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In 1959, with his magazine flourishing, Hefner acquired his first luxurious residence in the Gold Coast neighborhood of Chicago for roughly $370,000 (about $4 million today). Designed in a classic French style, the mansion was built in the early 20th century by esteemed architect James Gamble Rogers, known for designing Yale and Columbia University buildings.
This estate was Hefner’s playground, a hub of endless entertainment. He transformed it into a fantastical retreat, including a basement with a “submarine-view” pool and an artificial cave accessible only by swimming through a waterfall—an early hint at the themed extravagance to come. The home featured a double-height ballroom for lavish parties, weekly Playboy Bunny appearances, and guest suites for friends, artists, and celebrities.