Almost a year ago, I wrote about four homes for sale all designed by the architect Roscoe Harold Zook, who is best known for the Pickwick Theatre in suburban Park Ridge, as well as whimsical cottages straight out of a fairytale. This past month, the only Zook design in Chicago hit the market for the first time in more than 50 years. Most of his work is found in the Hinsdale area, where he lived and worked for most of his life, but he did have an office in downtown Chicago. So, who knows, there might be other examples of his solo work in the city that have yet to be discovered! (Though I may add, a couple of homes Zook did with his partner William F. McCaughey can be found in Norwood Park.)

According to Crain’s, the residence was originally built for Ralph Becker in the late 1930s, around the time the Edgebrook neighborhood was taking off. Elyse Mach, only its third owner, was a full-time music professor at nearby Northeastern Illinois University for 50 years (do I see a theme here?) who recently passed away. Now her home is for sale. I thought I’d see if I could find any other properties that were last sold many decades ago like Zook’s storybook-style house. I came across a good variety of real estate listings, including a Georgian, Victorian, mid-century modern, and Sears Kit Home.

6551 N Waukesha Ave, Chicago, $650,000

Located in Chicago’s Edgebrook neighborhood, the 1,900-square-foot Zook-designed house has many of the architect’s personal touches, including chevron patterns, intricate Lannon stonework, and a double-story living room with vaulted ceilings. And let’s not forget the famous “Zook roof” with wood shingles laid in a wavy, rolling pattern. Unfortunately there are no spiderweb motifs, which was one of his main signatures. The property features three bedrooms, two-and-a-half bathrooms, and a spacious backyard with stone patio.

4160 Raymond Ave, Brookfield, $419,000

Brookfield’s Congress Park is full of great historic homes, including several examples purchased directly from the Sears catalog. Sears Homes of Chicagoland confirms that this kit home is model No. 123, a Dutch Colonial design with a gambrel roof and a covered front porch. The 2,241-square-foot residence has been owned by the same family for close to 75 years. They purchased it from the original owners who constructed it in 1909. The interior is well maintained, looking much like it did way back then, and has four bedrooms on the second level.

9108 S Utica Ave, Evergreen Park, $314,900

Right on the border with Chicago is a 1940s double Georgian in Evergreen Park that has been maintained by its second owner for the last five decades. The nearly 3,000-square-foot, four-bedroom, two-bathroom home features a partially finished full basement and a large backyard with enough space to construct a garage if needed. It’s located near the Ashburn Metra station and Dan Ryan Woods. With a price drop earlier this month, the property is now contingent. 

502 E Washington St, Marengo, $384,900

Just 30 miles east of Rockford is the town of Marengo, where you will find quaint, historic homes like this 1885 Victorian. Maintained by the same owner for 50 years, the building is currently set up as a duplex, but it can easily be reverted back to its original function as a five-bedroom, two-bathroom single-family residence. The owner restored some of the rooms in the Eastlake style by preserving delicate woodwork and vintage light fixtures, as well as installing William Morris wallpaper above the grand staircase. Its plumbing, electrical, mechanical systems, and windows were replaced in 2005. 

8 Hunt Club Ln, Oak Brook, $1,800,000

Last but not least, a $1 million-plus ranch, originally built in 1970 and located in Paul Butler’s Oak Brook Estates, was put up for sale for the first time back in February. Set on two acres, the 4,895-square-foot residence has a sprawling interior that includes four bedrooms, three-and-a-half bathrooms, and a full basement with a second kitchen, a rec room, and a workshop. The outdoor space is perfect for entertaining family and friends as it has two covered patios, a built-in pool, hot tub, and beautiful landscaping with mature trees.