The up-and-comingness of this West Side hipster haven was a bit of a controversial topic in researching this story. Some real estate agents claim that it’s done up and come, whereas others swear you can still find great values that will skyrocket down the line—thanks especially to the 606 trail, which opened last June.

There’s still a lot of unoccupied space in the sturdy old brick buildings, but people are catching on: Last year, the median sale price for houses jumped 66 percent, while condo prices shot up 184 percent, according to Midwest Real Estate Data. Crime is still high in the larger Humboldt Park community area, outside the eastern enclave: There were 46.3 violent crimes per 1,000 residents in 2015. That hasn’t stopped buyers from flocking to the 606 and its surroundings: In January, developer Perry Casalino announced plans to build houses there that start above $900,000; just three years ago, he told Crain’s he couldn't price similar houses above $500,000. “I feel like Humboldt Park is the band that I started listening to before the rest of my friends,” says teacher Zach Duffy, who moved there in 2012.