A sprawling compound with a storied past
Built in 1929, the massive home features 13,635 square feet of finished space, including 11 bedrooms, 10 full bathrooms, and five half bathrooms. The house was designed by architect John Bakewell Jr., who also helped design San Francisco City Hall.
It was commissioned by Lindsay Howard, son of Charles Howard, who owned the famous racehorse Seabiscuit. Crosby, a close friend of the family, later purchased the home.
Inside, the home is still filled with memorabilia from Crosby's career — gold records, plaques, paintings, and even his signature hats remain right where he last placed them.
"These are all memories that the family really wanted to keep within the home. This is not staged," Gilson told ABC 7.
One of the home's most interesting pieces of memorabilia is the piano used in the classic 1956 film “High Society,” where Crosby starred as C. K. Dexter Haven alongside Grace Kelly and Frank Sinatra. Despite the long legacy, the family has decided to sell after Kathryn Crosby’s passing at the age of 90.
Homes owned by celebrities often command higher prices due to their unique history, exclusivity, and cultural significance. Crosby’s mansion isn’t just a luxury property — it’s a piece of entertainment history. It may see interest from high-profile buyers looking for privacy or to own a piece of history.
Invest in real estate without the headache of being a landlord
Imagine owning a portfolio of thousands of well-managed single family rentals or a collection of cutting-edge industrial warehouses. You can now gain access to a $1B portfolio of income-producing real estate assets designed to deliver long-term growth from the comforts of your couch.
The best part? You don’t have to be a millionaire and can start investing in minutes.
Learn MoreHow everyday buyers and sellers can learn from this sale
The Crosby home is listed at a jaw-dropping amount due in part to its location, size, and cultural significance. Hillsborough, where the house is located, is known for its exclusivity, and the proximity to Silicon Valley and San Francisco makes the home an attractive option for many types of buyers.
Even if you're not in the market for a $40 million mansion, there are valuable lessons to be learned from high-end real estate trends.
Location matters
Just like Crosby's home benefits from its location near popular tech hubs, your property's location plays a key role in its future value. When making purchases, consider the school district, proximity to job hubs, and neighborhood. Also, consider how the area may change. A more affordable home in an up-and-coming area may significantly appreciate in value within just a few years.
Historic charm and unique features add value
Properties with distinctive architecture, historical significance, and unique design elements can hold or increase value over time. If you're renovating a home, look for ways to add or retain historic elements like exposed brick, arched doorways, pocket doors, or even that old laundry chute.
Emotional appeals sell
While you may not have gold records to display, staging your home to create an emotional connection with buyers can boost its appeal. Highlight unique aspects of your home that tell a story, such as a cozy fireplace, a custom-built kitchen, or a backyard perfect for entertaining on summer days. If you have older photos of your home, consider leaving a small album out for buyers to browse during viewings.
Work with experts
Whether you're buying or selling, having the right real estate agent and financial advisers can help you make smart decisions. Experts can help you navigate pricing, understand market conditions, and advise you on the right time to buy or sell.
As Bing Crosby's estate transfers to new ownership, it's a reminder that houses are much more than investments — they're a chapter in our lives. Whether you’re purchasing a luxury estate or a starter home, approach real estate with an eye to both financial insights and emotional connections.
The richest 1% use an advisor. Do you?
Wealthy people know that having money is not the same as being good with money. Advisor.com can help you shape your financial future and connect with expert guidance . A trusted advisor helps you make smart choices about investments, retirement savings, and tax planning.
Try it now
