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 |
395 Greenleaf Avenue, Glencoe, IL - $5,900,000
Impeccable Showcase All Brick Home With Separate Coachhouse On .8 Acre Beautiful Property Located On Of The Finest Streets In East Glencoe. Featured In House Beautiful Magazine, The Main House Has Been Elegantly Renovated To Include Parisian Tile,...
1650 Green Bay Road, Lake Bluff, IL - $6,250,000
On The Market For The First Time In Nearly 50 Years, The Historic Phelps Kelley House Is One Of Lake Bluff's Most Significant Estate Properties. Designed In 1927 By Noted Chicago Architect Ambrose Cramer, A Protege Of David Adler, This Tudor Reviv...
CONTINGENT 788 East Woodland Road, Lake Forest, IL - $6,250,000
A Quintessential Lake Forest Manor With Storied Legacy And Timeless Elegance. Perched On 2.5 Acres Along Lake Road, This Iconic Lake Forest Estate Offers A Rare Blend Of Architectural Pedigree, Historical Significance, And Modern Refinement. Origi...
117 Belle Avenue, Highland Park, IL - $6,750,000
Located In The Coveted Belle Avenue Historic District, This Extraordinary Estate Sits On 2.3 Acres Of Manicured Grounds With Sweeping Lake Views. Fully Renovated And Expanded, The Residence Blends Timeless Elegance With Modern Luxury For A Truly O...
43 Indian Hill Road, Winnetka, IL - $7,275,000
New Magnificent Transitional Home Situated On 1 Acre Picturesque Lot With Approximately 15,000 Square Feet Finished Space. Exterior Is Constructed Of Stone And Limestone With Slate Roof Which Represents Timeless Construction. The House Features 6...
455 Sheridan Road, Kenilworth, IL - $5,975,000
New Magnificent Transitional Home With Approximately 11,000 Square Feet Finished Space. Exterior Is Constructed Of Brick And Limestone With Slate Roof Which Represents Timeless Construction. Close To Plaza Del Lago With Its Numerous Shops And Rest...
320 Woodley Road, Winnetka, IL - $5,149,000
Perfectly Nestled On One Of Winnetka's Finest Enclaves, This Stately 6-bedroom, 5.2-bath Georgian Estate Offers A Rare Fusion Of Architectural Elegance, Exceptional Craftsmanship, And Resort-style Amenities. Set On Nearly An Acre Of Meticulously M...
794 Greenwood Avenue, Glencoe, IL - $5,749,000
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...
261 East Onwentsia Road, Lake Forest, IL - $6,500,000
Nestled In The Heart Of East Lake Forest, This Exquisite Estate Seamlessly Blends Elegant Architecture With Natural Splendor, Set On Nearly Three Gated Acres. Crafted In Collaboration With The Esteemed Architect Darcy Bonner In 2010, It Epitomizes...
CONTINGENT 55 South Deere Park Drive, Highland Park, IL - $8,750,000
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-...
111 Mayflower Road, Lake Forest, IL - $6,250,000
Rare Opportunity To Own This Beautiful Lakefront Home On Almost 4 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 Fe...
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 12th, 2026 at 3:08pm CDT.
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