highland Park Within Sought After Ravinia Elementary School Boundaries. Designed For Both Everyday Living And Elevated Entertaining, The Main Level Features A Private Home Office With Strik...
Experience Unparalleled Luxury On The Lakefront. This 5,500 Sf New Construction Home Tucked Away At The End Of A Quiet Cul-de-sac Has Been Meticulously Curated For Modern Living With Impeccable Design. The Expansive Floor Plan Features Four Genero...
Welcome To Effortless Luxurious Living In Highland Park. This Stunning Custom Contemporary 6-year-young Home Offers 5 Spacious Bedrooms, 4 Half Baths, And An Open Floor Plan Bathed In Natural Sunlight From Every Angle. The Flexible Floor Plan Bl...
CONTINGENT Perfectly Nestled On A Serene Wooded Cul De Sac In West Highland Park, This Well Maintained Residence Sits On A .30 Acre Property With A Spacious Backyard. The Property Offers Over 3300 Sq Ft Of Flexible Living Space Featuring 4 Bedrooms And 3.5 B...
Nestled On A Quiet, Tree-lined Street In Highland Park's Coveted Braeside Neighborhood, This Spacious 4-bedroom, 3.1-bath Residence Presents A Rare Opportunity To Create Your Dream Home In One Of The North Shore's Most Desirable Communities. Fresh...
Tucked Away In One Of Highland Park's Most Coveted East-of-sheridan Enclaves, Just Moments From The Lakefront And Jaw-dropping Rosewood Beach, This Sprawling Residence Blends Timeless Architecture With Refined Amenities And Over 10,000 Square Feet...
CONTINGENT Nestled In The Highly Sought-after Braeside Neighborhood, This Sun-drenched 4-bedroom, 2.5-bath Split-level Home Offers The Perfect Combination Of Comfort, Style, And An Unbeatable Location. Just Steps From Ravinia Festival, The Vibrant Ravinia Bu...
CONTINGENT Welcome To This Beautifully Updated, Mid-century Ranch Home Situated On Just Under A Half-acre In The Highly Desirable Highlands Neighborhood Of Highland Park. Offering An Ideal Blend Of Spacious Living, Thoughtful Updates, And An Exceptional Loca...
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 July 21st, 2026 at 8:15pm CDT.
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