Echoes of Old Hollywood: Bing Crosby’s Former Home Lists at $40 Million

Nestled in the heart of Lower North Hillsborough, 1200 Jackling Dr is far more than a luxury estate—it is a chapter of California’s Golden Era preserved in stone, wood, and opulence. Listed for $40,000,000, this grand French chateau-style residence sprawls across 5.36 acres, offering unmatched privacy and provenance in one of the most exclusive neighborhoods in the Bay Area.

Built in 1929 by acclaimed architects John Bakewell Jr. and Ernest Weihe, the estate was once the beloved home of Hollywood legend Bing Crosby. It boasts an extraordinary architectural pedigree that transcends time. The property’s connection to the iconic racehorse Seabiscuit, whose stables once stood on the grounds, adds a unique historical flair rarely found in California real estate.

“This home isn’t just luxurious—it’s storied. The legacy of Bing Crosby and the estate’s ties to Seabiscuit create a sense of narrative that you simply can’t replicate,” said listing agent Jenn Gilson of Golden Gate Sotheby’s International Realty.

Where Historic Elegance Meets Modern Comfort

With over 18,500 square feet of living space spread across four levels, the residence features 11 bedrooms, 10 full bathrooms, and 5 half baths. Each detail was meticulously crafted to embody European sophistication—from Rococo plasterwork to intricate millwork and Georgian paneling. Many of the antique elements were personally selected by Crosby and sourced from the famed Hearst Collection, including hand-carved balustrades and fireplace mantels.

The estate offers multiple salons, a paneled library, and a grand formal dining room, each space designed for both intimate moments and large-scale entertaining. The private guest wing provides ultimate flexibility for multigenerational living or hosting high-profile guests in seclusion.

“It’s one of those rare properties where every room tells a story,” Gilson shared with Luxury Houses Magazine. “The combination of scale, beauty, and historical significance makes it a true legacy estate.”

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The Estate Grounds: A Sanctuary of Seclusion

Beyond its walls, 1200 Jackling Dr continues to impress. The grounds are a lush canvas of manicured gardens, shaded walking paths, and private courtyards. The multiple outdoor living areas are ideal for al fresco dining, wellness retreats, or even the restoration of equestrian facilities to honor the estate’s past.

The four contiguous parcels not only enhance privacy but also offer potential for future development—a rarity in Hillsborough real estate. From family estates to diplomatic retreats, the possibilities here are as vast as the acreage.

“This isn’t just a home—it’s a destination,” said Gilson. “Many clients see this as a sanctuary, a place where history and beauty merge in one of the most coveted corners of California real estate.”

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Living in Hillsborough: Prestige, Peace, and Proximity

Hillsborough, long known for its exclusivity and architectural significance, remains one of the most desirable zip codes in the state. Residents enjoy quick access to downtown San Francisco, SFO International Airport, and Silicon Valley, all while living in a quiet, tree-lined enclave with top-tier public and private schools.

The area is also rich in lifestyle amenities—think designer shopping in nearby Burlingame, award-winning restaurants, and private country clubs. This harmonious balance of accessibility and retreat is precisely why high-net-worth individuals and families continue to invest in Hillsborough real estate.

SEE MORE: Unparalleled Luxury: Guy Dreier-Designed Estate Lists for $7.5 Million in California

For buyers seeking to own a piece of California’s storied past while enjoying the finest luxuries of today, 1200 Jackling Dr offers a once-in-a-generation opportunity. This estate is not just on the market—it’s waiting for its next steward.

View the full listing on Zillow, For private tours and inquiries, visit Jenn Gilson at Golden Gate Sotheby’s International Realty.

* This property might not for sale at the moment you read this post; please check property status at the above Zillow or Agent website links*

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