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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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Photo of Listing #11133485

1869 Crescent Court, Highland Park, IL - $7,750,000

Residential, Detached Single
  • 7 Beds
  • 11 Baths
  • 10.1k SQFT
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Delight In Stunning Lake And Lush Garden Views From Dawn To Dusk From The Most Spectacular Property Available On Chicago's North Shore. This One-of-a-kind Property Is Comprised Of Nearly Four Acres Designed And Landscaped By Scott Bryon With A Aaa...

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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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2255 Egandale Road, Highland Park, IL - $5,125,000

Residential, Detached Single
  • 4 Beds
  • 10 Baths
  • 7,700 SQFT
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Sited On An Acre Of Gorgeous Lakefront Property (with 100' Of Crystal Blue Lakefront), This Newer Constructed 7700 Sf Home Is A Dream-home Like No Other. The Gorgeous And Lush Grounds (including An Inviting Indoor Pool With An Adjacent Hot Tub) R...

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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 - $4,475,000

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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1765 Lake Avenue, Highland Park, IL - $4,125,000

Residential, Detached Single
  • 8 Beds
  • 9 Baths
  • 9,557 SQFT
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Unparalleled Setting, Architecture, And Design Describe This 10,000 Sq.ft. Nantucket Inspired Timeless Beauty. Built In 1921, Recently Renovated And Expanded With The Finest Craftsmanship And Incredible Attention To Detail. Beautifully Situated On...

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140 Deere Park Court, Highland Park, IL - $3,999,999

Residential, Detached Single
  • 3 Beds
  • 6 Baths
  • 6,728 SQFT
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Spectacular Tony Grunsfeld Custom Home On A Quiet Cul-de-sac In East Highland Park. This Single-owner Home Is Meticulously Designed And Lovingly Maintained, Boasting Majestic Ravine Views From Every Room, Where Architecture And The Natural Landsca...

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Photo of Listing #10967469

2625 Mavor Lane, Highland Park, IL - $2,990,000

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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1419 Waverly Road, Highland Park, IL - $2,800,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 6,129 SQFT
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Click On The Virtual Tour And See The Whole House!!!private And Idyllic Is The Setting For This Over 6300 Sf English Country Home, Which Sits Majestically On Almost 1.5 Acres Of Ravine And Lake Views Property On One Of The Most Beautiful Streets I...

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3481 Bradley Court, Highland Park, IL - $2,750,000

Residential, Detached Single
  • 8 Beds
  • 7 Baths
  • 10.3k SQFT
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Beautiful Custom Built Home On Gorgeous Lot With Breathtaking Views Of The Conservancy And Lake Michigan. Grand Floor Plan With Gracious Room Sizes, Functional Living Spaces-perfect For Entertaining And Living. Chef's Kitchen With Gourmet Applianc...

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254 Hazel Avenue, Highland Park, IL - $2,250,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 8,000 SQFT
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Home Is On Breathtaking Approximately 1 Acre Ravine Property. Setting Has Unparalleled Views Thru-out, Fully Renovated With Quality High-end Finishes. A Sophisticated Tasteful Look And Feel In All Rooms. Gourmet Cooks Kitchen, Stainless Steel Appl...

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228 Maple Avenue, Highland Park, IL - $2,099,990

Residential, Detached Single
  • 4 Beds
  • 7 Baths
  • 6,058 SQFT
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Luxurious And Grand French Country Home In A Premier Location Just Two Blocks From Lake Michigan And Downtown Highland Park! Beautiful Circular Driveway Brings You To This Exceptional Stone And Stucco Home With Gorgeous Slate Roof. You Will Be Imp...

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1841 West Berkeley Road, Highland Park, IL - $2,000,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 5,000 SQFT
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Location, Quality, Price - Fabulous One Of A Kind Private 146 Ft Width 1/2 Acre Lot. Build A Spacious 94' Wide Floor `plan X 55'+ Depth Floor Plan. Plenty Room For A 4- Car Garage, Pool & Cabana. Enjoy You Property & Home Buffered With Over 70...

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Photo of Listing #11170677

3393 Old Mill Road, Highland Park, IL - $1,999,900

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 10k SQFT
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Magnificent 2.9 Acres Sets The Stage For This Better Than New Construction 10,000+ S.f. Home With Gorgeous Expanded Kitchen, Two-story Living Room, Infinity Pool, And Full-size Professional Basketball Gym. 5 Bedrooms, Including 2 Gorgeous Master B...

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1793 Reserve Court, Highland Park, IL - $1,875,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 6,092 SQFT
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This Home Is A Must See For The Serious Buyer!! Taxes Recently Lowered By Owner (~$35k)!----this Opulent Stone Masterpiece Sits In A Subdivision Of All Estate Homes, On A Lavishly Beautiful, Professionally Landscaped Lot. This Fabulous Estate Wi...

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Photo of Listing #11097792

124 Deere Park Court, Highland Park, IL - $1,799,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 5,957 SQFT
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This Wonderful East Braeside Home Features Breathtaking Ravine Views (including Seasonal Lake Views) And An Indoor Basketball Court! With Luxurious Finishes And Superior Craftsmanship, This All-brick Home Has A Beautiful Custom Kitchen With All Of...

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1499 Sheridan Road, Highland Park, IL - $1,750,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
  • 6,167 SQFT
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Rare And Rehabbed Elegant Victorian In A Prime East Highland Park Location. This Gracious Home Is Set On Nearly Three Quarters On An Acre And Features Many Spacious Rooms. 5 Bedrooms/4 Full And 2 Half Baths. Completely Refreshed For Todays Discern...

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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

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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 August 1st, 2021 at 6:00pm CDT.