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Browse All Homes for Sale Along Chicago's North Shore, $3,000,000 - $5,000,000

$500,000 - $750,000 $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
Over $10,000,000
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Photo of Listing #12750752

22 Lakeview Terrace, Highland Park, IL - $3,900,000

Residential, Detached Single
  • 4 Beds
  • Baths
  • 5,500 SQFT
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Amazing Lakefront Property On End Cul De Sac Street!!! This Home Has Been Totally Remodeled And Meticulously Curated For Modern Living With Impeccable Design. The Expansive Floor Plan Features Four Generous Bedrooms, Each With Its Own En-suite Bat...

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285 W Westminster Avenue, Lake Forest, IL - $3,600,000

Residential, Detached Single
  • 7 Beds
  • Baths
  • 8,135 SQFT
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Rare Lake Forest Offering - Set On More Than Two Private Acres Bordering The Derwen Mawr Nature Preserve, This Exceptional Estate Represents One Of Lake Forest's Rarest Offerings-a Place Where Protected Open Lands, Resort-style Amenities, And Walk...

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1008 Bob O Link Road, Highland Park, IL - $3,450,000

Residential, Detached Single
  • 6 Beds
  • Baths
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Situated On A Prime Half-acre Lot In Sought-after East Highland Park, This One-of-a-kind Custom Residence, Completed In 2022, Offers A Rare Combination Of Timeless Architecture, Warm Contemporary Design, And Purposeful Functionality, All Executed ...

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400 Washington Road, Lake Forest, IL - $3,995,000

Residential, Detached Single
  • 6 Beds
  • 7 Baths
  • 8,991 SQFT
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Timeless Architecture, Extraordinary Scale, And An Exceptional East Lake Forest Lifestyle Come Together At 400 Washington Road. Set On A Beautifully Landscaped Acre Just Blocks From Lake Michigan, Lake Forest Beach, Historic Market Square, And Met...

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Photo of Listing #12672761 CONTINGENT

1 N Indian Hill Road, Winnetka, IL - $3,495,000

Residential, Detached Single
  • 6 Beds
  • 7 Baths
  • 5,894 SQFT
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Set On Over Half An Acre On Private Indian Hill Road Within The Sought-after Greeley School District, This Exceptional 6-bedroom, 6.2-bath Home Offers The Perfect Blend Of Timeless Elegance And Everyday Livability. Striking Curb Appeal Sets The To...

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414 Laurel Avenue, Wilmette, IL - $3,099,000

Residential, Detached Single
  • 6 Beds
  • Baths
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Beautiful New Construction Single-family Home In An Amazing Part Of East-wilmette Near Gilson Beach And The New Plaza De Lago Shopping Center. Designed For Elevated Living And Effortless Entertaining, This Home Offers Expansive Living, Dining, And...

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64 Crescent Drive, Glencoe, IL - $3,300,000

Residential, Detached Single
  • 6 Beds
  • Baths
  • 11.5k SQFT
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Simply Stunning! 20 Years Old Spectacular Brick & Limestone Gem Constructed By The Harness Group With 19 R00ms, 6 Bedrooms, 6 Full And 3 Half Bathrooms. 5 Zones Heating & A/c. Majestically Set Down A Winding East Glencoe Lane On Almost 3/4 Of An ...

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107 N Mayflower Road, Lake Forest, IL - $3,200,000

Residential, Detached Single
  • 3 Beds
  • 4 Baths
  • 4,505 SQFT
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A Rare Roy Binkley Architectural Masterpiece Set On 2.3 Private Acres, This Custom-designed California Contemporary Was Created In 1984 By Renowned Architect Roy Binkley. Impeccably Maintained, The Residence Showcases Timeless Design, Exceptional ...

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130 Maple Hill Road, Glencoe, IL - $3,690,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 6,872 SQFT
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You Have Truly Arrived! Welcome To 130 Maple Hill Road - An Extraordinary French Chateau Nestled In The Highly Sought After East Glencoe Community. Settled On The Beautiful Ravine, Breathtaking Views Await From Almost Every Window In This 3/4 Acre...

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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
  • 6 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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1128 Mt. Pleasant Road, Winnetka, IL - $4,200,000

Residential, Detached Single
  • 6 Beds
  • Baths
  • 6,950 SQFT
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Built To Impress, This Beautifully Designed, Custom Crafted Home Is Discreetly Tucked In Next To Crow Island Woods You Will Have Nature At Your Doorstep And Be Perfectly Situated On An Amazing Half-acre Lot. This Stunning 5 + Bedroom, 6.3 Bath Hom...

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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 September 8th, 2026 at 7:14am CDT.