Before he moved in to his infamous L.A. bachelor pad, Hugh Hefner, the founder of Playboy, threw his swinging soirees at this Victorian-style estate. Designed by architect James Gamble Rogers in 1899, the handsome manse on Chicago’s Gold Coast was purchased by the Hef in 1959 and served as the original Playboy mansion until he moved to L.A. in the '70s. Today, the residence has been converted into luxe private condos, including Pamela Turbeville's glamorous, 3,900-square-foot unit. Pamela's home features a hand-lacquered dining room, three bedrooms and three baths.