Historical Homes
1200 Jackling Drive, Hillsborough, California
Architects: John Bakewell Jr. & Ernest Weihe
Year Built: 1929
Set on a grand 5.38-acre estate in prestigious Lower North Hillsborough, this opulent French chateau-style residence is a rare architectural treasure. Completed in 1929 and originally commissioned by Lindsay Howard as a wedding gift, the estate was designed by the acclaimed architectural duo John Bakewell Jr. and Ernest Weihe, best known for designing San Francisco City Hall.
In the early 1960s, the estate became famously associated with entertainer Bing Crosby, who purchased the property as a surprise for his wife Kathryn Crosby. The family—including children Harry Lillis Jr., Nathaniel, and Mary Frances—moved in just before Christmas in 1965.
Soon after, the Crosbys began a remarkable renovation project. Kathryn incorporated a selection of antiques from William Randolph Hearst’s private collection, including a hand-carved wooden staircase banister and Georgian paneling originally from a 17th-century English manor house. To further elevate the home’s aesthetic, Kathryn commissioned noted San Francisco artist Al Proom to decorate the dining room walls, adding a unique layer of cultural and artistic value.
The residence spans over 13,600 square feet and features 11 bedrooms, 10 full bathrooms, and 5 half bathrooms. Inside, it boasts soaring ceilings, richly detailed millwork, and the refined elegance of authentic 1920s French revival design. Despite its vast size and lavish appointments, the home maintains a warmth and intimacy that reflect its storied past.
Today, the Bing Crosby Estate stands not only as a piece of architectural excellence but also as a living legacy to one of America’s most beloved entertainers and his family. It remains one of Hillsborough’s most iconic properties, treasured for both its history and enduring sophistication.
Photography Credit: Golden Gate Sotheby’s International Realty
