In the city of Chicago, Sheridan Road makes its way through various neighborhoods, then continues 20 miles north to the site of Fort Sheridan, passing by the properties featured below in Evanston, Wilmette, Winnetka, and Highland Park. The street and decommissioned military base are both named for General Philip Henry Sheridan, who helped save the city during the Great Chicago Fire of 1871. Sheridan Road evokes all kinds of memories for me personally, whether it was a route my family would take to cross the border into Wisconsin or to just gawk at all the beautiful homes in the affluent North Shore suburbs. You don’t have to get out of the car or leave your home to enjoy these amazing properties along the shores of Lake Michigan.
140 Sheridan Rd, Winnetka, $3,499,000
This is the type of home that comes to mind when you think of Sheridan Road. It was designed by North Shore architects Mayo and Mayo in 1925 for advertising executive Felix Lowy, who helped create the Lindbergh beacon atop the Palmolive Building on Chicago’s Michigan Avenue. Lowy’s stately Tudor Mansion originally extended 300 feet along Sheridan to Winnetka Avenue, but the home is still quite impressive today with its circular driveway, terraces, reflecting pool, and fountain. Inside is a grand two-story foyer surrounded by leaded glass bay windows with built-in window seats and massive stone fireplace followed by room after room of architectural magnificence.
721 Sheridan Rd, Evanston, $2,990,000
In Evanston, this Prairie Foursquare — designed by architect Thomas H. Mullay in 1909 — has maintained a lot of its historic beauty with some tasteful updates. It’s the former home of Mary Bartelme, who was not only the first woman judge elected to the Circuit Court but who also helped establish the Cook County Juvenile Court, the first of its kind in the U.S. What makes this residence stand out from the rest of the pack is its 55 feet of incredible private Lake Michigan frontage. You can enjoy the water views from the rear addition with roof deck, brick paved patio, and landscaped garden.
1500 Sheridan Rd UNIT 4I, Wilmette, $415,000
One of the most interesting parts of Sheridan Road was “No Man’s Land,” which was once described as “The Coney Island of the North Shore” with its various entertainments like the Miralago Ballroom and the Teatro del Lago movie palace. Wilmette annexed the unincorporated triangle of land and high-rise apartments gradually replaced the hot dog stands and gas stations along this stretch of Sheridan. At almost 2000 square feet, this lakefront condo comes with floor-to-ceiling windows and an enclosed balcony/sunroom to take in the views. There is a white kitchen that opens up to the dining room, while upstairs has two bedrooms plus a sitting room.
959 Sheridan Rd, Highland Park, $4,475,000
As much as Sheridan Road is full of history with its grand estates or nostalgic places like “No Man’s Land,” there are also plenty of newer mansions like this 2008 residence in Highland Park. Located right on the shoreline of Lake Michigan, the nearly 8,000-square-feet, six-bedroom, six-bathroom home is full of opulence with a custom built library, media room, and heated indoor pool. But that’s not even the best part. The owners can step right down to their own private beach as the property comes with 100 feet of lake frontage.
1124 Sheridan Rd, Evanston, $1,799,000
Back in Evanston to share with you this contemporary design by Thomas Hickey & Associates. At almost 5,000 square feet, the four-bedroom, eight-bathroom home feels even bigger with its angled ceilings and large windows. A unique atrium waterfall can be viewed from several rooms in the open floor plan of the home, while outside is a beautifully landscaped backyard with a blue-stone patio. Although not directly on the water like some of the other properties, this residence is just a block away from the park, beach, and running path along Lake Michigan.