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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 - $7,500,000

Residential, Detached Single
  • 7 Beds
  • 11 Baths
  • 10.1k SQFT
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This Is Your Last Opportunity To Purchase This 10,000+ Sqft Home Set On Nearly Four Acres On The Lake. In The Next Month, The House Is Coming Down And This Trophy Property Will Be Divided And Sold As Three Buildable Lakefront Lots. Designed By Ton...

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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 #11177761

2255 Egandale Road, Highland Park, IL - $4,995,000

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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1261 Clavey Road, Highland Park, IL - $2,850,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 4,582 SQFT
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Over The River And Through The Woods To One Of The Most Special And Exclusive Nature Preserves And Homes In Highland Park. An Extraordinarily Private Sanctuary With A Sprawling Brick Ranch Home And 3 Car Garage. Renovate This House Or Create Your ...

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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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Photo of Listing #11107319

1419 Waverly Road, Highland Park, IL - $2,450,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 6,129 SQFT
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Private And Idyllic Is The Setting For This Over 6300 Sf English Country Home. This Home Sits Majestically On Top Of A Bluff And Ravine Of Almost 1.5 Acres On One Of The Most Beautiful Streets In East Highland Park. The First Floor Features An Up...

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334 Orchard Lane, Highland Park, IL - $2,350,000

Residential, Detached Single
  • 6 Beds
  • 8 Baths
  • 7,850 SQFT
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Breathtaking From The Moment You Pull Up To This Show Stopper 3 Story Home Located In East Highland Park! This Home Was Recently Renovated To Update The Kitchen, Bathrooms, And Every Other Room In The Home! This Expansive And Well Thought Out Layo...

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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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1805 Clavey Road, Highland Park, IL - $1,850,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 6,598 SQFT
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Modern Elegance Is Yours To Be Had In This 6600 Square Foot Brick Contemporary Nestled On A Private 1.39 Acre Professionally Landscaped Setting - Perfect For Family Life And Entertaining. Every Detail Has Been Curated To Highlight The Home's Wrap ...

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Photo of Listing #11126302

1793 Reserve Court, Highland Park, IL - $1,799,000

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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951 Fairview Road, Highland Park, IL - $1,600,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 4,332 SQFT
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Almost Completely New Construction In East Highland Park. This Gracious Home Will Boast Inviting Natural Light And High Ceilings With Over 5800 Square Feet Of Living Space, Including The Finished Basement. Formal Living Room Can Also Be Used As A ...

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1365 Sheridan Road, Highland Park, IL - $1,595,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 4,792 SQFT
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Iconic Highland Park Estate On Sheridan Road Available For First Time In 40 Years! This Spectacular 5-bedroom, 3.2-bathroom Brick Georgian Sits On Approximately One Acre Of Land, And Features Over 6500 Square Feet Of Living Space And An In-ground ...

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Photo of Listing #11153823

160 Linden Park Place, Highland Park, IL - $1,495,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 5,803 SQFT
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Beautiful Prairie Style Home Designed By George Maher In 1905, Sensitively Updated, And Restored By Award-winning Owners. The Home, Known As The Emil Rudolph Residence, Sits On Nearly An Acre Of Land On A Quiet Cul-de-sac, Just A Short Walk Down T...

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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 October 23rd, 2021 at 3:07pm CDT.