Browse All Homes for Sale Along Chicago's North Shore, $5,000,000 - $10,000,000
$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 |
139 Sheridan Road, Winnetka, IL - $9,499,900
Summer Is Right Around The Corner, And 139 Sheridan Is The Ultimate Lakefront Escape. Built Into The Bluff And Just Steps To The Water, This Turnkey Morgante Wilson Custom Home Is Designed For Effortless Lake Living. One Of The Last New Constructi...

2441 Woodbridge Lane, Highland Park, IL - $6,900,000
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...

959 Sheridan Road, Highland Park, IL - $5,750,000
Experience Coastal Elegance On Lake Michigan, Perfectly Situated On 1 Acre In East Highland Park With 100 Feet Of Private Sandy Beach. All Bluff Work Just Completed By Top North Shore Engineers! Wake Up To Breathtaking Sunrises And Unobstructed La...

624 Pine Lane, Winnetka, IL - $5,995,000
Welcome To This Stunning Custom Home Designed By Morgante Wilson, With Thoughtful Input From Discerning Owners. This Once In A Lifetime Home Is Nestled On A Picturesque 0.86-acre Lot On Private Pine Lane Near Schools, Town And Train. This Thoughtf...

140 Sheridan Road, Winnetka, IL - $9,999,500
This Is The North Shore's Most Regal Restoration To Ever Come On The Market With A Captivating, Majestic Presence Set On A Rare 1 Plus-acre Lot That Also Includes A Buildable Lot For A 2nd Structure To Create The Ultimate East Winnetka Estate. Thi...

111 Mayflower Road, Lake Forest, IL - $6,250,000
Rare Opportunity To Own This Beautiful Lakefront Home On 4.11 Acres W/ 300' Of Lake Michigan Shoreline On Coveted Mayflower Road. Located Down A Tree-lined Driveway At The End Of A Private Lane, This Stately Brick Home Was Built In 1914 And Featur...

261 East Onwentsia Road, Lake Forest, IL - $7,250,000
This Stunning East Lake Forest Estate Combines Elegant Architecture With Natural Beauty, Sitting On Nearly Three Gated Acres In The Heart Of Town. Designed In Collaboration With The Renowned Architect Darcy Bonner In 2010 It's A Perfect Blend Of S...

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

794 Greenwood Avenue, Glencoe, IL - $5,275,000
New Magnificent Transitional Home With Approximately 9,000 Square Feet Finished Space. Exterior Is Constructed Of Brick And Limestone With Slate Roof Which Represents Timeless Construction On One Of The Most Picturesque Streets In Glencoe. Close T...

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 April 29th, 2025 at 1:23pm CDT.