Bing Crosby's Hillsborough Estate Sells for Record $25 Million
Bing Crosby's Estate Achieves Landmark Sale
In an unprecedented real estate transaction, the Bing Crosby Estate located at 1200 Jackling Drive in Hillsborough has officially changed hands for an astounding $25 million. This sale, which occurred on June 17, 2025, marks a significant milestone as the highest sale recorded in the area in the last two years. Known as one of the San Francisco Bay Area's most affluent communities, Hillsborough has seen its fair share of luxurious properties, but none as iconic as this one.
The estate's listing was handled by the renowned Jenn Gilson of Golden Gate Sotheby's International Realty. Gilson's exceptional marketing strategy brought the property to a global audience, capturing the attention of media outlets such as The Wall Street Journal, Robb Report, and People Magazine. This was the first time in 60 years that the estate was available on the market, making it a coveted treasure for affluent buyers.
Bing Crosby, the legendary American singer and actor, purchased the property in the 1960s for only $175,000. The estate showcases a French-style chateau that boasts nearly 14,000 square feet of lavish living space, featuring 11 bedrooms and 15 bathrooms. Decorated with antiques and furnishings from Crosby’s friend William Randolph Hearst’s collection, the home’s interiors offer a glimpse into the grandeur of its past, highlighted by a stunning 17th-century wood staircase and custom linen fold paneling.
Gilson expressed her pride in representing the Crosby family during this significant sale, stating, "It is an honor and privilege to have represented the Crosby family in the sale of this iconic property. Preparing a home of this stature and bringing it to market is our specialty. We thoroughly understood the need to expose such a unique offering to possible affluent buyers, whether they were mere minutes down the street or halfway across the globe."
Ultimately, the estate found a new owner—a local Hillsborough resident drawn to the property’s exquisite architecture and rich history. Gilson has been a driving force in the local real estate market, recently earning a spot on the 2025 Real Trends Verified list, ranking her among the top 250 individual agents nationally by sales volume.
This historic sale not only pays homage to Bing Crosby's legacy but also highlights the vibrancy and allure of the Hillsborough luxury real estate market. As Gilson continues to lead significant transactions in Hillsborough, Burlingame, and the broader Silicon Valley area, potential buyers are always on the lookout to uncover their next dream estate in this prestigious enclave.
For more information about the sale or to inquire about luxury real estate in the Bay Area, interested parties are encouraged to reach out to Jenn Gilson by phone or email, as she remains a trusted resource in this elite market.