Chicago Properties Group/Business Insider
The loft is large by city standards, with three bedrooms and 3,300 square feet of space in a building in Chicago's Ukrainian Village neighborhood. It even has its own rooftop deck with a pool.
After being fired by the company in February 2013, Mason moved to San Francisco, recorded a full-length album, and sold his other Chicago property, a five-bedroom mansion in Evanston, Ill. The loft represents his last connection to the city where he founded Groupon.