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Highland Park Homes for Sale and Rent

North Shore Chicago

Is it a buyer's or seller's market for Highland Park Homes? Learn more

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

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Homes for Sale in Highland Park

$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
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Photo of Listing #12363643

350 North Deere Park Drive W, Highland Park, IL - $1,600,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 3,117 SQFT
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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...

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Photo of Listing #12354274

419 Sheridan Road, Highland Park, IL - $825,000

Residential, Detached Single
  • 2 Beds
  • 2 Baths
  • 2,067 SQFT
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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...

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Photo of Listing #12370192

110 Lakewood Place, Highland Park, IL - $1,595,000

Residential, Detached Single
  • 6 Beds
  • 5 Baths
  • 4,972 SQFT
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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...

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Photo of Listing #12369642

1424 Glencoe Avenue, Highland Park, IL - $1,495,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 9,677 SQFT
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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...

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Photo of Listing #12369123

732 Bronson Lane, Highland Park, IL - $2,595,000

Residential, Detached Single
  • 6 Beds
  • 7 Baths
  • 9,659 SQFT
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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...

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Photo of Listing #12364321 CONTINGENT

2018 Linden Avenue, Highland Park, IL - $899,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,222 SQFT
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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 ...

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Photo of Listing #12364712 CONTINGENT

265 Ivy Lane, Highland Park, IL - $1,300,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,300 SQFT
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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...

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441 Oakland Drive, Highland Park, IL - $1,150,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,335 SQFT
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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...

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Photo of Listing #12359547 CONTINGENT

780 Highland Place, Highland Park, IL - $1,145,000

Residential, Detached Single
  • 5 Beds
  • 4 Baths
  • 4,201 SQFT
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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...

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Photo of Listing #12363028 CONTINGENT

186 South Deere Park Drive, Highland Park, IL - $990,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,976 SQFT
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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...

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Photo of Listing #12346514 CONTINGENT

1784 Reserve Court, Highland Park, IL - $1,649,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 4,690 SQFT
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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 ...

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1630 Ridge Road, Highland Park, IL - $4,750,000

Residential, Detached Single
  • 6 Beds
  • 9 Baths
  • 9,625 SQFT
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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...

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1857 Cloverdale Avenue, Highland Park, IL - $949,000

Residential, Detached Single
  • 4 Beds
  • 3 Baths
  • 3,108 SQFT
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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,...

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49 Red Oak Lane, Highland Park, IL - $995,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,478 SQFT
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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...

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Photo of Listing #12325689 CONTINGENT

1621 Grove Avenue, Highland Park, IL - $875,000

Residential, Detached Single
  • 6 Beds
  • 5 Baths
  • 3,354 SQFT
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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...

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Photo of Listing #12330124 CONTINGENT

215 Prospect Avenue, Highland Park, IL - $1,875,000

Residential, Detached Single
  • 6 Beds
  • 7 Baths
  • 5,000 SQFT
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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...

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314 Whistler Road, Highland Park, IL - $1,049,000

Residential, Detached Single
  • 3 Beds
  • 4 Baths
  • 3,141 SQFT
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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...

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Photo of Listing #12351749 CONTINGENT

1939 York Lane, Highland Park, IL - $1,079,000

Residential, Detached Single
  • 3 Beds
  • 3 Baths
  • 2,804 SQFT
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***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 ...

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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. 

 Here are the main school districts in Highland Park:

District 112 serves Highland Park and parts of Highwood. It includes several elementary schools and two middle schools:

  1. Township High School District 113: Township High School District 113 serves both Highland Park and neighboring Deerfield. It operates two high schools:

    •  Highland Park High School offers a comprehensive educational program for students in grades 9-12. It provides a wide range of academic courses, extracurricular activities, and sports teams.
    • Deerfield High School: Deerfield High School is located in Deerfield, but it serves a portion of Highland Park. It also offers a strong academic program and various extracurricular opportunities.

 Private schools near Highland Park:

Browse Highland Park Homes to Rent

Explore North Shore Homes by Community

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

 

 

 

Midwest Real Estate Data LLC Logo 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.