Bing Crosby’s Estate Sells for $25 Million

Bing Crosby's historic Hillsborough estate, built in 1929 and once serving as a Hollywood retreat for the legendary singer and his family, has sold for $25 million, $15 million below its original $40 million asking price. The French Chateau-style property covers over 14,000 to 16,600 square feet, includes 11 bedrooms, and features extensive historic renovations and antiques from William Randolph Hearst's collection. Originally commissioned by the family of Seabiscuit's owner, the estate remained in the Crosby family for more than 60 years. The sale follows the 2024 death of Crosby's second wife, Kathryn Crosby. A local Hillsborough buyer, dedicated to preserving the estate's legacy, acquired the property. The transaction is among the top five most expensive in Hillsborough's history.