While searching through various real estate search engines, I was surprised there were no properties currently on the market by the world-famous architect Frank Lloyd Wright. Directly west of Chicago’s border, the historic suburb of Oak Park has 25 buildings either designed or remodeled by Wright while he lived and worked there at the start of his long architectural career. Although disappointed, I found a number of interesting listings available at the moment in Oak Park, including a property with a notorious past and one with a connection to Wright. But there is more to the town than just its celebrated history and architecture. Besides easy access to the city by train or car, the town boasts a legendary record store, an amazing independent bookshop, some great food establishments (may I recommend the Daly Bagel?), and pretty parks. Oak Park deserves its reputation not just as a locale worth checking out as a visitor, but as a place to call home.

1147 Wenonah Ave, Oak Park, $1,100,000

While this 1920s five-bedroom, five-bathroom brick bungalow on a large corner lot in South Oak Park might look attractive to prospective buyers, the home comes with an infamous backstory. This is the former residence of Chicago Outfit boss Sam Giancana, who lived here for nearly 30 years and was gunned down in the basement in 1975. While that space is now used as a yoga studio and the kitchen has been updated, many of the house’s original elements survive like its clay tile roof, metal canopies, leaded glass windows, limestone fireplace, and vintage black and green bathroom. With a $1.1 million price tag that fits its legendary status, the elaborate home is on the market for the first time since 1991.

​​917 Chicago Ave, Oak Park, $835,000

Located just a few doors down from the Frank Lloyd Wright Home & Studio is this 3,621-square-foot four-bedroom, three-bathroom Queen Anne originally built in 1894. The house’s first owners Thomas and Jane Worswick have a connection to the early days of Oak Park. Jane was the daughter of Joseph and Betty Kettlestrings, the first white settlers here in 1837, who operated an inn that served as a stagecoach stop on the route from Chicago to Galena. On sale for $835,000, the home is a mix of old and new with original pocket doors and ornate wood details while many of the spaces have been fully renovated, like the new kitchen and third-floor family room/guest suite. With some finishing touches, the basement has potential for more bedrooms and bathrooms. 

140 Francisco Ter, Oak Park, $318,000

Frank Lloyd Wright’s Francisco Terrace was a multi-family apartment complex built in 1895 on Chicago’s West Side. When it was torn down in 1974, architect Ben Weese salvaged the terra cotta arch, cornice, and decorative panels. Four years later, his brother Harry Weese reincorporated the elements into a new structure in Oak Park based on Wright’s design. Listed at $318,000, this three-bedroom, three-bathroom townhouse is spread over four levels of living space that includes a rooftop deck. It’s walking distance to public transportation as well as Oak Park’s shopping and restaurant area, the Hemingway District.

732 N Cuyler Ave, Oak Park, $525,000

Currently on the market for $525,000 is this adorable three-bedroom, three-bathroom bungalow. It’s full of charm wherever you look, like the coffered ceiling in the dining room or the butcher block counters and cork flooring in the kitchen. The finished basement features a concrete epoxy shine floor, while the outdoor space has a private brick and stone patio hidden behind a pergola. Though an older home, there have been plenty of updates over the years like the addition of a high-efficiency York Furnace in 2021, a new roof in 2019, and custom Gilkey windows. It’s located near Whittier Elementary School and Oak Park Public Library’s Dole Branch. 

204 Harrison St, Oak Park, $550,000

While Oak Park might be known for its older residences, there has been a building boom over the last decade. New development resulted in Oak Park taking over Chicago as having the most rental units in the state. Located in the middle of Oak Park’s Arts District, you’ll find an example of that “newer” construction, specifically this 2,417-square-foot, three-bedroom, two-and-a-half-bathroom townhouse that dates from 2018. As a  FlexHouse, meaning it is specially zoned for both residential and business, here is a perfect opportunity to work where you live. It comes with an open concept floor plan, heated concrete floors, a fenced-in backyard space, and two-car garage.