In 1965, Bing Crosby was already one of the most successful entertainers in American history when he purchased a sprawling estate in Hillsborough, California, for just $175,000. Sixty years later, the property would change hands again, this time for a staggering $25 million.
The sale marked the end of an extraordinary chapter for the Crosby family, which had held onto the Bay Area residence for six decades. The home, located in one of Northern California’s most exclusive communities, offered a rare combination of Hollywood history, expansive grounds, and old-world luxury.
“This estate is truly one of a kind, blending Hollywood history, architectural grandeur and Northern California prestige,” said Jennifer Gilson, who handled the sale for Golden Gate Sotheby’s International Realty. “A property of this significance rarely comes to market, making it an extraordinary opportunity for the next owner. … It embodies a level of elegance and privacy that is nearly impossible to replicate today.”
Crosby purchased the property with his second wife, Kathryn Crosby, who remained closely connected to the estate long after the legendary singer’s death in 1977. The residence became a family home for the couple and their three children, Harry, Mary, and Nathaniel Crosby.
The estate’s history actually began decades before Crosby moved in.
Built in 1929, the French château-style residence was designed by architects John Bakewell Jr. and Ernest Weihe. It originally belonged to a family associated with the legendary racehorse Seabiscuit, whose remarkable racing career became one of the great sporting stories of the 1930s.
Crosby’s purchase brought a different kind of fame to the property.
Spread across approximately five acres, the estate features an imposing mansion with 11 bedrooms, elaborate architectural details, and expansive grounds. The family filled the residence with personal memorabilia, including photographs, gold records, and reminders of Crosby’s extraordinary entertainment career.
Among its most distinctive features was a piano used in Crosby’s 1956 musical film, High Society. His office also featured wood paneling from Hearst Castle, while some of his famous hats remained on display. The family even filmed Minute Maid orange juice commercials at the property during the 1960s.
“He spent a lot of time at home with us,” Harry Crosby told SFGate. “He was on the road less in the ’60s, when I grew up, than he had been in previous decades. […] He would actually startle our neighbors by taking the family out caroling. People would open their front doors and there would be Bing Crosby and family serenading them with Christmas carols.”
Crosby died in 1977, but Kathryn continued living at the estate for decades. Following her death in September 2024, the family prepared to sell the longtime residence. In March 2025, the property entered the market with an ambitious $40 million asking price. Had it sold for that amount, it would have surpassed the previous Hillsborough residential sales record of $32 million, set by a property formerly owned by Elon Musk.
Instead, the estate sold for $25 million in June 2025, still an extraordinary increase over Crosby’s original purchase price.
“It’s difficult to turn the page emotionally, but all good things come to an end,” Harry Crosby told the Wall Street Journal.
For six decades, the estate served as a private connection to one of the 20th century’s most celebrated entertainers. Its sale closed a remarkable chapter in the Crosby family’s history, while ensuring that the mansion—and its Hollywood legacy—would continue under new ownership.
Related: In 1988, Tom Selleck paid about $5 million for a 63-acre Ventura County ranch once owned by Dean Martin; its avocado trees nearly died in a drought but still yield a small crop
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