Purchased for a song at just $175,000 in 1965, the French chateau-style former home of pop crooner Bing Crosby is now on sale again for $40 million, a price that would break the Hillsborough real estate record that currently belongs to Elon Musk’s old house.  

20th Century radio and TV star Bing Crosby kicked the bucket way back in 1977, so we were surprised to learn that his wife Kathryn Crosby just died this past September. The decades-long gaps between their deaths maybe should not have been so surprising, his second wife Kathryn Crosby was 30 years younger than Bing. But her death set into place a series of events leading to the recent for-sale listing of the Crosby family’s longtime mansion in the ritzy San Mateo County enclave of Hillsborough. And the SF Business Times reports the 14,000-square-foot, five-acre French chateau-style mansion property is asking $40 million.  

Image via Sotheby's Realty

At that price, these pictures from the Sotheby’s Realty listing are about as close as any of us are going to get to that property. Obviously, there are some Bing Crosby artifacts shown with the property, which has 11 bedrooms. A piano on the property was used in Crosby’s 1956 film High Society, and the home is also where the Crosby clan shot a series of Minute Maid orange juice commercials in the 1960s. Let’s see some gin in that Minute Maid, Bing!

Crosby bought the property for $175,000 in 1965, which would only be about $2 million in today’s dollars, buying it from the son of the owner of the famed racehorse Seabiscuit. The architects were John Bakewell Jr. and Ernest Weihe, who did some architecture work on San Francisco City Hall, and the residence was completed in 1929.

Image via Sotheby's Realty

“This estate is truly one of a kind, blending Hollywood history, architectural grandeur and Northern California prestige,” Golden Gate Sotheby’s International Realty representative Jennifer Gilson told the Chronicle. “A property of this significance rarely comes to market, making it an extraordinary opportunity for the next owner."

Image via Sotheby's Realty

Wait, there’s an Elon Musk angle to this too? There is. Should this property actually sell for that $40 million asking price, it would be the most expensive home sale in the history of Hillsborough. The previous record was set in 2021 when Musk sold his Hillsborough home for $32 million, to an unknown buyer, when Elon was going through that phase where he was claiming he would sell “almost all physical possessions.”    

Related: Four-Bedroom Modern Mansion In Pacific Heights Hits Market for $38 Million [SFist]

Image via Sotheby's Realty