Before he moved in to his infamous L.A. home, 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 the '70s. Today, the residence has been converted into luxe private condos, including Pamela Turbeville's glamorous, 3,900-square-foot unit. For more information about this property, please contact broker Susan Wagner of Rubloff Properties at 312.368.3281. Catch LXTV's Open House on Saturdays and Sundays on NBC. Check your local listings.