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Bing Crosby estate in Hillsborough seeks $40M

14K sf mansion on 5 acres on the market for first time in 60 years

<p>A photo illustration of Bing and Katherine Crosby along with 1200 Jackling Drive in Hillsborough (Getty, Sotheby&#8217;s International Real Estate)</p>

A photo illustration of Bing and Katherine Crosby along with 1200 Jackling Drive in Hillsborough (Getty, Sotheby’s International Real Estate)

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Key Points

AI Generated.
This summary is reviewed by TRD Staff.

  • The Bing Crosby estate in Hillsborough, California, has been listed for $40 million.
  • The 13,600-square-foot mansion sits on 5 acres and was built in 1929.
  • The estate was purchased by Bing Crosby in the early 1960s and includes 11 bedrooms and 15 bathrooms.

The family of the late Bing Crosby has listed his 1920s Hillsborough mansion for $40 million.

The death of Der Bingle’s wife Katherine last fall has led their son Harry to put the 13,600-square-foot estate up for sale after nearly 60 years at 1200 Jackling Drive, the San Francisco Chronicle reported

Bing Crosby, the Academy Award-winning actor and crooner known for such hits as “White Christmas” died in 1977. He was 74. His wife died in September at 90.

“It’s difficult to turn the page emotionally, but all good things come to an end,” Harry told the Wall Street Journal. 

Their 11-bedroom, 15-bathroom French chateau-style mansion, built in 1929, sits on 5.4 acres within the unincorporated town in San Mateo County. A $40 million sale would break a local record held by Tesla founder Elon Musk, who sold a Hillsborough home in 2021 for $30 million. 

In the early 1960s, Bing Crosby bought the estate as a surprise for his second wife, Kathryn, for $175,000.

The Crosbys moved in with their two kids in December 1965, according to the listing, then conducted extensive renovations, incorporating antiques from William Randolph Hearst’s collection, including a hand-carved wooden staircase banister and Georgian paneling from a 17th-century English manor home.

The dusky brick chateau, with a crimson front door and iron balcony overhead, is of another time and place.

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The mansion has a smoking room with a built-in bar, a grand piano featured in the 1956 film “High Society,” a Venetian glass chandelier, hand-painted rose detailing on the walls and a wood-paneled library.

“This estate is truly one of a kind, blending Hollywood history, architectural grandeur, and Northern California prestige,” Jennifer Gilson, who holds the listing through Golden Gate Sotheby’s International Realty, told the Chronicle.

“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.”

The century-old mansion was designed by architects John Bakewell Jr. and Ernest Weihe, known for their work on San Francisco City Hall, for businessman Lindsay Howard, the son of Seabiscuit owner Charles Howard.

In 1998, the home was opened to the public for the first time since Crosby’s death when it was featured as a Decorators’ Show House. 

Crosby, among the world’s first multimedia stars, made more than 70 feature films and 1,600 songs over the course of his career.

Dana Bartholomew

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