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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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Explore 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 Over $10,000,000
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Photo of Listing #11632133

611 County Line Road, Highland Park, IL - $1,499,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 4,713 SQFT
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Showings Start September 30th. Absolutely Stunning, Timeless, Brick Colonial With A Slate Roof, Beautifully Renovated, And Expanded With All High-end Designer Finishes. This Home Delivers The Best Of Both Worlds, Seamlessly Blending Old World Char...

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1533 Sheridan Road, Highland Park, IL - $1,500,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 4,361 SQFT
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Very Unique Opportunity...boasting An Array Of Sleek Finishes And A Thoughtful Open Plan Layout, This Ground-up New Construction Modern Farmhouse On Sheridan Road In Highland Park Is In An Unbelievable Location....2 Blocks Away From The Metra, 4 B...

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1098 Ridgewood Drive, Highland Park, IL - $1,300,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 6,509 SQFT
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Vintage Charm Meets Modern Amenities! This Fabulous Center-entry 3-story Colonial On More Than 3/4 Of An Acre Will Surprise You With Tasteful Renovations And An Impressive Expansion. Over 6500 Square Feet Above Grade Including 5 Bedrooms, 5 Full...

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1649 Ravine Terrace, Highland Park, IL - $1,350,000

Residential, Detached Single
  • 7 Beds
  • 6 Baths
  • 7,643 SQFT
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Never Before On The Market! Presenting 1649 Ravine Terrace, Masterfully Designed By The Late Ernest Grunsfeld. This East Highland Park Gem Offers Serenity, Privacy And Endless Opportunity Sitting On An Expansive 1.5 Acres And Perfectly Situated At...

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2510 Highmoor Road, Highland Park, IL - $1,149,000

Residential, Detached Single
  • 6 Beds
  • 7 Baths
  • 5,900 SQFT
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New England Wide Shingle Style Large Home Situated On Almost An Acre Of Land Has Everything From Your Wish List. Extensively Updated And Renovated. Custom-built With Copper, Cedar Shake & Hardwoods Inside And Out, Two Stairways, Enclosed Veranda, ...

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37 Sheridan Road, Highland Park, IL - $2,700,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
  • 7,106 SQFT
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Perfection! Complete Renovation Of This Stunning 6 Bedroom /6.5 Bath Home Situated On Nearly An Acre Of Lushly Landscaped Property With Beautiful Ravine Views And Privacy. Nate Berkus Associates Did Not Miss One Detail When Designing The Finishes ...

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2320 Shady Lane, Highland Park, IL - $1,749,000

Residential, Detached Single
  • 7 Beds
  • 8 Baths
  • 8,228 SQFT
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New Major Improvements To Enormous Home With 13,000 Feet Of Living Space On Over 2-acre Oasis. Owner Will Consider Below-market Financing If Under Contract By October 15, 2022. Rebuilt Huge Deck And Resurfaced Pool Among Recent Owner Investments. ...

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2036 Malory Lane, Highland Park, IL - $1,250,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,588 SQFT
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This Picturesque 5 Bedroom And 3.5 Bathrooms Home On 1 Acre Re-done From Top To Bottom! 5 Car Garage, Circular Brick Paver Driveway! Grand Portico Front With Fountain! Full Finished Basement With Home Theater, Bar And Extra Bedroom. Enjoy Your Per...

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757 Baldwin Road, Highland Park, IL - $2,195,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 5,838 SQFT
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Privately Situated, This Ravinia Masterpiece Created By Orren Pickell Sits On An Oversized Lot That Is On One Of The Loveliest Streets In Highland Park. From The Moment You Enter The Soaring 2-story Foyer With Spectacular, Yet Gracious, Staircase,...

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1230 Linden Avenue, Highland Park, IL - $1,469,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,440 SQFT
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A Classic Mid Century Modern Home Reimagined For Today's Lifestyle. Sometimes, You Can Judge A Book By Its Cover! This House, With Its Clean Architectural Lines, Inviting Blend Of Colors And Textures, Gives A New Meaning To Welcome Home. Rebuilt F...

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1910 Old Briar Road, Highland Park, IL - $1,500,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
  • 4,978 SQFT
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Beautifully Situated On An Exceptional Half-acre Landscaped Lot, This Stunning And Dramatic Residence With Amazing Street Presence And Large Circular Driveway Screams Welcome Home. This Pristine One-owner Six Bedroom, Five Full And One Half Bath ...

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Photo of Listing #11613165

54 Laurel Avenue, Highland Park, IL - $2,700,000

Residential, Detached Single
  • 8 Beds
  • 8 Baths
  • 6,927 SQFT
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Incredibly Rare Opportunity To Own A Lakefront Historic Landmark Home! Sitting Majestically On Approximately 2/3 Of An Acre This Home Is Surrounded By More Than 2 Acres Of Protected Land Including Ravine And Bluff That Is Owned/maintained By The ...

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1887 Cooper Lane, Highland Park, IL - $1,100,000

Residential, Detached Single
  • 4 Beds
  • 8 Baths
  • 5,625 SQFT
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Absolutely Stunning Custom 2004 Built, All Brick 8000+ Square Foot Home On 3 Levels Offering Of Luxury. 6 Bedrooms With 6 Full And 2 Half Bathrooms. Stunning Front Entrance And Foyer Welcomes You To Custom Tile Art Work And Millwork. Sun-drenche...

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Photo of Listing #11616506

2625 Mavor Lane, Highland Park, IL - $1,950,000

Residential, Detached Single
  • 6 Beds
  • 9 Baths
  • 13k SQFT
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Brand-new Unique And Modern Construction On 1.76 Acres W/ Over 13,000 S.f. Of Living Space. This House Will Meet All Your Needs With Customizable Living Space With Abundant Natural Light. Impressive Foyer Highlights The Impressive Building With A...

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791 Thackeray Drive, Highland Park, IL - $995,000

Residential, Detached Single
  • 6 Beds
  • 7 Baths
  • 5,482 SQFT
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Grand And Stately Are The Best Words To Describe This 5,500 Square Foot Home On Over A Half Acre Lot. From The Moment You Walk In The Luxurious Marble Floor Foyer You Feel The Grandeur Of The Home, With Large Living Room And Dining Room Flanking ...

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1750 Sundrop Circle, Highland Park, IL - $975,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 4,560 SQFT
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Wonderful Home, Impeccably Cared-for By The Original Owner In One Of The Best Locations Within Hybernia. Breathtaking Views Of Open Lands And Ponds! Beautifully Constructed With Vaulted Ceilings, Huge Updated Kitchen With Subzero Fridge, Wolf Doub...

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334 Lakeside Place, Highland Park, IL - $949,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 2,724 SQFT
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Explore The Click-by-click Virtual Tour! Stunning 4 + 1 Bedroom, 4.5 Bathroom Paradise In Prime East Braeside Neighborhood, Located On The Ravine At The End Of A Quiet Street! Impeccably Landscaped With Numerous Boxwoods, Gorgeous Flowering Bush...

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Photo of Listing #11489268

840 Croftridge Lane, Highland Park, IL - $1,059,000

Residential, Detached Single
  • 3 Beds
  • 4 Baths
  • 3,490 SQFT
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840 Croftridge Lane Is Located Near Town On A Private, Street With Maintenance Free Amenities. Located On A Premium Lot, The Home Has Ample Yard Space And Backs Up To A Pretty Wooded Area. The Home Features A First Floor Primary Suite. It Lives ...

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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.

Highland Park is renowned for its excellent schools including North Shore School District 112 featuring one PreK, eight elementary schools,and three middle schools. LEARN MORE

Highland Park High School, rated above the state average in key measures of college and career readiness, is in Township High School District 113 LEARN MORE

There are 22 private schools within five miles of Highland Park LEARN MORE

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. LEARN MORE

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

Browse Highland Park Homes to Rent

 

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 October 1st, 2022 at 6:38pm CDT.