Bing Crosby's Historic Bay Area Estate Hits the Market for $40 Million.
A stunning French-style chateau from the 1920s, once owned by the late star Bing Crosby, is hitting the market in Hillsborough, a posh suburb of San Francisco, for the first time in nearly 60 years.
If you've ever fantasized about owning a gorgeous chateau in the desirable Bay Area, now's your chance! This beautiful estate, spanning over five acres and previously owned by the legendary actor and singer, is up for grabs at a price of $40 million. Crosby and his second wife, Kathryn, who sadly passed away last year at 90, bought the property back in the 1960s for just $175,000.

Credit - Jason Wells/Golden Gate Creative
The home features 11 bedrooms and 15 bathrooms, with nearly 14,000 square feet of living space filled with antiques from Crosby's friend, newspaper mogul William Randolph Hearst. Highlights include a stunning 17th-century wooden staircase banister, intricate linen fold paneling, and custom furnishings.
This stunning property was originally crafted nearly a century ago by renowned architects John Bakewell Jr. and Ernest Weihe for Lindsay Howard, the son of horse-racing aficionado and Seabiscuit owner Charles Howard, along with his wife Anita. The whitewashed brick building underwent significant renovations during Crosby’s time and was showcased as a Decorators’ Show House in 1998.

Credit - Jason Wells/Golden Gate Creative
One of the highlights is a smoking room complete with a bar, and the oval dining room features a beautiful Venetian glass chandelier, floral-patterned walls, and French doors that open up to the lush grounds.
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Other impressive features include a formal living room with an intricately designed fireplace, a grand piano that appeared in the film High Society, and access to a covered terrace. There's also a stylish wood-paneled library with its own fireplace and built-in shelves. The kitchen boasts a vintage walk-in refrigerator and connects to a pantry, prep area, breakfast nook, and mudroom. Upstairs, the primary suite offers dual closets and bathrooms, plus there are separate quarters for staff.

Credit - Jason Wells/Golden Gate Creative
Harry, the couple's son and an investment banker based in New York, shared that he and his siblings, Nathaniel and Mary Frances, have decided to put their family home on the market following their mother's recent passing, as reported by The Wall Street Journal. He mentioned, “It’s difficult to turn the page emotionally,” he added, “but all good things come to an end.”

Credit - Jason Wells/Golden Gate Creative
The property is listed at an asking price of $40 million, which could set a record for the San Mateo County area if it sells close to that amount. The listing is managed by Jennifer Gilson from Golden Gate Sotheby’s International Realty. The highest sale so far was in 2021 when a home owned by billionaire Elon Musk sold for $30 million.
