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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
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Photo of Listing #12374916 CONTINGENT

870 Woodbine Road, Highland Park, IL - $1,299,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 4,896 SQFT
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**multiple Offers Received, Best And Final Offers Due Via Email, Sunday, June 8 At 5pm Cst** Looking For A Contemporary Home But Coming Up Short? This Is The One You've Been Waiting For. Don't Miss This Fully Renovated, Light-filled Modern Home Tu...

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Photo of Listing #12380883 CONTINGENT

3105 Warbler Place, Highland Park, IL - $922,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,914 SQFT
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Welcome To This Beautifully Maintained All-brick Colonial, Perched On A Hill At The Entrance Of A Friendly Cul-de-sac. With Timeless Curb Appeal And A Spacious 3-car Garage, This Home Offers A Blend Of Classic Beauty And Modern Comfort. Step Throu...

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Photo of Listing #12382002 CONTINGENT

1424 Glencoe Avenue, Highland Park, IL - $1,350,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 8,176 SQFT
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A Timeless Masterpiece In East Highland Park, Nestled On One Of The Area's Most Coveted Double Lots, This Opulent Residence Combines Exceptional Luxury With Modern Sophistication For Today's Most Desired Lifestyle. Impeccable Design + Details Comb...

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8 Heritage Drive, Highland Park, IL - $1,675,000

Residential, Detached Single
  • 3 Beds
  • 4 Baths
  • 2,825 SQFT
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Construction Is Already Underway On This Spectacular, Brand New Ranch Home In An Established, Maintenance-free Subdivision In The Perfect Highland Park Location And Cul-de-sac, As Part Of The Serenity At Heritage Development By Multigenerational B...

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Photo of Listing #12370090 CONTINGENT

137 Hiawatha Trail, Highland Park, IL - $829,800

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,200 SQFT
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Experience The Perfect Blend Of Comfort, Style, And Convenience In This Impeccably Renovated And Thoughtfully Expanded 4 Bedroom, 4 Bathroom Home, Nestled On Almost 1/2 An Acre In A Serene, Country-like Setting-yet Just Moments From Shops, The Met...

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3464 Old Mill Road, Highland Park, IL - $1,700,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 5,819 SQFT
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Welcome To 3464 Old Mill Road - A Masterfully Crafted Prairie-style Estate Inspired By Frank Lloyd Wright, Nestled On Over An Acre Of A Serene, Private, Tree-filled Landscape In Coveted Highland Park. With Over 9,000 Square Feet Of Livable Space, ...

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1672 Huntington Lane, Highland Park, IL - $1,399,999

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,216 SQFT
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New Construction In Coveted Sherwood Forest - Highland Park, Il. Experience Luxury Living In This Beautifully Crafted Single-family Home, Located In The Highly Sought-after Sherwood Forest Neighborhood Of Highland Park. Thoughtfully Designed By ...

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Photo of Listing #12361544 CONTINGENT

794 Dean Avenue, Highland Park, IL - $1,098,000

Residential, Detached Single
  • 6 Beds
  • 5 Baths
  • 4,185 SQFT
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Welcome To This Beautifully Updated Storybook Home Offering 6 Bedrooms, 4.5 Baths, And A Prime Location Directly Across From Ravinia Elementary And Just A Block From The Ravinia Business District. A Welcoming Covered Front Porch With A Swing, Sets...

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780 Highland Place, Highland Park, IL - $1,145,000

Residential, Detached Single
  • 5 Beds
  • 4 Baths
  • 4,201 SQFT
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This Spacious 2-story Home With A Great Mid Century Vibe, Is In A Highly Desirable Ravinia Neighborhood With Sidewalks, Wide Streets And A Short Walk To Ravinia, Chicago Botanic Gardens, Wonderful Shops And Restaurants And The Metra Train! This Gr...

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Photo of Listing #12361425 CONTINGENT

1951 York Lane, Highland Park, IL - $1,250,000

Residential, Detached Single
  • 4 Beds
  • 3 Baths
  • 2,894 SQFT
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Sitting On Over 1/3 Acre In Highland Park's Desirable Sherwood Forest Neighborhood, This Thoughtfully And Beautifully Renovated Mid-century Modern Ranch Offers 2,894 Square Feet On The Main Level, Plus A Newly Finished 500 Sq Ft Basement. The Home...

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Photo of Listing #12354274 CONTINGENT

419 Sheridan Road, Highland Park, IL - $800,000

Residential, Detached Single
  • 2 Beds
  • 2 Baths
  • 2,067 SQFT
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Welcome To This East Highland Park Ranch Home That Is Located On A Corner Lot And Only Steps From Ravinia Festival In Braeside. This Two Bedroom Spacious One Level Home Is Much Larger Than It Sounds With A Vaulted Great Room Addition. There Is A S...

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Photo of Listing #12364321 CONTINGENT

2018 Linden Avenue, Highland Park, IL - $899,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,222 SQFT
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If You're Looking For A Home In A Fabulous Walk To Town Location With Shopping, Restaurants, The Metra And The Lake And Beach Right At Your Door, Then This Is The House For You! This Home Combines Charm With Many Modern Updates And Is Perfect For ...

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Photo of Listing #12352361 CONTINGENT

441 Oakland Drive, Highland Park, IL - $1,150,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,335 SQFT
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Braeside Beauty On Established Tree Lined Street. Listen To Music From Ravinia On Your Charming Front Porch. If You Think The Outside Is Charming Wait Until You See The Inside! Large Kitchen With Island And Breakfast Bay Area. Kitchen Opens To Spa...

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Photo of Listing #12363028 CONTINGENT

186 South Deere Park Drive, Highland Park, IL - $990,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,976 SQFT
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Explore The Property Through An Immersive Virtual 3d Tour And Discover A Truly Unique Home. Nestled At 186 South Deer Park Drive, In Highland Park, Just Steps From Glencoe And Lake Michigan, This Exquisite 4-bedroom, 3 Full Bath, And 2 Half Bath R...

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Photo of Listing #12346514 CONTINGENT

1784 Reserve Court, Highland Park, IL - $1,649,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 4,690 SQFT
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Stunning Award-winning Orren Pickell Home On Nearly One Acre Features Luxury Living Throughout. The Exceptional 5-bedroom, 5.5-bathroom Custom Estate Has Oversized Rooms, Rich Architectural Details, 3 Indoor Fireplaces And Seamless Indoor-outdoor ...

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Photo of Listing #12350758

1857 Cloverdale Avenue, Highland Park, IL - $924,900

Residential, Detached Single
  • 4 Beds
  • 3 Baths
  • 3,108 SQFT
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Thoughtfully Updated Bright Four Bedroom Colonial In Sherwood Forest Ready For You Now. The Kitchen And All Baths Including The Powder Room Are Tastefully Renovated To The Highest Of Standards. The Kitchen Remodel Is Complete With Omega Cabinetry,...

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Photo of Listing #12349385 CONTINGENT

49 Red Oak Lane, Highland Park, IL - $995,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,936 SQFT
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Beautiful Red Brick Colonial Is A Family's Dream! Located On An Expansive Lot With A New Roof (2025), Gutters And Downspouts, Light Oak Hardwood Floors And Floor-to-ceiling Windows That Flood The Home With Natural Light. The Backyard Feels Like A ...

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215 Prospect Avenue, Highland Park, IL - $1,875,000

Residential, Detached Single
  • 6 Beds
  • 7 Baths
  • 5,000 SQFT
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Stunning Howard Van Doren Shaw English Arts And Crafts Home On Over An Acre Of Magnificently Landscaped Property, One And A Half Blocks From Lake Michigan. Fine Architectural Detailing Throughout, Including The 2017 Renovated Kitchen Completed Wit...

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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 June 19th, 2025 at 7:38pm CDT.