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 |
Gracious Braeside Tudor In Southeast Highland Park. This Classic Home Has Private Beach Rights And Overlooks The Lush Ravine. The Home Has Been Completely Renovated By Current Owners, Combining Traditional Charm With 21st Century Upgrades. Prof...
Welcome To This East Highland Park Ranch Home That Is Located On A Corner Lot And Only Steps From Ravinia Festival In Braeside. This Two Bedroom Spacious One Level Home Is Much Larger Than It Sounds With A Vaulted Great Room Addition. There Is A S...
Repositioned For Immediate Sale. Exceptional Value For Ravinia Living With Nearly 5,000 Sq Ft Above Grade And Private Lake Michigan Beach Access Just Seven Houses Away. Seller Will Contribute $10,000 Toward Buyer's Interest Rate Buydown Or Closing...
A Timeless Masterpiece In East Highland Park, Nestled On One Of The Area's Most Coveted Double Lots, This Opulent Residence Combines Exceptional Luxury With Modern Sophistication For Today's Most Desired Lifestyle. Impeccable Design + Details Comb...
A Nagle Hartray-designed Architectural Showstopper, This Unique And Meticulously Upgraded Residence Sits On A Lushly Landscaped Acre Near Rosewood Beach And Ravinia. Newly Enhanced With Bespoke Updates That Blend Timeless Design With Modern Refine...
CONTINGENT If You're Looking For A Home In A Fabulous Walk To Town Location With Shopping, Restaurants, The Metra And The Lake And Beach Right At Your Door, Then This Is The House For You! This Home Combines Charm With Many Modern Updates And Is Perfect For ...
CONTINGENT This Beautifully Renovated 5 Bedroom, 4 Full And 1 Half Bath Colonial Home Blends Timeless Elegance With Modern Luxury In Desirable Braeside Location. This Home Features High-end Finishes And Hardwood Floors Throughout. The Main Level Offers An Id...
Braeside Beauty On Established Tree Lined Street. Listen To Music From Ravinia On Your Charming Front Porch. If You Think The Outside Is Charming Wait Until You See The Inside! Large Kitchen With Island And Breakfast Bay Area. Kitchen Opens To Spa...
CONTINGENT This Spacious 2-story Home With A Great Mid Century Vibe, Is In A Highly Desirable Ravinia Neighborhood With Sidewalks, Wide Streets And A Short Walk To Ravinia, Chicago Botanic Gardens, Wonderful Shops And Restaurants And The Metra Train! This Gr...
CONTINGENT Explore The Property Through An Immersive Virtual 3d Tour And Discover A Truly Unique Home. Nestled At 186 South Deer Park Drive, In Highland Park, Just Steps From Glencoe And Lake Michigan, This Exquisite 4-bedroom, 3 Full Bath, And 2 Half Bath R...
CONTINGENT Stunning Award-winning Orren Pickell Home On Nearly One Acre Features Luxury Living Throughout. The Exceptional 5-bedroom, 5.5-bathroom Custom Estate Has Oversized Rooms, Rich Architectural Details, 3 Indoor Fireplaces And Seamless Indoor-outdoor ...
First Time On The Market With Only One Owner Having Lived Here, You'll Find A 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 Entertai...
Thoughtfully Updated Bright Four Bedroom Colonial In Sherwood Forest Ready For You Now. The Kitchen And All Baths Including The Powder Room Are Tastefully Renovated To The Highest Of Standards. The Kitchen Remodel Is Complete With Omega Cabinetry,...
Beautiful Red Brick Colonial Is A Family's Dream! Located On An Expansive Lot With A New Roof, Gutters And Downspouts, Light Oak Hardwood Floors And Floor-to-ceiling Windows That Flood The Home With Natural Light. The Backyard Feels Like A Private...
CONTINGENT A Home With Heart...this Beautifully Custom-built Home, Designed By The Seller In 2001, Was Thoughtfully Crafted For Comfort And Functionality-perfect For Any Household. The Heartbeat Of The Home Is A Stunning Kitchen, Featuring Rich Cabinetry, Sl...
CONTINGENT Stunning Howard Van Doren Shaw English Arts And Crafts Home On Over An Acre Of Magnificently Landscaped Property, One And A Half Blocks From Lake Michigan. Fine Architectural Detailing Throughout, Including The 2017 Renovated Kitchen Completed Wit...
Nestled On A Picturesque Meadow With Serene Pond Views, This Stunning 3-bedroom, 3.5-bath Home Offers Over 4,800 Sq. Ft. Of Total Living Space. Designed For Both Elegance And Comfort, The Main Level Spans 3,141 Sq. Ft. With Soaring 10-ft. Ceilings...
CONTINGENT ***multiple Offers Received. Best & Final Offers Due By Monday, 5/5 At 1pm. No Escalation Clauses! Fall In Love With This Fabulously Updated 3 Bed, 2.5 Bath Mid-century Modern Ranch Home With An Attached 2 Car Garage With Individual Driveways And ...
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 May 22nd, 2025 at 4:08am CDT.
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