Lakefront homes and historic mansions
Sheridan Road, an extension of Lake Shore Drive, is home to the most affluent communities on Chicago’s North Shore. Hugging the shores of Lake Michigan, the grand estates, some originally situated on 100 acres, were built between 1900 and the 1930s by the most prominent architects of the day, including Benjamin Marshall, Howard Van Doren Shaw, and David Adler.
The quick and scenic drive along Sheridan Road to Wilmette, Kenilworth, Winnetka, Glencoe, Highland Park, Lake Forest, and Lake Bluff offered prominent Chicago families weekend retreats with private beaches, stables, tennis courts, and guest houses. The European-inspired mansions with ballrooms, paneled libraries, and orangeries were replicas of Italian villas, English country homes, and French chateaux.
By the 1970s, the expansive lots began to be subdivided but many of the elegant mansions remained, retaining the grandeur of the Gilded Age. The lush and gated grounds and deep lots shield many of these grand homes as you meander along Sheridan Road, but you will never lose sight of the enduring appeal of Chicago’s North Shore.
443 Sheridan Road, Glencoe, IL - $18,000,000
233 Sheridan Road, Kenilworth, IL - $9,975,000
655 Sheridan Road, Glencoe, IL - $5,999,900
745 Sheridan Road, Winnetka, IL - $4,890,000
959 Sheridan Road, Highland Park, IL - $4,875,000
970 Sheridan Road, Glencoe, IL - $4,175,000
484 Sheridan Road, Glencoe, IL - $3,975,000
977 Sheridan Road, Winnetka, IL - $3,495,000
999 Sheridan Road, Highland Park, IL - $3,395,000
272 South Sheridan Road, Lake Forest, IL - $2,995,000
856 Sheridan Road, Winnetka, IL - $2,950,000
1119 North Sheridan Road, Lake Forest, IL - $2,850,000
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 March 4th, 2021 at 12:31pm CST.