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5 most expensive homes for sale in Chicago right now

Written by
Clayton Guse
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Chicago's real estate market is nothing like that of New York or Los Angeles. Our downtown area isn't saturated with $1 million apartments, and most of the super expensive homes in the region are located in the suburbs. Still, there are plenty of bourgeois pads in Chicago proper that are capable of making you green with envy.

Here are the five most expensive homes currently for sale in the city. 

5. 415 E North Water St, Ph 05 — $12.95 million

If this two-floor riverfront penthouse looks like something out of Empire, it's because the Fox show tapped the place as a shooting location. With an in-unit basketball court, a 500-gallon hot tub, three saltwater aquariums and a 67-foot wraparound terrace, it seems like it'd be up to Lucious Lyon's standards. 


4. 159 E Walton Place, Penthouse — $13.9 million

This three-floor, 12,000 square-foot penthouse in the Palmolive Building is owned by Chicago native Vince Vaughn, and he's been trying to sell the place for nearly five years. From 1965 to 1989, the space was occupied by the headquarters of Playboy Enterprises, which seems fitting for the "Frat Pack" member. Vaughn originally purchased it in 2006 for $12 million, and first put it up for sale in 2011 for an enormous $24.7 million. The price has dropped drastically since then, but the penthouse still can't attract a buyer. 


3. 11 E Walton St, #5200 — $13.9 million

The Waldorf Astoria is a fancy place to stay, but it's an even nicer place to live. This 52nd-floor residence has all of the essentials for an eight-figure home: A wine cellar, a home theater, a private pool area and views of the city that will make you tinkle yourself. This spot is definitely reserved for someone who wants to feel like Chicago royalty 


2. 924 N Clark St — $15 million

It's hard to even imagine what it's like to live in a four-story Gold Coast home like this one, especially when you're sitting on a torn-up couch in a studio apartment. This mansion was built in 1916 and has been extensively renovated since. It has six bedrooms, 7.5 bathrooms, two kitchens, an elevator, a greenhouse and a four-car garage. It also has seven terraces, because why not?


1. 1516 N Lake Shore Drive — $17 million

The most expensive home currently on the market in Chicago is this French chateau-inspired stone beauty. It's a part of the historic Seven Houses on Lake Shore Drive District, and resembles something out of The Grand Budapest Hotel. The property boasts a marble staircase, a 2,400 square-foot coach house, stained glass windows and plenty more elitist decor that ought to make your life feel even less significant.

Photographs courtesy of Redfin 

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