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 |
CONTINGENT This Expansive Brick Ranch On A Half-acre Wooded Lot In The Sought After Sherwood Forest Neighborhood Was Extensively Remodeled And Designed By Ilene Chase Design. Brand New Flooring, Kitchen, And Baths To The Roof, Chimney, Landscaping, And Drive...
This Spacious (over 4200 Sq Ft Above Grade), Dramatic, Mid-century Contemporary Home Was Originally The Developer's Personal Home And Is One Of The Largest In The Area. Features Include A Circular Driveway, Large Wooded Lot, 2 Fireplaces, Two Stor...
CONTINGENT Move Right Into This Updated Braeside Beauty And Instantly Improve Your Lifestyle! A Recent Kitchen Renovation With White Wood Cabinetry And A Circular Floor Plan Are The Main Attraction. Well-scaled Rooms Throughout With Good Space For Everyone. ...
Thornycote A 1901 English Arts And Crafts Design By Howard Van Doren Shaw, Is A Home Where Craftsmanship, Harmony, And Grace Still Define Daily Life. Set On Over An Acre Of Lush, Landscaped Land Near Lake Michigan, This Residence Invites Admiratio...
CONTINGENT Fabulous Ranch In Maintenance-free Hybernia Offers Effortless Single-level Living With Upscale Finishes Throughout. The Inviting Great Room Features Vaulted Ceilings And A Newly Designed Stone Fireplace Flanked By Custom Cabinetry. Floor-to-ceili...
Magnificent Stone And Brick Masterpiece That Rests On Just Under A Spectacularly Landscaped 1.5 Acres. This Elegant Home Lives Like A Ranch And Was Designed For Entertaining From The Inside Out. First Floor Master Suite Complete With Sitting Room,...
CONTINGENT Set On A Beautifully Landscaped Half-acre Lot With A Circular Drive, 2276 Linden Is A Stunning Georgian Residence That Blends Classic Character With Thoughtful Updates And Modern Luxury. With Exceptional Curb Appeal, This Meticulously Maintained H...
CONTINGENT Unique One Of A Kind Log Cabin Home On .63 Of Wooded Acre With Ravine. 5 Bedrooms, 3 Full Baths, Basement And 3 Car Heated Garage. Beamed Vaulted Ceiling Family Room With Fireplace, Fireplace In Primary Suite As Well. 2 Bedrooms Have Separate Wing...
Welcome To 1839 Shelley Court - An Ultra-luxury, New-construction North Shore Home Situated On Nearly An Acre Lot And Tucked Back On A Private Cul-de-sac In The Coveted High Ridge Neighborhood. This Remarkable Residence Offers 6,600 Square Feet Of...
Historic Queen Anne Mansion Overlooking Lake Michigan! Set On A Private 3/4 Acre. Very Private, Only One Neighbor-surrounded On Three Sides By Park,ravine, And Lake, Adding "borrowed Landscape". Nuhaus Kitchen Overlooks Lake. Gorgeous Views Everyw...
Move Right In To This Immaculate 5 Bedroom, 4.5-bath New Construction Home That Blends Luxury, Comfort, And Functionality. Designed With A Seamless Open Floor Plan, This Home Is Perfect For Entertaining And Everyday Living. The Chef's Kitchen Feat...
CONTINGENT This Beautiful Home Is Just Steps Away From A Tranquil Oasis W/ Nature And Walking Paths For Miles. Luxury Finishes Throughout The Home! Designed With Custom Cabinetry, Quartz Counter Tops Throughout, Fireplace, Solid Core 8' Doors, Designer Light...
CONTINGENT Impeccably Renovated And Thoughtfully Upgraded, This 4,225 Sq. Ft., 4-bedroom, 5-bathroom Home In Northern Highland Park Perfectly Blends Modern Luxury With Timeless Design. Taken Down To The Studs During A Complete 2019-2020 Renovation, The Home ...
CONTINGENT Welcome To Legacy Club - Highland Park's Premier Maintenance-free Community. Built In 2001, This Impeccably Maintained Brick Home Delivers 3,684 Sq. Ft. Of Thoughtfully Designed Living Space. There Is A Bright, Open Floor Plan, Including Family R...
Completely Transformed With Top-to-bottom Renovations And Designer Upgrades, This Home Feels Brand New. The Impressive Foyer With Its Stunning Staircase Is Flanked By A Formal Living Room And Dining Room, Setting The Tone For The Thoughtful Design...
Last New Ranch Home Left In The Subdivision! Construction Is Already Underway On This Spectacular, Brand New Ranch Home In An Established, Maintenance-free Subdivision In The Perfect Highland Park Location And Cul-de-sac, As Part Of The Serenity ...
CONTINGENT Step Into History Reimagined. This Beautifully Renovated And Expanded Residence In The Heart Of The Historic Fort Sheridan Subdivision Seamlessly Blends Timeless Charm With Modern Amenities. Once A Duplex Home For Lieutenant Colonels, This Distin...
Welcome To 55 Prospect Avenue-where Every Day Feels Like A Seaside Escape. Perfectly Sited On 1.5 Acres With An Extraordinary 175 Feet Of Private Lake Michigan Beachfront, This Coastal-inspired Estate Offers A Rare Blend Of Architectural Elegance,...
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 December 16th, 2025 at 8:53pm CST.
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