Posted by Linda Shaughnessy on Sunday, October 4th, 2020 at 10:45pm.
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.
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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.
New Lakefront Magnificent Transitional Home With Approximately 17,000 Square Feet Finished Space. This House Has Oversized Windows With Nonrestricted Lake Vews And A Future Private Beach.exterior Is Constructed Of Stone And Limestone With Slate Ro...
Enjoy The Charm Of Living Just Steps Away From Lake Michigan In This Beautifully Designed And Expertly Maintained Property. Featuring Generous Living Spaces, Expert Craftmanship, A Bountiful Garden That Continuously Blooms With The Changing Season...
Nestled On A Private Lane East Of Sheridan Road, This Distinguished Residence Combines Timeless Sophistication With Everyday Livability. With Over 6 Bedrooms (including An In-law/guest Suite) And 7.1 Baths, The Home Is Designed To Accommodate A Va...
CONTINGENT A Rare Lakefront Opportunity In Kenilworth, Set On Nearly Three Quarters Of An Acre, Features Exceptional Table Land, A Well-preserved Bluff With A Winding Path To The Lake, And A Private Lakefront! Designed By Keck And Keck In 1957, This One-leve...
East Winnetka One-of-a-kind Home With Private Beach Access. Tucked Away On An Exclusive Private Lane, This Exceptional East Winnetka Residence Offers A Rare Opportunity To Enjoy Privacy And Luxury At Its Finest. Recently Renovated, 5 Bedrooms, 3...
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...
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Listing information last updated on December 4th, 2025 at 11:38pm CST.
