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Homes for Sale in Highland Park, $3,000,000 - $5,000,000

$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 #12725476 CONTINGENT

1770 Sunnyside Avenue, Highland Park, IL - $3,299,000

Residential, Detached Single
  • 5 Beds
  • Baths
  • 9,385 SQFT
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Exceptional Custom-built Residence Completed In 2013, Where Timeless Architecture, Impeccable Craftsmanship, And Sophisticated Design Come Together In One Extraordinary Home. A True Standout Feature Is The Sought-after First-floor Primary Suite, O...

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2441 Woodbridge Lane, Highland Park, IL - $4,995,000

Residential, Detached Single
  • 9 Beds
  • 12½ Baths
  • 10.8k SQFT
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Situated On A Prestigious Private Lane In East Highland Park, This Rare Lakefront Offering Is A Mid-century Modern Masterpiece. Designed In 1957 By Renowned Architect Henry L. Newhouse Ii For Irving B. Harris, Chicago Philanthropist, This 10,000-s...

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966 Wade Street, Highland Park, IL - $4,399,000

Residential, Detached Single
  • 5 Beds
  • Baths
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New Construction Luxury Single-family Home Coming Soon To Highland Park Within Sought After Ravinia Elementary School Boundaries. Designed For Both Everyday Living And Elevated Entertaining, The Main Level Features A Private Home Office With Strik...

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22 Lakeview Terrace, Highland Park, IL - $4,400,000

Residential, Detached Single
  • 4 Beds
  • Baths
  • 5,500 SQFT
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Experience Unparalleled Luxury On The Lakefront. This 5,500 Sf New Construction Home Tucked Away At The End Of A Quiet Cul-de-sac Has Been Meticulously Curated For Modern Living With Impeccable Design. The Expansive Floor Plan Features Four Genero...

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Photo of Listing #12678290 CONTINGENT

2214 Churchill Lane, Highland Park, IL - $3,850,000

Residential, Detached Single
  • 5 Beds
  • 9 Baths
  • 10k SQFT
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Elegant And Sophisticated Custom Built 6 Bedroom, 7 Full And 4 Half Bath Home Located On 1 Acre That Is Reminiscent Of A Luxury Hotel Complete With Patio, Pool And Spa. This Limestone Clad Home Boasts Unsurpassed Quality Construction And Is Accomp...

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34 Logan Loop, Highland Park, IL - $3,800,000

Residential, Detached Single
  • 7 Beds
  • Baths
  • 7,891 SQFT
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Historic Lakefront Queen Anne Mansion On Lake Michigan! Set On A Private 3/4 Acre, Surrounded On Three Sides By Park, Ravine, And Lake, Adding "borrowed Landscape". Premier Location Within The "fort Sheridan" Neighborhood Of Highland Park, With Pa...

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Photo of Listing #12659749

2665 Bentley Road, Highland Park, IL - $4,399,900

Residential, Detached Single
  • 4 Beds
  • 7 Baths
  • 9,437 SQFT
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Sophisticated New Custom Built 5 Bedroom, 6 Full Bath & 2 Half Bath Home With Guest House, Patio, Pool & Spa Located On Over 3 Acres. This Limestone & Stucco Clad Home W/composite Terra Cotta Spanish Roof Tiles Boasts Unsurpassed Quality Construct...

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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 11th, 2026 at 3:44am CDT.