Some homes have such fascinating stories that they become more than a piece of real estate – they become living chapters of history. The former California residence of legendary Hollywood crooner Bing Crosby is once again up for sale, and it is turning heads for good reason.
Nestled in the prestigious San Francisco suburb of Hillsborough, the sprawling French chateau-style estate is now listed at $29 million – offering a rare opportunity to own a piece of Old Hollywood grandeur.
A century of history
The story of this remarkable property long predates Crosby himself. As reported by Robb Report, the estate was originally designed by noted architects John Bakewell Jr. and Ernest Weihe for businessman Lindsay Howard, son of horse-racing enthusiast and Seabiscuit owner Charles Howard.
The original estate spanned 12 acres and included a king-size pool, hothouses, and the very stables that once housed champion racehorse Seabiscuit reports Redwood City Pulse.
When Bing Crosby and his second wife – actress Kathryn Grant – started their family in the late 1950s, they were eager to keep their children out of the Hollywood spotlight, eventually settling on this grand chateau-style home to raise their three children.
Crosby became the fifth owner of the home, and according to the Peninsula Time Tribune, owning the estate had been a dream of his for at least a decade – he bought it “without hesitation.”
The family made the home their own over the years, with Fox Business noting that much of the wood paneling and the staircase railing came from the collection of newspaper magnate William Randolph Hearst, a close friend of Bing’s, sourced from Europe and leftover from the construction of Hearst Castle.
Kathryn continued living in the home after Bing’s death in 1977, and his former office remains decorated with golf trophies and his Oscar for the 1944 film Going My Way. Following Kathryn’s passing in 2024 at age 90, the family listed the estate at $40 million.
As reported by Robb Report, it sold around three months later for a discounted $25 million to local real estate investor Mehrdad Elie, who undertook an extensive $3 million renovation that included replacing all carpeting with hardwood floors, refreshing the landscaping, and installing a new swimming pool. The property is now back on the market at $29 million.
Inside the $29 million estate: Old-world grandeur meets modern polish
The property is as extraordinary as one would expect a home of a Hollywood Legend from the golden era of the industry to be. According to Robb Report, the home offers 11 bedrooms, 10 full bathrooms, and five powder rooms across roughly 18,500 square feet spread over four levels. A grand entry foyer features a staircase with a 17th-century banister sourced from the collection of William Randolph Hearst.
Other highlights include a bar-equipped smoking room, an oval-shaped dining room with a Venetian glass chandelier, and walls painted in a floral motif by artist Albert Proom. A formal living room sports an ornate black-marble fireplace with French doors opening to lush grounds, a wood-paneled library lined with custom bookshelves, and a kitchen outfitted with a fancy Officine Gullo range.
The new owner also made structural changes to the footprint – Robb Report notes that Elie subdivided the formerly five-acre property into four separate lots, with the Crosby residence now sitting on a 2.4-acre parcel. The listing is held by Golden Gate Sotheby’s International Realty.
For anyone seeking a home that carries nearly a century of American cultural history within its walls, this Hillsborough estate may just be the most fascinating property on the San Francisco market today.