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Bing Crosby's White Christmas is the best-selling song of all time. He won an Oscar for Best Actor, for 1944's Going My Way. He had a love affair with Grace Kelly. His 'Road To' movies with Bob Hope are some of the best-loved comedy films of the 20th century. He made music with everyone from Bix Beiderbecke to David Bowie.
He even died in style: his last words were 'Great game of golf, fellas. Now let's go and have a Coca-Cola,' spoken immediately after walking off the 18th of a beautiful course in Spain, and immediately before the massive heart attack which brought his 74 years to a painlessly instantaneous close.
'I'm dreaming of a glittering career as an iconic entertainer...': Bing Crosby in his heyday.
He even had cool nicknames: known simply as 'Bing' to most around the world, he was dubbed 'Der Bingle' in Germany and (this is my favourite) 'El Bingo' in Spanish-speaking nations.
In the words of another 20th century music legend, 'some guys have all the luck'.
At the end of a day in his charmed life — perhaps after shooting the breeze with Louis Armstrong, having lunch with Frank Sinatra or playing golf with Clint Eastwood — Crosby would come back to his house at 1200 Armsby Drive, in the Bay Area city of Hillsborough, just south of San Francisco. That house is now for sale.
The ultimate crooner moved here in 1965 and lived here for the rest of his life; his wife, Kathryn, called it home until her own death in 2024.
The Crosby family sold the house, The Crosby Estate, for $25 million in the summer of 2025. But if you're sore at missing out back then, the good news is that it's back on the market, after a $3 million refurbishment, at $28.995 million via Jennifer Gilson of Golden Gate Sotheby's International Realty.
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It's a huge place, with 11 bedrooms, 15 bathrooms and over 18,500sq ft of space — but it's the style of the house that really wins us over. There are obvious elements borrowed from French chateaux (not least the grey slate roof turrets), but also an arched colonnade to lend an Italian flavour, and wood-panelled rooms and plasterwork which wouldn't look out of place in and English country house. Fittingly, it all feels like it could be a film set created in the heyday of Hollywood's Golden Age.
All this was the work of architects John Bakewell Jr. and Ernest Weihe, who built the house in 1929, creating a home which — in the words of the agent — blends 'grand architectural presence with a warm, liveable layout... designed for both intimate daily living and elegant entertaining'.
There's a string of beautiful reception rooms, including a strikingly pretty oval dining room with charming trompe-l'oeil to make the space feeel like a garden in springtime.
We also particularly love the home office, in one corner of the house and with lovely views of the gardens of just under two and a half acres — one of the largest plots in this neighbourhood.
It's unusual for a house to come back on the market so quickly, and for a relatively small price uplift in percentage terms, considering the scale of the work done. As a look at the San Francisco Chronicle's story about the original listing shows, the wonderful swimming pool and several thousand square feet have been added to the house. On the other hand, the the original listing from last January was for the house in a five-acre plot, while the latest listing is for 2.4 acres of land — no doubt that is the developer's real prize here. It'll be fascinating to see what happens next to this storied home.
The Crosby Estate is for sale at US$28.995 million — see more details and pictures.



Toby Keel is Country Life's Digital Director, and has been running the website and social media channels since 2016. A former sports journalist, he writes about property, cars, lifestyle, travel, nature.
