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This estate, originally built in 1927 by architect Arthur Kelly in a Tudor Revival style, represented the pinnacle of architectural opulence. Hefner purchased it in 1971 for about $1.1 million (roughly $8.7 million today). The 21,000-square-foot mansion sat on 5.3 acres of prime land, boasting sprawling gardens and elaborate amenities.
Designed with entertaining in mind, it featured a grand central hall, a massive staircase, and richly decorated rooms with gold leaf accents, plush carpets, and elaborate woodwork. Hefner admired it for a space that could host large gatherings and elite soirées. Every detail was curated for maximum glamour, including a private wing for his Playboy Bunnies, and an Olympic-sized pool with an adjoining artificial cave—a recurring motif in his luxury estates.