Legendary entertainer Bing Crosby was one of America’s most beloved singers and actors, renowned for his smooth baritone voice and charismatic presence. With over half a billion records sold, including timeless hits like “White Christmas,” Crosby was a defining figure of the Golden Age of Hollywood. His remarkable career spanned music, film, radio, and television, earning him accolades that included an Academy Award and multiple Grammy Awards.
His former mansion sits on a quiet stretch of Hillsborough’s prestigious Lower North, a French chateau hides behind towering trees and gated drives. It spans 18,535 square feet with 11 bedrooms, 10 bathrooms, a 4-vehicle garage on 5.36 acres.
The home’s architecture speaks to another time. Designed by John Bakewell Jr. and Ernest Weihe, it blends European antiques with California legacy. Bing reportedly helped select many of the home’s finer details, from Rococo plaster to millwork and imported fixtures. At one point, the grounds even held stables for Seabiscuit. Now, it’s a rare mix of Hollywood lore, racing history, and quiet grandeur… it’s currently on the market for $40 million.
Listing agent: Jenn Gilson @ Golden Gate Sotheby’s International Real via Coldwell Banker Realty
Where is Hillsborough, CA?
Hillsborough, California, is a residential town located in San Mateo County, south of San Francisco. It has no commercial zoning, with only homes, schools, and government buildings. The town is known for large estates, tree-lined streets, and strict building regulations. Hillsborough shares borders with Burlingame, San Mateo, and Interstate 280.
Entrance
The front of Bing Crosby’s former estate is as classic as it gets. A bright red arched door sits at the center of the French chateau-style facade, flanked by tall, symmetrical windows and a Juliet balcony. A brick motor court and stone balustrades complete the historic, formal look.
Entry Hall
The entryway makes a graceful first impression. Tall paneled walls in soft gray frame the space, with gold wall medallions and a crystal chandelier adding a hint of luxury. A richly patterned rug anchors the floor, while double doors open directly to the driveway and gardens beyond.
Living Room
Ornate crown molding surrounds the salon’s fireplace, which sits beneath a framed classical painting. Chandeliers hang from the ceiling, and French doors open to the outdoors. Upholstered armchairs, a baby grand piano, and a glass coffee table complete the room.
Dining Room
The dining room curves around a central chandelier, with hand-painted floral murals wrapping the walls. Tall windows and double doors open to the outside lawn. The long dining table and chairs keep the room symmetrical and ready for formal meals.
Fireplace
One of the coziest rooms in the home is a paneled sitting room with a black marble fireplace and vintage cowboy portraits. A chessboard rests on the center table, and a tall wooden ladder hints at a hidden library nearby. The room feels personal—tucked away and inviting.
Home Office
Gold records and framed plaques line the shelves in this richly paneled office, once used by Bing Crosby himself. Carved wood surrounds a central fireplace, while two large windows bring in views of the grounds beyond. A patterned rug and antique desk complete the space.
Library
Floor-to-ceiling shelves hold an extensive collection of books. The library features deep wood paneling and a full wall of windows, letting in light and green views from the outside. A white sofa and chairs form a cozy reading area around a coffee table topped with books and a potted plant.
Staircase
The main staircase rises along wood-paneled walls with carved railing and soft carpet underfoot. A tall ceiling and chandelier bring height to the space, while wood floors and soft tones tie into the classic design of the rest of the home.
Bedroom
The primary bedroom was designed for comfort and scale. A carved fireplace warms the corner, framed by gold sconces and crown molding. The bed sits beneath a dramatic upholstered headboard and canopy, with a lounge chair positioned near the windows to take in the evening light.
Bedroom
Another bedroom leans more formal. A soft blue tufted bench lines the foot of the bed, set between towering mirrors that nearly reach the ceiling. A chandelier above adds old-world glamour, balanced by warm natural light from tall French windows.
Exterior
Up close, the home’s timeworn exterior shows its charm. Faded whitewashed brick, black wrought iron balconies, and wood columns point to the building’s French influence. Stone paths lead through shaped hedges and onto the manicured grounds, once home to Seabiscuit’s stables.
Lower North Hillsborough Neighborhood
From above, the estate reveals its scale. The chateau stretches across over five acres in the Lower North Hillsborough neighborhood, tucked among towering trees with wide green lawns and long winding driveways. San Francisco Bay glimmers in the distance, just past the neat grid of neighboring rooftops.
Listing agent: Jenn Gilson @ Golden Gate Sotheby’s International Real via Coldwell Banker Realty
