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Old Town Chicago Neighborhood

As the name suggests, Old Town has a rich history that dates back to Chicago’s earliest days, but today, and while the neighborhood does have a good sense of historical perspective, today it is one of the most sought-after residential communities in Chicago. Old Town wasn’t the first place in Chicago to be developed and settled; the actual reason that it was later given the title of “Old Town” is that the Great Chicago Fire that ravaged most of the city actually spared most of Old Town. Most of the neighborhood was spared, which is why many of the streets in Old Town are smaller and run counter to the patterns of the rest of Chicago’s “grid.” And because most of Old-Town predates the Chicago Fire, there are many interesting old landmarks in the neighborhood, like Saint Michael’s Church on Cleveland Avenue, which is actually one of only a handful of Churches in the city to have survived the fire.

In the middle of the 20th century, the neighborhood experienced an artistic renaissance that paralleled that of New York’s Greenwich Village. Because of cheap real estate costs, Old Town attracted artists and bohemians of all sorts in the 1950s, and it eventually became Chicago’s biggest outpost for hippies, which then attracted busloads of tourists. Like many bohemian enclaves, though, the changing social fabric of the neighborhood also attracted investors and developers, and the 1980s and ‘90s saw Old Town transform into a prosperous community of young professionals and families.

Now, Old Town bears more similarity to its surroundings – the Gold Coast and Lincoln Park – than it ever did before. While the face of the neighborhood is old and much of the place enjoys the protection of its landmark status, there’s also a modern touch to the residential real estate in the area, as several new mid-rise and walkup condo buildings have been built in recent years.

Because of the neighborhood’s popularity and its close proximity to River North and downtown Chicago, Old Town real estate tends to be fairly expensive. It is possible to find a small condo (studios or one-bedrooms) in the neighborhood between anywhere from $175,000 to $300,000, but the price for a mid-sized condo in Old Town tends to be a little bit more, averaging about a half million dollars. There is quite a bit of range in the neighborhood’s condo selection though, as hidden away in Old Town’s narrow streets you’ll encounter renovated old townhouses and duplexes that date back more than a century. Additionally, there are a number of condos priced more than $800,000 in Old Town that fall into the category of luxury real estate.

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