It spans 18,535 square feet with 11 bedrooms, 10 bathrooms, a 4-vehicle garage on 5.36 acres.
The homes architecture speaks to another time.
Designed by John Bakewell Jr. and Ernest Weihe, it blends European antiques with California legacy.
Jenn Gilson @ Golden Gate Sotheby’s International Real via Coldwell Banker Realty | Stefano Chiacchiarini ’74 / Shutterstock.com
Bing reportedly helped select many of the homes finer details, from Rococo plaster to millwork and imported fixtures.
At one point, the grounds even held stables for Seabiscuit.
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 Crosbys former estate is as classic as it gets.
A brick motor court and stone balustrades complete the historic, formal look.
Entry Hall
The entryway makes a graceful first impression.
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 salons 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.
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.
A chessboard rests on the center table, and a tall wooden ladder hints at a hidden library nearby.
The room feels personaltucked away and inviting.
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.
Staircase
The main staircase rises along wood-paneled walls with carved railing and soft carpet underfoot.
Bedroom
The primary bedroom was designed for comfort and scale.
A carved fireplace warms the corner, framed by gold sconces and crown molding.
Another bedroom leans more formal.
A chandelier above adds old-world glamour, balanced by warm natural light from tall French windows.
Exterior
Up close, the homes timeworn exterior shows its charm.
Faded whitewashed brick, black wrought iron balconies, and wood columns point to the buildings French influence.
Stone paths lead through shaped hedges and onto the manicured grounds, once home to Seabiscuits stables.
Lower North Hillsborough Neighborhood
From above, the estate reveals its scale.
San Francisco Bay glimmers in the distance, just past the neat grid of neighboring rooftops.
