Playboy Mansion: The Story of Hugh Hefner's Two Houses

Two houses have carried the name. The first was a 1903 mansion in a grand, classical French style in Chicago's Gold Coast that Hugh Hefner bought in 1959, six years after he launched the magazine. The second, the one most people mean, is a 1927 half-timbered, Tudor-style house in Holmby Hills, Los Angeles, that Playboy Enterprises bought in 1971. Hefner died there on September 27, 2017, at 91, of natural causes, according to Playboy's announcement, as KERO 23ABC reported.

Neither house belongs to the Hefner side anymore. The Chicago building has been private condominiums since the 1990s. The Los Angeles house was sold in 2016 to Daren Metropoulos, who agreed to let Hefner live out his life in it, and who began renovating it in 2019 under a city covenant that bars him from tearing it down.

Hefner's longest address was the Los Angeles one, his home from the 1970s until the day he died, and it is where this story mostly lives: Hugh Hefner's former Holmby Hills mansion, a department-store heir's house before it was anyone's party.

The first Playboy Mansion, Chicago (former)

Hefner bought the Gold Coast house in 1959 and made it the first house to carry the Playboy name. WTTW's Chicago Stories describes what he put inside it: a brass plaque in Latin at the gate, a bowling alley, and a fireman's pole that dropped from the living room to an underground pool, with a window from the bar looking into the water.

He left for California in 1974, by the accounts of Time Out Chicago and Chicago Star Media. The building outlived its purpose. In 1984 Playboy leased the empty mansion to the School of the Art Institute of Chicago for $10 a year, according to Chicago Star Media, and in 1993 it went to a developer who divided it into condominiums.

That is what Hefner's former Chicago mansion, the original Playboy Mansion has been ever since: a home to the people who own its units. You see it from the public sidewalk, facade and gate included, and no further.

A department-store heir's house

The Los Angeles house was not built for parties. The firm of Joseph Estep and Arthur Rolland Kelly designed it in the mid-1920s for Arthur Letts Jr., son of the founder of the Broadway department stores, and it was finished in 1927, per the University of Washington's Pacific Coast Architecture Database. The elder Letts had laid out Holmby Hills on the old Wolfskill Ranch, and his son's estate took in this house and a sister house built two years later, in 1929, about 7.3 acres in all, according to the release announcing the sale.

After World War II it belonged to the inventor Louis D. Statham, who extensively altered it in 1947.

The house sits on about five acres, and the Los Angeles County Assessor still dates it to 1927. Even the county's own figures treat the land as the main asset: it is assessed at more than 12 times the value of the house.

The company's house

Playboy Enterprises, the company, bought the estate in 1971, according to Beverly Press; NBC News put the purchase about 45 years before the 2016 sale. The architecture database credits Hefner himself, so the record is not uniform. In January 2016 it was the company and not Hefner that put the mansion on the market, with one unusual condition attached: whoever bought it had to let Hefner keep living there for the rest of his life. The buyer turned out to be the neighbor. Daren Metropoulos had owned the 1929 sister house next door since 2009, according to the release announcing the sale, and he closed in August 2016 with the life tenancy in place.

The tenancy lasted 13 months.

Allegations and a verdict

Two later accounts tied the house to allegations of abuse and coercion.

In January 2022, A&E's 10-part docuseries about Playboy gave former residents a hearing. Holly Madison, who lived in the house as one of Hefner's girlfriends, said she thinks it was “cult-like” and that the women were “gaslit” into seeing Hefner as a good man, as NBC San Diego reported. Playboy answered in a statement that “the Hefner family is no longer associated with Playboy, and today's Playboy is not Hugh Hefner's Playboy,” and that it trusts and validates the women and their stories, as NBC San Diego reported. His son Cooper Hefner defended him on Twitter, calling the accounts “a case study of regret becoming revenge,” as Fox News and NBC San Diego both reported. No court has ruled on the docuseries accounts, and Hefner died more than four years before they aired.

On June 21, 2022, a Los Angeles County civil jury in Santa Monica found that Bill Cosby had sexually abused a 16-year-old girl at the mansion in 1975, and awarded her $500,000, as CBS News and NBC reported. Cosby has denied the allegation.

The covenant and the rebuild

After Hefner's death, Los Angeles City Councilman Paul Koretz moved to seek landmark status for the house. That motion never reached a vote. In its place, Koretz and Metropoulos announced on March 6, 2018, a signed covenant: Metropoulos would not demolish the main house, would repair and keep up its facade through his renovation, and the promise would bind any later owner too, Beverly Press and Bisnow reported. In plain terms, the house got a landmark's main protection without the landmark process, and, as Bisnow noted, the deal let Metropoulos start renovating sooner than a designation would have.

Metropoulos began filing renovation permits in July 2019, according to TMZ, and its aerial photos in September 2021 showed the plastic sheeting was off the roofs and the grotto still being reworked. His stated aim, according to the release announcing the sale, was to reconnect the two Letts houses and return the 7.3-acre estate to the vision of its architect, Arthur R. Kelly. No source we found says whether the renovation is finished.

More Los Angeles front doors

Start with celebrity homes in Los Angeles.