Bing Crosby’s Historic Hillsborough Estate Hits the Market for $40M

Casey Sternsmith

If you’ve ever dreamed of owning a piece of Hollywood history nestled in the serene elegance of San Mateo County, the opportunity has arrived. 🎬🏡 The legendary Bing Crosby estate at 1200 Jackling Drive in Hillsborough is now on the market for $40 million, and it's nothing short of extraordinary.

As long-time residents and real estate experts in the Hillsborough area, the Sternsmith Group is excited to spotlight this one-of-a-kind listing. Not only does this property offer stunning architecture and luxurious amenities, but it also carries a deep legacy tied to one of the most iconic voices in American music history. 🏰📍✨


A Star-Studded Legacy 🌟🎶🏡

Built in 1929, this grand French chateau-style mansion was purchased by Bing Crosby and his wife, Kathryn Grant, in the 1960s. They raised their three children here, and the home remained in the Crosby family until this year. Following Kathryn’s passing in 2024, the estate is now being offered by their son, Harry Crosby.

From the grand staircase sourced from William Randolph Hearst’s collection to the richly carved fireplace in Bing’s study and a dazzling Venetian chandelier in the dining room—this home is a museum of elegance and history.


Estate Features & Highlights 🛋️🌲✨

  • 14,000 square feet of interior space

  • 11 bedrooms and 15 bathrooms

  • Over 5 acres of landscaped grounds

  • One-of-a-kind architectural and design elements

  • Prime location in one of Hillsborough’s most exclusive neighborhoods

It’s the ultimate blend of Hollywood grandeur and Northern California prestige.


This exquisite listing is presented by Jennifer Gilson of Sotheby’s International Realty, whose exceptional work has brought renewed attention to this historic gem. Her thoughtful marketing highlights both the property’s legacy and its modern-day elegance. 👏🏡📸


If making this property your home is a dream come true, call us today at 650-678-5455.

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Insightful local knowledge and extensive expertise. We looks forward to earning your family’s trust and leveraging our success for your benefit for generations to come. We looks forward to earning your family’s trust and leveraging our success for your benefit for generations to come.

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