1316 N. Dearborn Parkway, Chicago | Minimum bid: $3.35 million | Auction on Dec. 3, 2019

This Gold Coast home was initially bought in 2014 for $4.2 million and has since been restored. Originally built in the late 1880s, the home features six bedrooms, an elevator with roof access and a coach house. It has multiple outdoor areas, including a rooftop terrace and ground-level backyard. The home goes up for auction on Dec. 3 with a starting bid of $3.35 million.