American singer Bing Crosby moved to Hillsborough, California, with his second wife, Kathryn, and their three children in 1964, after selling their home in Holmby Hills, Los Angeles.
Their first home in the area was at 101 Robin Road in Hillsborough’s Carolands neighborhood, but they moved by the end of 1965 to a larger property on Jackling Drive at Armsby Drive in Hillsborough Oaksbridge.
The 1925 whitewashed brick home, built in the style of a French chateau, was referred to locally as the Crosby Estate and remained Bing Crosby’s main home until his death in 1977. The home was the setting for several Minute Maid orange juice commercials featuring the Crosby family in the 1960s and 70s.