Bay Area Estate once home to legendary Hollywood icon being sold for $40M

HILLSBOROUGH, Calif. - A piece of Hollywood’s golden age is up for sale on the Peninsula, offering a rare opportunity to own the home of the late legendary singer-actor Bing Crosby.

What we know:

The expansive five-acre property, in the exclusive community of Hillsborough, is being sold for $40 million.

Located at 1200 Jackling Drive, the sale of the property could set a record in Hillsborough, listing agent Jennifer Gilson of Golden Gate Sotheby’s International Realty confirmed. 

It's the first time the property, which has remained in the Crosby family, will be on the market in more than 60 years, according to the realtor.

‘Extraordinary’ opportunity

What they're saying:

"This estate is truly one of a kind, blending Hollywood history, architectural grandeur, and Northern California prestige," Gilson told KTVU in an email, adding, "A property of this significance rarely comes to market, making it an extraordinary opportunity for the next owner." 

The nearly 14,000-square-foot French chateau-style mansion has 11 bedrooms, 10 full bathrooms, and five half bathrooms.

It was built in 1929. 

The backstory:

The home is steeped in history. It was originally commissioned by Lindsay Howard, the son of horse-racing entrepreneur Charles Howard, best known for his champion thoroughbred horse Seabiscuit. 

Acclaimed San Francisco City Hall architects John Bakewell Jr. and Ernest Weihe designed the estate. 

Crosby, a horse-racing enthusiast himself, purchased the property in the early 1960s, as a surprise for his wife, Kathryn, according to Gilson. 

The Crosbys and their three children moved in December 1965, and the couple remodeled the home to further enhance its grandeur, the realtor said. 

Among the renovations, the Crosbys added antiques from the collection of newspaper magnate William Randolph Hearst, including a 17th-century hand-carved wooden staircase banister and Georgian paneling from an English manor home, the property listing noted. 

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With its carefully preserved craftsmanship and architectural details, the Bing Crosby Estate is being described as a landmark and "a true icon of elegance and history."

Gilson said the feedback and interest have been great so far, especially given the sprawling property's proximity to the downtown area.

On Wednesday, she said the property was set to launch on the market this week.

"Nestled on over five acres in one of Hillsborough’s most prestigious enclaves, it embodies a level of elegance and privacy that is nearly impossible to replicate today," Gilson said. "This is a legacy estate, steeped in sophistication and timeless appeal."

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