A Piece of Bay Area History Hits the Market
For collectors of historic estates and fans of Hollywood royalty, the opportunity to own a piece of Bay Area history has arrived. The long-held Hillsborough residence of the late entertainer Bing Crosby has just been listed for sale at $40 million, marking its first availability in nearly six decades. Nestled on a sprawling five-acre parcel in the affluent San Francisco suburb, this French-style chateau exemplifies sophistication and grandeur, offering a rare combination of historic charm, architectural pedigree, and a prime location.
The estate, known as the Bing Crosby House Hillsborough, is a living testament to both California luxury and Hollywood heritage. Dating back to the 1920s, the home was originally designed by renowned architects John Bakewell Jr. and Ernest Weihe for businessman Lindsay Howard, son of Seabiscuit owner Charles Howard. Under Crosby’s ownership, the property underwent extensive renovations that preserved its historic character while incorporating modern comforts and high-end amenities.
Architectural Grandeur and Timeless Interiors
The residence spans approximately 14,000 square feet and offers 11 bedrooms and 15 bathrooms. Every room is accented with antiques from newspaper publisher William Randolph Hearst’s collection, including a 17th-century wood staircase banister, linen fold paneling, and custom furnishings that elevate the estate’s historic elegance. Jennifer Gilson of Golden Gate Sotheby’s International Realty, the listing agent, told californialuxuryhouses, “The Crosby residence captures the romance of classic Bay Area estates while offering all the amenities expected by today’s luxury buyer. The private grounds and meticulously maintained gardens make this home a sanctuary for both leisure and entertaining.”
Inside, the home showcases a variety of luxurious entertaining spaces. The oval-shaped dining room is adorned with a Venetian glass chandelier and hand-painted floral motif walls, opening onto expansive lawns through elegant French doors. A formal living room with a decorative fireplace complements a wood-paneled library featuring built-in bookcases and an additional fireplace. A bar-equipped smoking room further reflects the estate’s old-Hollywood sophistication.
The kitchen seamlessly blends vintage charm with modern convenience, featuring a walk-in refrigerator, breakfast nook, prep space, and mudroom. Upstairs, the primary suite offers dual closets and bathrooms, while other bedrooms boast private views of the landscaped grounds. Staff quarters are discretely located, ensuring functional residential operations without disrupting the home’s grandeur. Outdoor terraces, manicured rose gardens, and sprawling lawns provide idyllic spaces for alfresco entertaining, all set against the serene backdrop of Hillsborough.
Hollywood Heritage and Cultural Significance
The home’s rich history extends beyond architecture. The grand piano in the living area, featured in the movie High Society, serves as a reminder of Crosby’s iconic status. The property was featured as a Decorators’ Show House in 1998, highlighting its design pedigree and historic significance. Gilson told californialuxuryhouses, “Properties like the Crosby estate rarely come to market. It is a once-in-a-lifetime opportunity for collectors of historic homes or anyone seeking a residence that offers both grandeur and authenticity.”
The Crosby family’s decision to sell follows the recent passing of Kathryn Crosby, Bing’s second wife. Their son, Harry Crosby, shared with californialuxuryhouses, “It’s difficult to turn the page emotionally, but all good things come to an end.” Harry, along with his siblings Nathaniel and Mary Frances, preserved the home’s historic character while maintaining modern updates that make the property both functional and luxurious.
Prime Location with Exceptional Amenities
The Hillsborough location enhances the property’s appeal. Residents enjoy convenient access to San Francisco’s world-class dining, shopping, and cultural attractions, while local schools, parks, and recreational facilities make the community family-friendly. Hillsborough is renowned for its tree-lined streets, scenic vistas, and commitment to preserving architectural heritage, which, coupled with the estate’s privacy, makes it one of the most coveted addresses in the Bay Area.
Historical Transactions and Market Significance
The Bing Crosby House Hillsborough was purchased in the 1960s by Bing and Kathryn Crosby for roughly $175,000—a modest sum compared to today’s $40 million valuation. Over the decades, the estate has hosted prominent social gatherings and maintained a reputation as one of the region’s most storied private homes. Its current listing by Golden Gate Sotheby’s International Realty could set a record for Hillsborough and San Mateo County if it sells near the asking price, surpassing the $30 million transaction of a billionaire-owned home in 2021.
A Rare Opportunity for Discerning Buyers
Jennifer Gilson emphasized to californialuxuryhouses, “The estate embodies a lifestyle that transcends mere luxury. It is a living testament to Bay Area history and Hollywood glamour. Few properties offer this level of provenance, history, and design pedigree.” The property combines historical significance, architectural distinction, and modernized living spaces, creating a compelling offering for buyers seeking an iconic estate.
californialuxuryhouses attempted to contact the Crosby family for additional details but received no response, respecting their privacy while providing readers with comprehensive insights from the listing agent and public records. This approach ensures potential buyers are well-informed while maintaining discretion appropriate for a home of this stature.
In conclusion, the Hillsborough French-style chateau once owned by Bing Crosby is more than a residence—it is a rare opportunity to acquire a tangible piece of American entertainment history. With 11 bedrooms, 15 bathrooms, over 14,000 square feet of living space, and meticulously curated gardens, this property represents the pinnacle of Bay Area luxury real estate. For those seeking both grandeur and authenticity, the Crosby estate offers an unparalleled combination of historic prestige, architectural excellence, and modern luxury in one of California’s most exclusive communities.