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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

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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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41 South Deere Park Drive, Highland Park, IL - $5,500,000

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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353 North Deere Park Drive E, Highland Park, IL - $5,350,000

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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959 Sheridan Road, Highland Park, IL - $4,975,000

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 #10556952

6 Cliff Road, Highland Park, IL - $3,990,000

Residential, Detached Single
  • 4 Beds
  • 8 Baths
  • 5,800 SQFT
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First Time On The Market Ever! Literally Step Out Of Your Yard And Onto The Beaches Of The Shore Of Lake Michigan. Designed By Legendary Architects Holobird & Root And Built In 1890, The Former Fort Sheridan Pumping Station Was Transformed To Resi...

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289 Prospect Avenue, Highland Park, IL - $3,750,000

Residential, Detached Single
  • 6 Beds
  • 8 Baths
  • 7,591 SQFT
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This 2005 Built House Has It All! In Ground Pool, Indoor Basket Ball Court, Exercise Room, Movie Theater Room, 1st Floor Over Sized Office, 5 Bedrooms On 2nd Floor, En-suite Bedrooms On 1st Floor And In Basement. A Total Of 7 Bedrooms, 7 Full Bat...

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999 Sheridan Road, Highland Park, IL - $3,595,000

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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143 Cary Avenue, Highland Park, IL - $3,490,000

Residential, Detached Single
  • 5 Beds
  • 9 Baths
  • 9,492 SQFT
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Timeless. Gracious. Private. A Stately, French Normandy-style Home In Sought After East Highland Park? Say No More. 143 Cary Avenue, Originally Designed And Built By Award-winning Architect Garret Eakin In 2003, Is A Stunning Single-owner Abode Th...

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Photo of Listing #10776689

297 North Deere Park Drive, Highland Park, IL - $3,249,000

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 Van Bergan Home Has Been Meticulously Restored And Expanded. Van Bergan Is An Award Winning Architect Known For His Stone Exteriors, Studying And Working With Under Frank Lloyd Wr...

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Photo of Listing #10881571

143 Cary Avenue, Highland Park, IL - $3,200,000

Residential, Detached Single
  • 5 Beds
  • 9 Baths
  • 9,492 SQFT
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Timeless. Gracious. Private. A Stately, French Normandy-style Home In Sought After East Highland Park? Say No More. 143 Cary Avenue, Originally Designed And Built By Award-winning Architect Garret Eakin In 2003, Is A Stunning Single-owner Abode Th...

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3481 Bradley Court, Highland Park, IL - $3,200,000

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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2480 Sheridan Road, Highland Park, IL - $2,750,000

Residential, Detached Single
  • 7 Beds
  • 10 Baths
  • 8,682 SQFT
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New Price! Enjoy History's Charm Blended With Today's Technology. Bar None, The Best Finishes One Can Find On The North Shore. Located On Prestigious Sheridan Road. This Home Boasts A De Giulio Kitchen W/ Granite & Carrara Marble Counters, Ss App...

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Photo of Listing #10742637

330 Hazel Avenue, Highland Park, IL - $2,550,000

Residential, Detached Single
  • 7 Beds
  • 9 Baths
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Walk Up The Pathway To This Hampton's Style 7 Bed, 6 Full And 3 Half Bath Home. The Foyer Leads To The Formal Living Room With Fireplace, Office With Mahogany Built-ins, Family Room With Bay Window, 4-season Room, And Dining Room With Built-in Buf...

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Photo of Listing #10771178

1700 Meadow Lane, Highland Park, IL - $2,450,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
  • 7,204 SQFT
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Escape In Safety, Security And Privacy To A Gated 8 Acre Estate Hideaway In Highland Park, Il. Fortress Like With Foot Thick Floors And Reinforced Poured Concrete Walls, It Was Built As A Retreat In Event Of Health Issues And Social Unrest Similar...

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1773 Spruce Street, Highland Park, IL - $2,299,999

Residential, Detached Single
  • 5 Beds
  • 9 Baths
  • 6,500 SQFT
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Welcome To Your Own Private Retreat! This Sophisticated, Comfortable Family Home Offers 6500+ Sf On A Gorgeous 3/4 Acre Lot, Complete With Spectacular Built In Pool, Firepit, Covered Cabana W/outdoor Fireplace, And Pool House With Full Ba And Kit...

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Photo of Listing #10740990

212 Ravine Drive, Highland Park, IL - $2,195,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 4,825 SQFT
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Elegantly Remodeled Classic 5,000 Sqft Home In Prime East Highland Park Location Steps To Lake Michigan. 5 Bedroom 4.1 Bath Featuring The Finest Finishes, Architectural Details, And Flexible Floor Plan. First Floor Includes Gracious Foyer, Formal ...

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1653 Sunnyside Avenue, Highland Park, IL - $1,950,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 6,135 SQFT
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Custom Built 6 Bedroom, 5 1/2 Bath Home On Over 3/4 Acre In Desirable Sherwood Forest. Open Floor Plan With High-end Current Finishes & Upgrades Throughout. 1st Floor Features Formal Entry With Travertine Floor, Living Room With Fireplace, Spaciou...

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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 September 25th, 2020 at 7:30am CDT.