After Bing Crosby’s first wife, Dixie Lee, died in the early 1950s, the beloved entertainer met a young actress named Kathryn Grant on a Paramount lot and married her in 1957. The couple soon packed up and left their Los Angeles home in the Holmby Hills neighborhood and the Hollywood spotlight behind, ultimately settling down with their three children at a majestic French-style chateau in the affluent and family-friendly San Francisco suburb of Hillsborough.

“Hillsborough was like a little town,” Kathryn told the SFGate in a 2001 interview. “In Holmby Hills, there were no young people—it was an area that grew old. We never could have friends over unless we hauled them in. In Hillsborough, kids were coming over the back fence all the time. We could take the bikes to the schoolyard to play on the jungle gym, and the public schools were fabulous, the churches were fabulous. It was a normal upbringing.”

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The late actor and crooner reportedly paid $175,000 in the 1960s for the property and lived there until he died in 1977. Kathryn passed away in 2024 at age 90, and the family listed the estate early the next year for a record-setting $40 million. It sold around three months later for a discounted $25 million to local real estate investor Mehrdad Elie, who quickly undertook an extensive $3 million renovation that included replacing all the carpeting with hardwood floors, refreshing the landscaping, and installing a new swimming pool.

Elie also subdivided the formerly five-acre property into four separate lots, with the Crosby residence now sitting on a smaller 2.4-acre parcel, and even had the 1200 Jackling Drive address changed in honor of Kathryn, who had always envisioned it as 1200 Armsby Drive. Now, less than a year later, the place has returned to the market for a dash under $29 million, with Jennifer Gilson of Golden Gate Sotheby’s International Realty holding the listing.

Designed almost a century ago by noted architects John Bakewell Jr. and Ernest Weihe for businessman Lindsay Howard, the son of horse-racing enthusiast and Seabiscuit owner Charles Howard, and his wife Anita, the whitewashed brick structure was previously renovated during Crosby’s tenure and featured as a Decorators’ Show House in 1998.

Many of the original details remain in the 11-bedroom, 15-bathroom abode, which features roughly 18,500 square feet of finished and unfinished living space across four levels, including antiques from the collection of newspaper publisher and Crosby friend William Randolph Hearst—a 17th-century wood staircase banister, linen fold paneling, and custom furnishings among them.

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Other highlights include a bar-equipped smoking room and 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 marble fireplace and French doors spilling out to the lush grounds; a handsome wood-paneled library is lined with custom bookshelves; and the kitchen is outfitted with a fancy Officine Gullo range. There’s also an upstairs primary suite with dual closets and baths, as well as a separate guest wing.

In addition to his primary residence, the “White Christmas” singer owned a Palm Desert retreat that has been touted as the site of an alleged tryst between President John F. Kennedy and Marilyn Monroe in the 1960s; it last went up for sale in late 2024 for $13.5 million and has since been removed from the market. He also had a Nevada ranch in Elko and a home in L.A.’s Toluca Lake neighborhood. 

Click here for more photos of the Hillsborough residence.