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.
Perfectly Located On Soughtafter Sheridan Road In The Heart Of Kenilworth, This Stately Redbrick Colonial Sits Quietly Behind A Circular Drive And Landscaped Gardens, Offering Wonderful Privacy On Nearly A Halfacre. Originally Built In 1918, The H...
A Sweeping Circular Drive Sets The Stage For This Residence, Where Art And Elegance Converge From The Moment You Arrive. The Entrance Is Graced By A Striking Custom Metal Sculpture By John Medwedeff, A Sophisticated Introduction To The Beauty With...
Where Does Modern Visionary Design, Flawless Transitional Execution, And Resort-style Living Collide All Together...only At 921 Sheridan. You Can Feel The Lake Breezes As You Dip Your Toes In The Pool That Highlights The Sensational Outdoor Living...
One Of The North Shore's Most Prestigious Addresses, 677 Sheridan Road, Is A Magnificent Estate That Seamlessly Blends Timeless Architectural Elegance With Modern Luxury Living. Situated Just Two Blocks From Lake Michigan, Glencoe Beach, Downtown ...
This Extraordinary Custom-built Residence Offers The Rare Combination Of Timeless Architecture, Modern Construction, And Award-winning Design. Built Just 26 Years Ago By Renowned Landmark Development Co., The Home Showcases Exceptional Craftsmansh...
CONTINGENT Classic All-brick Home On Prestigious Sheridan Road Offering Exceptional Space And Thoughtful Design Throughout. A Grand Foyer Welcomes You Into Oversized Formal Living And Dining Rooms Featuring High Ceilings And Expansive Windows That Fill The H...
It's Time To Unveil The Pinnacle Of Lakefront Living In Il, As This Newer Construction Estate Is Better Than Brand New Construction As It Encompasses Features That Could Never Be Built Today With The New Lakefront Building Ordinances. Try To Top T...
CONTINGENT Nestled In Leafy East Lakeview Is This Iconic 5 Br/4.1 Ba Chicago Greystone On A Massive 35' X 167.5' Lot, With Over 6,800 Sq. Ft. Of Finished Living Space. This Home Is Essentially New Construction Inside Of A Vintage Envelope. During Its Extensi...
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...
CONTINGENT Nestled On A Private Lane East Of Sheridan Road, This Distinguished Winnetka Residence Offers Privacy, Scale, Quality Craftsmanship, And Exceptional Everyday Livability In One Of The North Shore's Most Coveted East-side Locations. Designed For Ele...
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...
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Listing information last updated on August 15th, 2026 at 7:59am CDT.
