Bing Crosby’s Legendary Hillsborough Estate, Rooted in California’s Golden Era, Lists for $28.995 Million

Originally designed by renowned architects John Bakewell Jr. and Ernest Weihe, the French château estate has welcomed Hollywood royalty, housed Seabiscuit’s owner, and preserved nearly a century of California history on one of Hillsborough’s largest private estates.

Some homes are measured by square footage.

Others are measured by the stories they carry.

The estate known today as 1200 Armsby Drive belongs firmly in the latter category. Hidden behind mature trees in the prestigious Lower North Hillsborough neighborhood, the French château-style residence has witnessed nearly a century of California history—from the golden age of Hollywood to the legendary career of Seabiscuit and the evolution of Silicon Valley just beyond its gates.

Now offered for $28.995 million, the property spans more than 2.4 private acres, making it one of the largest residential estates currently available on the San Francisco Peninsula. Yet its true significance extends far beyond its acreage.

Originally designed in 1925 by celebrated architects John Bakewell Jr. and Ernest Weihe, the residence remains one of the Bay Area’s finest surviving examples of French Renaissance Revival architecture.

“This is not simply another luxury estate,” said Jenn Gilson of Golden Gate Sotheby’s International Realty. “It’s one of Hillsborough’s defining landmark residences—a property where architectural significance and California history intersect in an extraordinary way.”

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A French Château Inspired by Europe’s Great Estates

Bakewell and Weihe were already among California’s most respected architects when they conceived the residence.

Drawing inspiration from Champ Soleil in Newport, Rhode Island, and La Lanterne at Versailles, the architects created a château that embraced European symmetry, monumental proportions, and classical craftsmanship while remaining perfectly suited to California’s climate.

Nearly one hundred years later, those architectural decisions continue to define the estate.

The dramatic reception hall welcomes visitors beneath soaring ceilings before revealing finely detailed wall paneling, handcrafted wood floors, and one of the home’s most remarkable historic elements—a carved staircase banister acquired from the collection of publishing magnate William Randolph Hearst, believed to date to seventeenth-century England.

Throughout the residence, imported materials and handcrafted details reinforce the sense that every room was created not merely as living space but as architecture intended to endure for generations.

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Rooms That Tell Their Own Stories

Unlike many historic estates where grandeur overwhelms comfort, the Crosby Estate achieves a remarkable balance.

The formal living room centers around a striking marble fireplace while generous windows overlook the estate’s park-like grounds.

Nearby, an extraordinary wood-paneled library showcases another Hearst Collection acquisition: richly carved paneling surrounding a dramatic black marble fireplace.

Perhaps the home’s most memorable entertaining space is the oval dining room.

Anchored by an elegant Venetian chandelier, the room is further distinguished by hand-painted rose garden murals created by noted artist Albert Proom, transforming formal dinners into occasions framed by genuine works of art.

Adjacent smoking and bar rooms preserve the gracious entertaining traditions of California’s Golden Era while remaining surprisingly intimate in scale.

“The craftsmanship throughout the residence simply doesn’t exist in modern construction,” Gilson said. “Every room reflects a level of artistry that would be extraordinarily difficult to recreate today.”

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The Estate That Helped Shape American Racing History

Long before Bing Crosby arrived, another legendary American name called the estate home.

The residence was originally commissioned by Lindsay C. Howard, whose father Charles Howard would become one of the most influential figures in Thoroughbred racing after purchasing the property in 1938.

Charles Howard is remembered today as the owner of Seabiscuit, the undersized racehorse whose unlikely victories captured the imagination of Depression-era America.

Between 1938 and 1940, Seabiscuit lived on the Hillsborough estate, where extensive horse facilities, riding tracks, barns, and pastureland occupied much of what are now manicured gardens.

Although urban legends long claimed the famous horse was buried on the property, Seabiscuit’s final resting place is actually Ridgewood Ranch in Mendocino County.

Still, the estate remains inseparable from one of the greatest stories in American sporting history.

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Bing Crosby’s Private Retreat

Perhaps no owner became more closely associated with the property than Harry “Bing” Crosby.

Purchased in 1965 by Bing and Kathryn Crosby, the estate remained the family’s home for nearly six decades.

Following Bing’s passing in 1977, Kathryn Crosby continued living at Armsby Drive until 2024, making the property one of the longest-held celebrity residences in Northern California.

During their ownership, the Crosbys introduced carefully selected historic architectural elements while preserving the home’s French-inspired elegance.

Music frequently filled the grand salons as family and friends gathered for evenings that reflected Bing Crosby’s relaxed hospitality.

The residence also became familiar to television audiences through the family’s Minute Maid orange juice commercials filmed on the estate during the 1960s.

“This home wasn’t simply owned by Bing Crosby,” explained Pierre Buljan of Compass. “It was truly the Crosby family’s home for generations, and that legacy remains woven into every corner of the property.”

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A Historic Estate Adapted for Modern Living

While history defines the residence, thoughtful modernization ensures it functions effortlessly for contemporary lifestyles.

The estate encompasses approximately 13,635 square feet of finished living space, expanding to more than 18,500 square feet across four levels.

Eleven bedrooms and fifteen bathrooms provide exceptional flexibility for multigenerational living, staff accommodations, or long-term guests.

The gourmet kitchen has been updated to contemporary standards while remaining architecturally sympathetic to the original residence.

Nearby, breakfast rooms, service spaces, executive offices, and generous informal gathering areas create a floor plan that feels remarkably current despite the home’s historic origins.

“The current owner approached every improvement with tremendous respect for the architecture,” Buljan said. “The result is a home that feels authentic rather than renovated.”

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Grounds Designed for Privacy and Possibility

Estate-scale land has become one of Hillsborough’s rarest luxuries.

Spread across more than 2.4 acres, the Crosby Estate retains much of the openness that once accommodated horse paddocks and riding facilities.

Today, sweeping lawns surround a resort-style swimming pool and spa, while mature specimen trees create extraordinary privacy rarely encountered this close to San Francisco and Silicon Valley.

Walking paths weave through carefully maintained gardens before connecting to terraces positioned for outdoor entertaining.

The generous acreage also provides flexibility for future enhancements while preserving the estate’s historic character.

Readers interested in the broader Peninsula market can also explore our California Luxury Real Estate Market Guide, while our features on Largest Homes in California and Architecture Styles of Luxury Homes in California provide additional context on the state’s most significant estates.

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A Legacy That Cannot Be Recreated

Unlike contemporary luxury homes where value is often measured by amenities alone, the Crosby Estate offers something increasingly impossible to acquire.

Architecture by two celebrated California architects.

A direct connection to one of Hollywood’s greatest entertainers.

An important chapter in American horse racing history.

Historic craftsmanship incorporating artifacts from the Hearst Collection.

And one of Hillsborough’s largest surviving estate parcels.

Taken together, they create a residence whose significance extends well beyond luxury real estate.

“This is a once-in-a-generation opportunity,” Gilson said. “Homes like this are part of California’s cultural history. They’re not simply purchased—they’re entrusted to the next steward.”

Prospective buyers can view additional photography, historical documentation, floor plans, pricing history, and current listing details on Zillow.

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Property Overview

• Address: 1200 Armsby Drive, Hillsborough, California 94010
• Price: $28,995,000
• Living Area: 18,535 sq ft (approximately 13,635 sq ft finished)
• Lot Size: 2.44 acres
• Bedrooms: 11
• Bathrooms: 10 Full | 5 Half
• Year Built: Originally designed in 1925; completed in 1930
• Architects: John Bakewell Jr. & Ernest Weihe

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Listing Representation

The Crosby Estate is represented by Jenn Gilson of Golden Gate Sotheby’s International Realty together with Pierre & Alex Buljan of Compass.

For additional information or to arrange a private showing, prospective buyers may contact Jenn Gilson at (650) 642-6957 or Pierre & Alex Buljan at (650) 400-1188.