Bing Crosby’s Historic Hillsborough Estate Hits the Market for $40M

Casey Sternsmith

If you’ve ever dreamed of owning a piece of Hollywood history nestled in the serene elegance of San Mateo County, the opportunity has arrived. 🎬🏡 The legendary Bing Crosby estate at 1200 Jackling Drive in Hillsborough is now on the market for $40 million, and it's nothing short of extraordinary.

As long-time residents and real estate experts in the Hillsborough area, the Sternsmith Group is excited to spotlight this one-of-a-kind listing. Not only does this property offer stunning architecture and luxurious amenities, but it also carries a deep legacy tied to one of the most iconic voices in American music history. 🏰📍✨


A Star-Studded Legacy 🌟🎶🏡

Built in 1929, this grand French chateau-style mansion was purchased by Bing Crosby and his wife, Kathryn Grant, in the 1960s. They raised their three children here, and the home remained in the Crosby family until this year. Following Kathryn’s passing in 2024, the estate is now being offered by their son, Harry Crosby.

From the grand staircase sourced from William Randolph Hearst’s collection to the richly carved fireplace in Bing’s study and a dazzling Venetian chandelier in the dining room—this home is a museum of elegance and history.


Estate Features & Highlights 🛋️🌲✨

  • 14,000 square feet of interior space

  • 11 bedrooms and 15 bathrooms

  • Over 5 acres of landscaped grounds

  • One-of-a-kind architectural and design elements

  • Prime location in one of Hillsborough’s most exclusive neighborhoods

It’s the ultimate blend of Hollywood grandeur and Northern California prestige.


This exquisite listing is presented by Jennifer Gilson of Sotheby’s International Realty, whose exceptional work has brought renewed attention to this historic gem. Her thoughtful marketing highlights both the property’s legacy and its modern-day elegance. 👏🏡📸


If making this property your home is a dream come true, call us today at 650-678-5455.

Casey Sternsmith

Casey Sternsmith

Founder

Get to Know Me

Meet Casey Sternsmith, founding partner of the Sternsmith Group. In business, exceptional service is what matters most to Casey Sternsmith.

With Casey at the helm of the Sternsmith Group, this level of commitment is shared by all members of the group who pride themselves on being excellent listeners with unwavering integrity, and for providing the best advocacy and negotiation skills for their buyers and sellers.

Casey’s philosophy of “love what you do, or do something else” is at the forefront of the entire team, which is evident by their true passion for helping clients achieve their real estate goals.
 
As a leader in real estate marketing, Casey employs tried and true traditional marketing as well as cutting-edge strategies such as social media marketing and professional videos for every home – from small condos to luxury estate properties. Casey’s clients also benefit from her vast personal network as a lifelong resident of the area.
 
As a result, she often achieves unprecedented outcomes for her sellers with quick sales and prices exceeding the list prices. To her buyers, Casey is known for excelling in competitive multiple-offer situations.
 
With more than 10 years of results that speak for themselves, Casey never looks at the process as a transaction, but rather as a personal decision and life choice that impact each and every day of their life. Because of this, a great deal of Casey’s personal business, and the Sternsmith Group’s as a whole, comes from repeat businesses and referrals.
 
Prior to her career in real estate, Casey owned and operated a personal training/Pilates studio in San Mateo where she honed her customer service, management, organization, and marketing skills. Combined with a bachelor’s degree from UC Santa Barbara, all of this proved to be the ideal foundation for her future success in real estate. Casey and her husband have two small children and reside in Hillsborough.
 
Tess Salter

Tess Salter

REALTOR®

Get to Know Me

Tess Salter is a top-ranked real estate agent in San Mateo County and a key leader of the Sternsmith Group, known for her exceptional negotiation skills, client-first approach, and record of delivering outstanding results. Tess has helped clients buy and sell homes across San Mateo, Burlingame, Hillsborough, Belmont, San Carlos, Redwood Shores, Redwood City, San Bruno, Millbrae, South San Francisco, Bay Meadows, Menlo Park, and Foster City. She specializes in single-family homes, condominiums, townhomes, luxury estates, and investment properties.

With over 10 years of experience, Tess has sold 71 homes in San Mateo County in 2025 and helped 61 buyers and sellers achieve over $125M in sales in 2024, according to RealTrends. Since 2015, Tess and her partner Casey Sternsmith have closed $1.3B+ in total sales, ranking them among the top 5 agents in San Mateo County and the #1 agents in San Mateo for seven consecutive years.

Tess was recognized by Gentry Magazine as one of the Top 10 Agents Under 40 in 2020, and the Sternsmith Group has been nationally recognized on The Leading 100 for the past seven years, celebrating the top-performing real estate teams in the San Francisco Peninsula.

Tess is known for her expertise in off-market listings, pre-market preparation, luxury marketing strategies, and customized property-specific marketing. She leverages Compass’ advanced technology, social media, and Facebook/Instagram Live tours to maximize exposure and deliver top results. With a strong foundation in finance, accounting, and economics, Tess provides data-driven insights that help clients make strategic real estate decisions.

Outside of real estate, Tess is deeply committed to her community. She served as PARCA Auxiliary President (2024–2025), continues on the PARCA Board (2019–2025), volunteers in Hillsborough schools, served on the West Elementary School Site Council, and chairs the Relay for Life for the American Cancer Society.

With 150+ five-star reviews and a reputation for integrity, responsiveness, and personalized service, Tess Salter and the Sternsmith Group provide exceptional guidance, strategic marketing, and unparalleled support for anyone buying or selling in San Mateo County, Burlingame, Hillsborough, and surrounding Peninsula neighborhoods.

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Insightful local knowledge and extensive expertise. We looks forward to earning your family’s trust and leveraging our success for your benefit for generations to come. We looks forward to earning your family’s trust and leveraging our success for your benefit for generations to come.

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