We are lucky that the Chicago area always has an impressive selection of architecturally significant residences for sale that are too good to miss out on. How can you resist properties with unique designs and interesting pedigrees, whether it’s a prairie-style school transformed into a single-family house or a midcentury modern nestled in the woods? Frank Lloyd Wright’s influence is evident throughout the area’s built environment. Almost all of the following homes have some kind of connection to the world famous architect: William Drummond was employed as his chief draftsman during their time in Oak Park, while Don Erickson apprenticed under Wright from 1948-51. According to its real estate listing, the original owner of our final home was an acoustical engineer who worked for a protégé of Wright’s. The one and only non-Wright home, commissioned by local artist Joan Steiner Kerman, was recently rehabbed by her own son who preserved its architectural integrity. 

3601 Forest Ave, Brookfield, $675,000

This William Drummond-designed home was originally built as a private kindergarten for education reformer and suffragist Queene F. Coonley in 1911. It was not in the greatest shape after a lender foreclosed on a previous owner. But now, almost seven years later and a jump in asking price (well above Brookfield’s average of $355,000), the historic property has come a long way with a sympathetic renovation that won the Kristin Visser Historical Preservation Award. The three-bedroom, three-bathroom home features an open floor plan, ideal for a contemporary lifestyle. Though Salt Creek runs through the backyard, the town has addressed flooding concerns with a mitigation program

1099 Fisher Ln, Winnetka, $1,590,000

Back in May, an almost 3,200-square-foot, glass-and-brick modernist residence was under contract, but the listing has since been reactivated. Located on a private street with views of the North Shore’s superb wooded ravines, this astonishingly intact 1960s midcentury modern with five bedrooms and four full bathrooms is the work of architect Don Erickson. His Jamaican-inspired roofs created tent-like ceilings inside, which are visible in the large living room with its prominent brick chimney and built-in seating. Skylights and clerestory windows bring additional light into the interior space, with a deck wrapping around the exterior.

130 N Dee Rd, Park Ridge, $2,090,000

Here is another Don Erickson-designed home that has been on and off the market for the past two years. It really takes a special kind of buyer to appreciate this one-of-a-kind architectural marvel (along with being able to afford the multi-million dollar asking price, of course). Originally built for developer Charles Matthies in 1958, the four-bedroom, four-bathroom residence projects over exclusive Murphy Lake and comes with 140 feet of water frontage. In addition to its cantilevered balcony, another cool detail is the “hanging” staircase that opens up directly to the home’s large living room.

9011 Keeler Ave, Skokie, $849,900

A 1,500-square-foot residence in Skokie is available on the market for the first time since its construction in 1956. The three-bedroom, three-bathroom home was originally designed by architect Don Schiller, who studied at the Illinois Institute of Technology and Yale University. Many of its vintage finishes survive, such as the tongue-and-groove redwood paneling and slate flooring. Yet the property is move-in ready with modern upgrades, including all-new plumbing with copper pipes, electrical, and heating. In addition to the new Marvin windows, the kitchen and bathrooms have also been renovated. I love the three-sided screened porch and wood deck.

5209 Lee Ave, Downers Grove, $825,000

Completely surrounded by nature, this 2,500-square-foot, three-bedroom, two-bathroom home is situated on over an acre of land in the Marshall Fields Woodlands section of Downers Grove. The property has been owned by the same family since it was built for original owner Lyle F. Yerges in 1953. The signature louvered airflow vents of architects Keck & Keck remain inside, along with floor-to-ceiling windows that take advantage of the views of the Maple Grove Forest Preserve, one of the oldest in DuPage County. After just one week on the market, this stunning property has already received multiple offers and is contingent as of this writing.