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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 #11705842

86 Prospect Avenue, Highland Park, IL - $5,199,000

Residential, Detached Single
  • 8 Beds
  • 12 Baths
  • 17k SQFT
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Set On Nearly An Acre Of Lush Private Grounds Professionally-landscaped By Chicago's Famed Douglas Hoerr, On A Quiet Cul-de-sac Just Steps From The Shores Of Lake Michigan, Rests An Incomparable 17,000 Sq Ft Custom Gem. Unlike Any Offering On Chic...

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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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Beautifully Updated Home Situated In East Highland Park In The Ravinia District. This Custom Home 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-s...

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2448 Tennyson Lane, Highland Park, IL - $900,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 8,252 SQFT
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Located In Highland Park's Highridge Neigborhood, This Well Maintained, Landscaped, Brick 6 Bed/5.5 Bath Home Is A True Gem! A Dramatic Two-story Foyer Welcomes You Into The Home. Its Floor To Ceiling Windows Draws Your Eyes To The Serene And Priv...

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1365 Sheridan Road, Highland Park, IL - $1,529,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 4,792 SQFT
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This Is The Ideal East Highland Park Home To Make Your Own As It's All Here! Starting With A Lush Maturely Landscaped 1-acre Lot With Pool, Dual Pillar Entrance With An Elegant Stately Circular Driveway, Classic Red Brick Architecture, And An Incr...

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1910 Old Briar Road, Highland Park, IL - $1,475,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
  • 4,978 SQFT
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This Dramatic Home With A Large Circular Drive And Amazing Street Presence Sits On A Lush, Wide, Beautifully Landscaped Property. A Spacious Six-bedroom, Five Full, And One-half-bath Home With A Three-car Garage In A Desirable And Quiet Highland P...

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2545 Highmoor Road, Highland Park, IL - $875,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 4,449 SQFT
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Move Right Into This Immaculate And Well-appointed Cape Cod With An Expansive, Smooth-flowing Layout And Over 6,000 Square Feet Of Finished Living Space! Unique And Exciting Floor Plan Starting With A Large , Bright Foyer And Well-planned Living S...

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2090 Painters Lake Road, Highland Park, IL - $1,195,000

Residential, Detached Single
  • 2 Beds
  • 4 Baths
  • 2,770 SQFT
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Updated Spacious Grunsfeld Ranch In Desirable Painters Lake. This 3 Bedroom, 3 Full And 1 1/2 Bath Has Been Updated With So Many Improvements. Gorgeous Wide Plank Hardwood Floors In The Great Room And Entry, Newer Carpet In Bedrooms, Plus Finished...

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3090 Warbler Place, Highland Park, IL - $950,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,576 SQFT
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Spacious 6 Bedroom, 4 Full Bath & 1 Half Bath Home With 3 Car Garage In Desirable Highland Park Neighborhood. Dramatic Sun-drenched Foyer With Double Height Ceiling, Hardwood Floors, Sputnik Fixture & Double Entry Glass Doors. Large Formal Dining ...

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2021 Old Briar Road, Highland Park, IL - $1,649,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,400 SQFT
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Great Opportunity To Own This Modern Style Property To Be Occupancy Ready In The Fall Of 2023. Unique, Does Not Even Describe The Interior And Exterior Finishes. Windows, Interior And Exterior Doors, Tiles Imported From Europe. Open Floor Plan Wil...

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1920 Emerald Woods Lane, Highland Park, IL - $1,750,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 5,539 SQFT
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This Dramatic Custom Built Contemporary Home With A Circular Drive Sits On A Lush, Beautifully Landscaped Property, Close To An Acre. The Living Room And Foyer Feature Soaring, Wood Beamed Ceilings, Stunning Walls Of Windows, A Huge Gas Fireplace ...

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Photo of Listing #11682245

2124 Tennyson Lane, Highland Park, IL - $975,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 4,057 SQFT
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Serene, Sun-filled Contemporary Ranch On Private Wooded Acre Of Land Backing Up To The Conservancy In High Ridge. Over 7200 Useable Sq. Ft Including Basement. Beautiful Foyer Opens To The Great Room With Vaulted Ceilings And Floor To Ceiling Windo...

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23 Scott Loop, Highland Park, IL - $2,199,000

Residential, Detached Single
  • 7 Beds
  • 7 Baths
  • 6,168 SQFT
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Expanded, Remodeled And Recently Updated Fort Sheridan Captains Mansion Directly On Lake Michigan. Every Single Room In This House Has Unobstructed Views Of Lake Michigan!! High End Millwork And Finishes With Period Details Throughout, Solid Oak D...

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670 Crofton Avenue, Highland Park, IL - $1,350,000

Residential, Detached Single
  • 3 Beds
  • 3 Baths
  • 2,665 SQFT
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Another J & B Design North Shore Luxury Floor To Ceiling Renovation, Working In Tandem With Stuart Shayman & Associates Architects (renovation Starts December 2022 With Delivery In May 2023). This Time It's The Largest Home In The Prestigious Edge...

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1887 Cooper Lane, Highland Park, IL - $999,900

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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2040 Kipling Court, Highland Park, IL - $1,130,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 4,864 SQFT
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In-ground Pool And Tennis Court! Brand New Carpeting On Second Level Hallway! Enjoy Entertaining In Open Concept 6 Bedroom Home Nestled On Almost An Acre Of Land. Grand Double Doors Lead You Into Home's Voluminous Layout Offering Views Into Office...

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340 North Deere Park Drive W, Highland Park, IL - $1,500,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
  • 5,444 SQFT
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Incredible Opportunity To Live In Prime North Deere Park Location With Private Beach Access. This Classic Tudor Home Has Been Completely Updated For Today's Living. Features Include Crown Moldings, Hardwood Floors And Decorative Millwork. First Fl...

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Photo of Listing #11664488

2625 Mavor Lane, Highland Park, IL - $1,350,000

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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201 Moraine Road, Highland Park, IL - $3,950,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 6,300 SQFT
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Coming Soon From An Amazing Builder And Award Winning Architect- An Incredible Location Overlooking A Ravine, Near Lake Michigan And Downtown Highwood And Highland Park. Sophisticated Open Floor Plan With Full Length Windows Maximizes The Spectacu...

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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 January 27th, 2023 at 4:38pm CST.