The following properties have not been for sale in a very long time. They either had the same owner for several decades or were passed through the family for several generations. For instance, a prairie-style residence in Berwyn came to the market for the first time since it was constructed 117 years ago. The home’s architects, Tallmadge and Watson, first met when both were employed as draftsmen in Daniel Burnham’s office. Tallmadge is credited with coining the term “Chicago School,” which is still used to describe the progressive commercial and residential architectural work that was done in the city during the late 19th and early 20th centuries. This home and four other interesting residences that follow fall perfectly in the “it’s been a long time” category.   

3131 Wisconsin Ave, Berwyn, $799,900

The Tallmadge and Watson-designed home on a huge lot in Berwyn is currently set up as two separate apartments (numerous additions were done by the same architects who kept all the original details). Hopefully this listing will attract a preservation-minded owner looking for a “new” project, and who can deconvert it and bring this historic design back to life. Although changes were made, the interior is intact with art glass doors and windows, as well as beautiful quarter-sawn oak wood. Carpets have protected the vintage hardwood floors, and the home has a new roof, furnace, and hot water heater. 

5804-08 N Magnolia Ave, Chicago, $1,450,000

On a triangular corner lot in Chicago’s Edgewater is a beautiful Victorian that has been in the same family for 60 years. The historic main residence with four bedrooms and three bathrooms has been well maintained with beautiful woodwork throughout the interior. That ceiling! Those pocket doors! It’s also been updated with a new kitchen, wiring, and piping, and more. Across the backyard is a coach house with two units that can be combined. 

8 S Beach Ave, Beverly Shores, IN, $975,000

Crossing the state border into Indiana to share this 1970s home in the lakefront community of Beverly Shores, which is looking for its second owner. The 2,685-square-foot two-bedroom, two-bathroom residence is situated on almost an acre of land at the peak of a sand dune and comes with multiple decks to take advantage of the views. The outdoor space also includes terraced plantings, ponds, gardens, and a separate screened room. Plus, the 1933 Century of Progress Homes and Indiana Dunes State Park are steps away.

17N501 Sleepy Hollow Rd, Dundee, $550,000

Alfred P. Shaw, a junior partner in the firm of Graham, Anderson, Probst & White, worked as the chief architect on one of their most famous projects, the Merchandise Mart. In the 1940s, he built a weekend home for his family on a private road in West Dundee. The modernist three-bedroom, one-bathroom residence has glass windows that look over a small inground pool and the property’s protected natural surroundings. First listed for sale back in June, it returned to the market with a price cut and is presently contingent. 

6535 18th St, Berwyn, $449,900

With only two owners since it was built in 1957, this nearly 3,000-square-foot split-level on a corner lot in North Berwyn is like stepping back in time. The preserved interior includes linoleum floors, formica countertops in the original kitchen, wood-paneled walls, an original built-in grill in the breezeway, and cedar-lined closets in the bedrooms. And you’ll feel completely nostalgic with the untouched basement and its original tiki wet bar. The home comes with four bedrooms and two and a half bathrooms. (Vintage furniture is not included.)