When you think of residential architecture in Chicago, several types of buildings come to mind immediately: bungalows, two-flats, worker cottages, courtyard apartments, and greystones. They have become symbols of the city itself, helping to define the character and look of our streetscapes. With more than 30,000 greystones found across Chicago, this construction style got its name from the locally sourced Bedford limestone quarried from south-central Indiana, which was used to create the structure’s front facade. During the period between 1890 and 1930, a significant number of greystones were built along the city’s historic boulevard system and in neighborhoods like Logan Square, East Garfield Park, and Kenwood, which is sometimes referred to as “the Greystone Belt.” The following greystones come in different sizes and design motifs with a little something for everyone — if you can afford it.

2121 W Pierce Ave, $3,999,999

Let’s start with the most expensive real estate listing. According to the Chicago Historic Resources Survey, this 6,600-square-foot residence on an oversized lot in Wicker Park was designed by architect Albert J. Fisher in 1907. The multi-million-dollar luxury property features a beautifully landscaped garden with an outdoor fireplace and an original two-story coach house that displays a sign bearing the name of the original owner, Paul P. Wenigman, who amassed his wealth through electric belts. I appreciate that the six-bedroom, five-bathroom home still has vintage details intact, such as crown moldings, fireplace mantels, and separate rooms, while also having all the modern updates expected with such a huge asking price.

538 W Deming Pl, $3,975,000

Nestled in the heart of Lincoln Park’s Arlington-Deming District is a stunning greystone originally built in the 1880s, before this area became part of Chicago (the annexation of Lake View Township did not occur until 1889). With its gorgeous historic exterior and spacious lot, there is much to love about this updated 6,000-square-foot house. It checks off all the luxurious features expected of such a high-priced property: a chef’s kitchen, a spa-like primary bedroom suite, a penthouse office with a roof deck, an outdoor space designed by Botanical Concepts, and a heated two-and-a-half car garage. 

1127 N Sacramento Ave, $2,200,000

Located on the historic boulevard system with direct views overlooking Humboldt Park, this 6,150-square-foot, single-family residence on a deep lot currently features four main bedrooms and four and a half bathrooms. Originally built as a two-flat for a wine importer in 1887, the historically preserved interior showcases woodwork, pocket doors, and an ornate staircase. The finished basement includes an extra bedroom with an ensuite bathroom and sitting room, a spacious family room with a wet bar, and laundry/utilities. Only five days after being listed for sale, this remarkable property is already contingent. 

2432 N Mozart St, $1,359,000

Logan Square is known for its blocks and blocks of greystones. This 3,566-square-foot residence, featuring five bedrooms and four and a half bathrooms, has been on sale since November. It was originally constructed in 1898 but has been renovated to accommodate the modern-day lifestyle. The first floor is completely open concept, while the upstairs primary bedroom includes an attached sitting room, office space, walk-in closet, and ensuite bathroom. It is located near all the attractions and amenities that Milwaukee Avenue and the surrounding area have to offer. 

17 E Scott St, $1,950,000

Last week, I shared the properties currently available on prestigious Astor Street. So let’s revisit the Gold Coast neighborhood with this nearly 4,000-square-foot residence on a quiet, tree-lined street. Behind the historic greystone facade, there is a reimagined contemporary living space that includes four bedrooms and four full bathrooms. A 20-foot-high glass window overlooks the south-facing tiered garden, which is adorned with flagstone steps and ivy-covered walls. The top floor of the property also features an additional outdoor space: a rooftop deck located right off one of the bedrooms.