Hugh Hefner's House (former), the original Playboy Mansion

Playboy founder Hugh Hefner bought this 1903 beaux-arts Gold Coast mansion in 1959 and made it the first Playboy Mansion. Art students came later, and it has been private condominiums since the 1990s.

WTTW’s Chicago Stories describes a brass Latin plaque at the gate, a bowling alley, and a fireman’s pole from the living room to the underground pool. A bar window looked into the pool.

Hefner paid $400,000 for the house, according to Chicago magazine’s 2018 report, republished by the Chicago Tribune. Chicago Star Media, writing in 2025, puts the 1959 price at $370,000.

In 1984, years after Hefner left for California, Playboy leased the empty mansion to the School of the Art Institute of Chicago for $10 a year. A developer paid $1.1M for it in 1993.

The building is private condominiums today, and residents live inside. You see it only from the public sidewalk, facade and gate included; the grounds are not open to visitors.