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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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2700 Point Lane, Highland Park, IL - $14,855,000

Residential, Detached Single
  • 9 Beds
  • 19 Baths
  • 32.7k SQFT
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Nba Superstar Michael Jordan's Seven-acre Estate Is As Legendary As His Airness Himself. The 56,000 Square Foot Property-equipped With Every Conceivable Luxury Amenity-is A Physical Monument To His Tireless Dedication And Hard Work. The Custom Des...

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1869 Crescent Court, Highland Park, IL - $5,750,000

Residential, Detached Single
  • 7 Beds
  • 11 Baths
  • 9,647 SQFT
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This Trophy Property Offers An Ideal Sense Of Safety And Seclusion. A Rare Find In Chicago's North Shore, You Can Live On 2+ Beautifully Landscaped Acres Overlooking Lake Michigan. Tucked Away On A Quiet Cul-de-sac Block Directly East From Downtow...

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Photo of Listing #10642967

353 North Deere Park Drive E, Highland Park, IL - $5,150,000

Residential, Detached Single
  • 5 Beds
  • 9 Baths
  • 7,445 SQFT
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Situated On One Of The Most Desirable Locations On The North Shore, This Private Residence Was Built For Resort Style Living On A Rarely Found 1.5 Acre Lakefront Setting. Picturesque And Breathtaking, The Home Was Designed With Large Windows To En...

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Photo of Listing #10859523

41 South Deere Park Drive, Highland Park, IL - $4,900,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 7,436 SQFT
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Possessing The Most Breathtaking Sweeping Vistas Of Lake Michigan, Rarely Available In Any Lakefront Property, This Updated California Contemporary Lannon Stone Ranch-style Home With Vaulted Ceilings And Walls Of Windows Is Simply Spectacular. Off...

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Photo of Listing #10384989

959 Sheridan Road, Highland Park, IL - $4,875,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 7,800 SQFT
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Newer Construction On The Lake In East Highland Park. Enjoy The Sunrise Over The Lake And Unrestricted Water Views From All The Windows. 100 Feet Of Sandy Private Beach! Heated Indoor Pool. 6 Bedrooms, 6.2 Bath, Gourmet Kitchen With Oversized Isla...

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Photo of Listing #10804471

999 Sheridan Road, Highland Park, IL - $3,395,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 6,000 SQFT
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Now You Can Have It All!!! Lakefront Living With Private Sandy Beach. Utilize Stairs Or New Tram On The Property For Incredible Convenience And Luxury...walk Or Ride. Enjoy 180 Degree Breathtaking Views Of Lake Michigan All Year Long. A Rare Lakef...

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2625 Mavor Lane, Highland Park, IL - $3,300,000

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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Photo of Listing #10776689

297 North Deere Park Drive, Highland Park, IL - $2,994,000

Residential, Detached Single
  • 7 Beds
  • 7 Baths
  • 5,086 SQFT
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Old World Charm With A Contemporary Vibe, This Sun Filled Lakefront Home Has Been Meticulously Restored And Expanded. Remodeled By Van Burgen, Known For His Work With Stone, Studying And Working Under Frank Lloyd Wright. Two Story Open Foyer With ...

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3481 Bradley Court, Highland Park, IL - $2,950,000

Residential, Detached Single
  • 8 Beds
  • 7 Baths
  • 10.3k SQFT
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Seeing Is Believing! Enter This Large Gracious Custom-built Home To A Grand Statement Foyer, Spectacular Curved Staircase, Wrought-iron Railings, Custom Detailed Floors And Beautiful Arches, Moldings. Spacious First Floor Living Areas Are Elegant,...

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1511 Forest Avenue, Highland Park, IL - $2,500,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 5,178 SQFT
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Just 7 Yrs Old, This Unique Blend Of Warmth & Sophistication Offers The Latest Technology, Architectural Details, Quality Materials & Space. Enjoy 3 Levels Of Luxury + Spectacular Grounds & Views. The Flowing Open Floor Plan & Walls Of Windows Bri...

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3393 Old Mill Road, Highland Park, IL - $2,100,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
  • 9,568 SQFT
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Private Country Club Living,this Magnificent 6 Bed/5.1 Bath Home Sits On 2.6 Acres With Almost 10,000 Sq. Ft. Of Luxury Finished Living Space.the Grand Foyer With Valued Ceilings Leads You To The Two-story Living Room Flanked By A Wall Of Windows ...

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950 Sheridan Road, Highland Park, IL - $2,050,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 7,600 SQFT
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Stunning English Tudor Estate Situated On 2.3 Acres With Professional Landscaping And Lush Ravine Views! Perfectly Hidden From Sheridan Road. 5 Bedrooms/5.2 Baths. The First Floor Master Suite Has A Sizable Sitting Area Which Lets In The Morning L...

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1925 Emerald Woods Lane, Highland Park, IL - $2,000,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 6,083 SQFT
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The Privacy And Tranquility You Have Been Searching For. Upgraded Listing On An Expansive Rare 2-acre Property In Highland Park. This Luxurious Home Has An Open Floor Plan To Fit Your Family's Needs. Lushly Landscaped Grounds Designed By Award Wi...

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Photo of Listing #11008862

1700 Meadow Lane, Highland Park, IL - $1,999,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
  • 7,204 SQFT
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Rare Opportunity To Build Or Develop 8 Acres Property. One Of The Largest Contiguous Parcels Of Land In Highland Park, This Land Will Accommodate Multiple Houses Or A Family Compound. Beautifully Wooded Land With Open Meadows And Endless Possibili...

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228 Maple Avenue, Highland Park, IL - $1,899,900

Residential, Detached Single
  • 4 Beds
  • 7 Baths
  • 6,058 SQFT
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Luxury And Elegance In This Sun Filled Home On Half An Acre 2 Blocks Away From Downtown Highland Park And Lake Michigan. Fabulous Detail On This Open Floor Plan And Nicely Defined Rooms That Meet All Of Todays Buyers Needs. First Floor Handsome Of...

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1499 Sheridan Road, Highland Park, IL - $1,795,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
  • 6,167 SQFT
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Prime East Location For This Historical Victorian Home With An Ideal Floor Plan. Beautifully Expanded And Renovated, There Is Over 6000 Sf Possessing Architectural Characteristics Combining Original Character Together With Today's Modern Amenities...

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1793 Reserve Court, Highland Park, IL - $1,650,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 6,092 SQFT
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A Warm Welcome To A Stunning Custom Home Built In 2005. This Beautiful Piece Of Property, Located On A Cul-de-sac With Only 7 Neighbors, Provides Ultimate Privacy. Enter This Gracious Home Through A Two Story Foyer And That, Along With The Other...

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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

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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 March 4th, 2021 at 12:31pm CST.