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With hand-carved woodwork from three different 16th- and 17th-century European castles, a 4-ton stone fireplace imported from England, ceiling-to-floor frescoes and 11 bedrooms, this approximately 14,000-square-foot French chateau-style home in Hillsborough is not only notable for its grandeur, but also for its storied past. The 96-year-old estate includes a connection to a celebrity racehorse, two renowned San Francisco architects, a California newspaper mogul, and one of the world’s earliest multimedia icons.
Located on Jackling Drive in the Hillsborough Oakbridge neighborhood, the home is currently owned by the family of legendary entertainer Bing Crosby, who moved into the home with his wife, Kathryn Grant, in 1965 to reportedly raise their children away from the Hollywood spotlight. The estate has remained in the family ever since: After Crosby’s death in 1977, Grant continued living there until her death in 2024.
The family home is now on the market for the first time in 60 years with a potentially record-setting asking price of $40 million, according to listing agent Jennifer Gilson of Golden Gate Sotheby’s International Realty, who told Realtor.com that the city’s current $30-million record was set in 2021 with the sale of Space X founder and businessman Elon Musk‘s home.
Crosby’s ‘castle’
Originally built in 1929 for the Howard family, who gained fame for their champion race horse Seabiscuit, the 40-room estate has been called one of the finest examples of French architecture in America over the years, according to various news reports.
The four-level home spans 5.38 acres across four parcels and features 15 bathrooms,multiple salons and a separate guest wing, according to the sales listing. There’s also a paneled library, a smoking room with a built-in bar, a formal dining room with hand-painted murals by renowned post war artist Al Proom, as well as many imported European antiques hand-selected by Crosby and his wife, who renovated nearly every room in the house before moving in.
According to a Peninsula Times Tribune article published in 1966 at the time the Crosbys were moving into the home, the renovation work required 25 different subcontractors, six fulltime carpenters and one designer – Crosby’s former musical director John Scott Trotter who was also an amateur interior decorator.
The couple incorporated antiques from newspaper publisher and friend William Randolph Hearst‘s collection leftover from his California estate, Hearst Castle, including an entire hand-carved wooden staircase from an English abbey and 400-year-old wood paneling used in the living room. They also installed cornices, vintage oak moldings, a carved door and other bits and pieces from three different European castles throughout the home and imported a stone fireplace from England to place in the dining room. They also designed one room, named “Road to Morocco Hideaway,” specifically dedicated to Crosby’s film “Road to Morocco.” In the garden, they planted rows of the special hybrid “Crosby Rose.”
The ‘Seabiscuit’ era
Nearly 40 years before the property became Crosby’s home, property owner Lindsay Howard commissioned renowned San Francisco architects John Bakewell Jr. and Ernest Weihe, whose work includes San Francisco City Hall and the Hoover Library at Stanford University, to build the French chateau for his new wife. Originally, the estate spanned 12 acres and included a king-size pool, hot houses and the stables that later housed the race horse champion Seabiscuit. When the couple divorced in 1938, Charles Howard Sr., who gained fame as the owner of Seabisuit, bought the property from his son.
Crosby became the fifth owner of the home when he purchased it for $250,000 in the mid-1960s. He was no stranger to the estate: He shared a common interest in horses with the Howards, and had been a frequent guest at the home. According to the Peninsula Time Tribune, owning the estate had been a dream of his for at least a decade.
When the home came up for sale, Crosby bought it “”without hesitation,” the paper reported.
