Connect

Find us on...

Dashboard

Login using...

Homes for Sale in Highland Park, $5,000,000 - $10,000,000

$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
Map Save this Search
Sort listings by:Newest First
Photo of Listing #12395579

55 Prospect Avenue, Highland Park, IL - $5,995,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 9,000 SQFT
View details More Photos Save

Welcome To 55 Prospect Avenue-where Every Day Feels Like A Seaside Escape. Perfectly Sited On 1.5 Acres With An Extraordinary 175 Feet Of Private Lake Michigan Beachfront, This Coastal-inspired Estate Offers A Rare Blend Of Architectural Elegance,...

Midwest Real Estate Data LLC Logo

55 South Deere Park Drive, Highland Park, IL - $8,750,000

Residential, Detached Single
  • 5 Beds
  • 9 Baths
  • 9,749 SQFT
View details More Photos Save

This Extraordinary Lakefront Residence Is The Ultimate Blend Of Luxury, Comfort, Breathtaking Views And Private Beach. This Sophisticated Contemporary Home Boasts 9,749 Square Feet Above-grade And An Additional 4,434 Square Feet Of Finished Lower-...

Midwest Real Estate Data LLC Logo
Photo of Listing #12331011

2441 Woodbridge Lane, Highland Park, IL - $5,999,000

Residential, Detached Single
  • 9 Beds
  • 12 Baths
  • 10.8k SQFT
View details More Photos Save

Introducing An Exceptional Lakefront Residence On One Of Highland Park's Most Coveted Private Lanes. Set On A Masterfully Landscaped 1.85-acre Parcel, 2441 Woodbridge Lane Offers A Rare Combination Of Privacy, Scale, And Sophistication-backed By U...

Midwest Real Estate Data LLC Logo

147 Central Avenue, Highland Park, IL - $5,500,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 4,600 SQFT
View details More Photos Save

Discover A Rare Gem On Central Ave-this Stunning Victorian Historic Landmark Sprawls Over 4 Picturesque Acres, Just Steps From The Pristine Shores Of Lake Michigan. This Unique Property, Once Called The Cornelius Field House, Features A Beautifull...

Midwest Real Estate Data LLC Logo

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 July 17th, 2025 at 9:39am CDT.