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The original Playboy Mansion was a 70-room classical French brick and limestone residence in Chicago at 1340 North State Parkway, which had been built in 1899 for Dr. George Swift Isham In Chicago's Gold Coast, it was acquired by Hefner in 1959. The mansion's basement, Hefner's original "grotto", had a swimming pool with a glass wall.
For a period in the 1970s, Hefner divided his time between the Chicago mansion and the Mansion West, moving full-time to the California mansion in 1974. The Chicago mansion boasted a brass plate on the door with the Latin inscription Si Non Oscillas, Noli Tintinnare ("If you don't swing, don't ring").
After Hefner left Chicago permanently for the coast after being hassled over alleged cocaine usage by James R. Thompson, the Chicago mansion was turned into a dormitory for the School of the Art Institute. In 1993, the mansion was gutted and turned into four high-price luxury condos. In 2011, one 7,874 square-foot condo was put on the market for an asking price of $6.7 million.