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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 #11396776

84 Sheridan Road, Highland Park, IL - $1,799,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 5,281 SQFT
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Wonderful East Braeside Brick Colonial On Close To A 1/2 Acre With Over 5200sf- Not Including The Huge Finished Basement. This Home Was Thoroughly Renovated And Expanded In 2011 And Features A Sun Filled Family Room With Vaulted Ceilings, Opening ...

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Photo of Listing #11410475

59 Sheridan Road, Highland Park, IL - $1,299,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,242 SQFT
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Beautiful Updated Home With 4000 Sq Ft Of Living Space In Prime East Location In Award Winning Braeside School District. Neutrally And Tastefully Decorated With An Abundance Of Natural Light And Stunning Views Of Ravine, Garden And Fabulous Wrap-a...

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Photo of Listing #11410348

750 Old Trail Road, Highland Park, IL - $1,000,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,580 SQFT
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This Well-maintained Home Offers A Perfect Floor Plan For Today's Buyer. Large Open Concept Kitchen Into Family Room. Kitchen Has All Newer High-end Appliances And Fabulous New Large Island, Plus Some Custom Stainless Cabinets. First Floor Also O...

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Photo of Listing #11409703

2365 Egandale Road, Highland Park, IL - $4,999,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 5,170 SQFT
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Designed By Renowned Architect Tony Grunsfeld, This Contemporary Masterpiece With 100 Feet Of Private Beach Sits On One Of The Most Coveted Private Streets In Highland Park. With Over 5,000 Square Feet Of Living Space Above Grade, This Designer Ho...

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Photo of Listing #11409247

2040 Kipling Court, Highland Park, IL - $1,080,000

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 With Newer Kitchen Appliances And Updated Bathrooms. Grand Double Doors Lead You Into...

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Photo of Listing #11406382

1780 Sunset Road, Highland Park, IL - $875,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 2,712 SQFT
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Prime Sunset Park Location With Gorgeous Park Views, This Newer Constructed 2 Story Colonial Is Perfect For So Many! Spacious And Airy, This Light Filled Home Offers An Ideal Open Floor Plan With A New Gourmet Kitchen Equipped With Stainless Steel...

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Photo of Listing #11403913

720 Ravinia Glen Place, Highland Park, IL - $1,650,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 4,859 SQFT
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This House Could Easily Be Featured In Architectural Digest Magazine! The Design And High-end Interior Finishes Are Beyond Spectacular! This Lovely Home Sits Up On A Half-acre Looking Over A Beautiful Vacant Wooded Lot That Cannot Be Built On. Fro...

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Photo of Listing #11406341

1887 Cooper Lane, Highland Park, IL - $1,099,900

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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1499 Sheridan Road, Highland Park, IL - $1,718,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
  • 6,167 SQFT
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Prime East Location For This Rehabbed Home With An Ideal Floor Plan. Located On Almost 3/4 Of An Acre, Beautifully Expanded And Renovated, There Is Over 6000 Sf Possessing Architectural Characteristics Combining Original Character Together With To...

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3505 Buena Road, Highland Park, IL - $950,000

Residential, Detached Single
  • 5 Beds
  • 4 Baths
  • 3,725 SQFT
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Meticulously Maintained Owner Build Home With 5 Bedrooms And 3.1 Bathrooms. The Home Is Nestled On Private Wooded 0.55 Acre Lot With Beautiful Natural Landscape. You Will Find Here Generous Room Sizes, Large Windows And Open Layout. Lower Level I...

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1436 Waverly Road, Highland Park, IL - $2,950,000

Residential, Detached Single
  • 6 Beds
  • 9 Baths
  • 10.1k SQFT
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Nestled On What Feels Like A Private Road In East Highland Park, Just A Block From The Lake, #1436 Sits High And Proud On A Promontory, With Seasonally Changing Views Of The Ravine On Two Edges Of The Property. High Ceilings Promote An Airy Feel T...

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514 Hill Street, Highland Park, IL - $1,250,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 4,212 SQFT
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Move Right In To This Custom Built Home With Exceptional Attention To Detail! From The Moment You Walk In And Sense The Volume Of The High Ceilings And See The Glass Transoms Above The Doors You Know This Is A One Of A Kind Home. The Abundance Of ...

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1845 Clavey Road, Highland Park, IL - $1,275,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 4,244 SQFT
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This Beautiful, Contemporary Highland Park Home Has Exactly What You're Looking For. Situated On Half An Acre And Teeming With Privacy, You'll Find The Layout And Space Of This Expanded Colonial Most Appealing. A Dramatic Two-story Foyer Greets Yo...

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3507 Bradley Court, Highland Park, IL - $1,498,888

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 5,701 SQFT
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3507 Bradley Court Is Situated On Top Of A Ravine In Fort Sheridan With Seasonal Views Of Lake Michigan. Enjoy Coveted Privacy On 1/2 Acre With Easy Trail Access To Lake Michigan. Open Floor Plan, High Ceilings, Windows Streaming Natural Light, F...

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Photo of Listing #11392912

1568 Cloverdale Avenue, Highland Park, IL - $849,000

Residential, Detached Single
  • 3 Beds
  • 3 Baths
  • 2,008 SQFT
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Sleek And Stylish Modern Ranch With An Abundance Of Light. This 3 Bed 2.1 Bath Home Features Walls Of Windows, High Ceilings, Skylights, Wood Floors, And Upscale Appliances. Seamlessly Connects Indoor And Outdoor Living. Enjoy The Peace And Privac...

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2445 Woodbridge Lane, Highland Park, IL - $6,595,000

Residential, Detached Single
  • 6 Beds
  • 7 Baths
  • 6,867 SQFT
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This Remarkable Home Is Set On A Private Lane With 1 1/2 Acres Of Land And Private Beach. This Is A One-of-a-kind Property. The Sprawling Lawn With Lovely Pool Leads To A Bluff Overlooking The Lake And The Glorious Lakefront. The Private Beach I...

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1486 Sunnyside Avenue, Highland Park, IL - $1,350,000

Residential, Detached Single
  • 4 Beds
  • 7 Baths
  • 4,770 SQFT
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This House Has It All! Custom Built To Last Through Generations With Attention To Every Detail And All The Spaces To Relax, Work And Play. Solid, Top Quality Construction From Top To Bottom Includes Wide Plank Hickory Floors Throughout, 10'+ Ceili...

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Photo of Listing #11380418

2111 Tennyson Lane, Highland Park, IL - $1,100,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 5,355 SQFT
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This 5355 Sq. Ft. Colonial On Almost 1 Acre Lot In The High Ridge Subdivision Is A Five Bedroom, Four And One-half Bath Knockout In Highland Park. Completely Rehabbed In 2012, This Home Is Situated On Nearly An Acre Of Land, With A Sprawling, Ful...

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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 May 22nd, 2022 at 8:23am CDT.