The sprawling estate of Bing Crosby has hit the market for $40million after remaining in his family’s hands for more than half a century.
The magnificent, 13,635-square-foot French chateau-style residence, featuring a staggering 11 bedrooms and 15 bathrooms, is set to shatter the area’s previous record of $30million set by Elon Musk’s property sale in 2021.
Situated on 5.38 acres in one of California‘s most prestigious neighborhoods – Hillsborough – the home at 1200 Jackling Drive comes with a rich Hollywood history that dates back nearly a century.
Referred to as ‘The Bing Crosby Estate’, the home was originally built in 1929 and blends ‘timeless elegance with historic significance’, according to its listing.
The estate has a total 18,535 square feet, which includes both finished and unfinished areas, according to the floorplan artist.
‘This estate is truly one of a kind, blending Hollywood history, architectural grandeur, and Northern California prestige,’ said listing agent Jennifer Gilson of Sotheby’s International Realty.
‘A property of this significance rarely comes to market, making it an extraordinary opportunity for the next owner.’
By the time Crosby moved into the estate in 1965, he was already setting records across album sales, radio ratings and movies.
The sprawling estate of America’s ‘first multimedia star’ Bing Crosby has hit the market for a jaw-dropping $40million after remaining in the family’s hands for more than half a century
The magnificent 13,635-square-foot French chateau-style residence, featuring a staggering 11 bedrooms and 15 bathrooms, is set to shatter the area’s previous record of $30million set by Elon Musk’s property sale in 2021
By the time Crosby moved into the estate in 1965, he was already setting records across album sales, radio ratings and movies
The singer and actor made more than 70 films and more than 1,600 recorded songs – which turned him into a global icon.
He was most known for classics like ‘White Christmas’ and ‘Road’ movies with Bob Hope.
Crosby lived in the home with his wife, Kathryn, and their three children: Harry Lillis Jr., Nathaniel, and Mary Frances.
The couple made major renovations to the property. They added unique antique furniture and wood paneling from the collection of William Randolph Hearst, who was a close friend of Bing’s,’ as reported by SFGATE.
They also incorporated ‘a hand-carved wooden staircase banister and Georgian paneling from a 17th-century English manor home’, according to the Sotheby’s listing.
Kathryn Crosby also commissioned renowned San Francisco artist Al Proom to decorate the dining room walls.
Today, Bing’s custom dressing room has largely remained in tact, as does the library with its fireplace, built-in bookcase, and paintings of desert landscapes.
Situated on 5.38 acres in one of California’s most prestigious neighborhoods, the home at 1200 Jackling Drive comes with a rich Hollywood history that dates back nearly a century
Referred to as ‘The Bing Crosby Estate,’ the home was originally built in 1929 and blends ‘timeless elegance with historic significance,’ according to its listing
Crosby lived in the home with his wife, Kathryn, and their three children: Harry Lillis Jr., Nathaniel, and Mary Frances
Kathryn commissioned renowned San Francisco artist Al Proom to decorate the dining room walls
The estate has a total 18,535 square feet, which includes both finished and unfinished areas, according to the floorplan artist
The couple made major renovations to the property. They added unique antique furniture and wood paneling from the collection of William Randolph Hearst, who was a close friend of Bing’s,’ reported SFGate
Crosby met his future wife when she interviewed him for a column in her hometown newspaper. The couple married in 1957 – she was just 23, while he was 54.
Following Kathryn’s death in 2024 at age 90, the couple’s children decided to begin a new chapter by listing the family home.
‘This isn’t just a home; it’s a landmark of California’s golden era,’ Gilson emphasized.
‘The estate’s French chateau-inspired architecture, its ties to icons like Bing Crosby, and its connection to the legendary Seabiscuit create a rich history that few properties can claim.’
‘Nestled on over five acres in one of Hillsborough’s most prestigious enclaves, it embodies a level of elegance and privacy that is nearly impossible to replicate today,’ she continued. ‘This is a legacy estate, steeped in sophistication and timeless appeal.
Before Crosby, the property’s story began in the early 1920s when Lindsay Howard, son of a Buick distributor and owner of a Burlingame Buick dealership, commissioned the home as a wedding gift for his new bride, Anita Zabala of Salinas, daughter of a prominent Spanish family, SFGATE reported.
Howard hired San Francisco’s most celebrated architects – John Bakewell Jr. and Ernest Weihe – to design the couple’s dream home on 12 acres of prime Hillsborough land.
The architects were renowned for their work.
They also incorporated ‘a hand-carved wooden staircase banister and Georgian paneling from a 17th-century English manor home,’ according to the Sotheby’s listing
Bing Crosby first visited the home when it belonged to Lindsay Howard when he ‘fell in love’ with the property
After Charles Howard’s death, the property changed hands twice before Crosby finally had the opportunity to purchase his dream home in the early 1960s
Bakewell, who studied at UC Berkeley under Bernard Maybeck, went on to create some of the Bay Area’s most iconic buildings, including San Francisco City Hall, Temple Emanu-El, and Stanford’s Hoover Library.
Weihe’s impressive work included the San Francisco Hall of Justice and the Morrison Planetarium at the California Academy of Sciences.
Their masterpiece featured soaring ceilings, exquisite frescos, hand-painted wallpaper, intricate hand-carved woodwork, and elaborate fireplaces throughout.
Now, nearly 100 years later, many of these original elements remain perfectly preserved, including the formal dining room’s Venetian-glass chandelier that casts a golden glow over the floral-patterned walls and the original ‘smoking room’ with its built-in bar.
The Howard marriage eventually ended with divorce.
Anita ended up dating sugar magnate Adolph Spreckels Jr. before marrying into American royalty as the wife of George Vanderbilt, while Lindsay’s father, Charles Howard, acquired the estate.
Charles Howard, a passionate horse racing enthusiast, added his own touch and style to the property.
Today, Bing’s custom dressing room has largely remained in tact, as does the library with its fireplace, built-in bookcase, and ‘paintings of desert landscapes
This includes its library with its fireplace, built-in bookcase and paintings of desert landscapes
He made extensive use of the property’s stables and was the owner of legendary racehorse Seabiscuit.
Bing Crosby first visited the home when it belonged to Lindsay Howard when he ‘fell in love’ with the property.
The two men were friends and partners in a successful racetrack and stables enterprise, and Crosby reportedly ‘fell in love with the Hillsborough estate’ at that time.
After Charles Howard’s death, the property changed hands twice before Crosby finally had the opportunity to purchase his dream home in the early 1960s.
At $40million, the listing would easily surpass the current Hillsborough record set when Elon Musk sold his property for $30million in 2021.
The Tesla and SpaceX CEO sold his Silicon Valley estate for $7.5million less than the original $37.5million asking price when it was first listed in June of that year.
He struggled to sell the home, listing it three times before finding a buyer.
The world’s second richest man sold it after he fulfilled his pledge to ‘own no home.’
Elon Musk sold his Silicon Valley estate for $30million, the last of his seven California homes, and moved to Texas. This 109-year-old European style home sits on 47 acres of land south of San Francisco
Musk, 53, who has a net worth of $347.7billion, had previously shared that the 47-acre property south of San Francisco was his ‘last remaining house.’
‘My primary home is literally a ~$50k house in Boca Chica / Starbase that I rent from SpaceX. It’s kinda awesome though,’ Musk tweeted at the time.
The 16,000-square-foot estate features seven bedrooms, seven bathrooms, a music room, grand ballroom and a cocktail room with retractable library shelves.
