Steeped in natural privacy because of its hilly setting, Hillsborough has become a prized retreat for Bay Area residents seeking a relaxed lifestyle. Since it is located between business hubs like San Francisco and Palo Alto, this exclusive town integrates sought-after centrality with a luxurious sense of seclusion.
An Outstanding Past
Hillsborough offers a renowned history stemming from the efforts of one leading family. William Howard, the heir of an East Coast-based shipping empire, moved into the region in the 1840s and purchased a vast amount of land to form a working ranch. The Howards prospered throughout the Gold Rush and subsequently grew into one of the most prominent families in the area. By the end of the Civil War, the family ranch had been split into many smaller estates, which drew the attention of neighbors like San Mateo and Burlingame. These communities wanted to annex the estates to accommodate swelling population sizes. In 1910, owners of the smaller estates voted to incorporate, saving them from threats of annexation.
Many of these smaller estates were further reduced in size over time; in the case of properties like Uplands and Sky Farm, some were eventually converted into prestigious private academies. Though the expansive nature of its original estates may be lost to history, present-day Hillsborough maintains regulations that preserve its spacious character and attractive privacy. Lots must be at least one-half acre, and zoning ordinances require each residence to be a minimum of 2,500 square feet. An absence of commercial zoning means there are no local apartments, condominiums, or businesses, making Hillsborough seem reminiscent of a quiet, country hamlet of the past.
The town of Hillsborough is a prime enclave for those who wish to have easy access to both “the City by the Bay” and Silicon Valley. In addition, the community historically has attracted elite inhabitants with its temperate climate and privacy. Money magazine has ranked Hillsborough as the most affluent town in the country, and in 2019 Bloomberg listed it in the top five richest towns in America.
An Enjoyable Community
The roughly 11,000 residents who inhabit Hillsborough enjoy the bucolic nature of the town and the tranquility and space it provides. The local population is tightly knit and hosts annual events such as holiday parades and the Hillsborough Concours d’Elegance, where vintage car owners proudly displace their prized vehicles.
A Sterling Education
Hillsborough has its own highly regarded public elementary and middle schools, while high school students can attend schools within the San Mateo Union High School District. Also nearby are several premier private schools, including the Nueva School, Bridge School, and Crystal Springs Uplands School.
The calm demeanor, distinguished history, and desirable seclusion offered by tony Hillsborough are features that make this enclave as special at it is exclusive. Its large estate homes on spacious lots and relaxed, rural atmosphere provide an excellent sanctuary for those who enjoy luxury, peace, and privacy.
Notable Residents—Past and Present
Patrick Burrell, San Francisco Giants MLB player, two-time World Series champion
Jenny Craig, weight-loss guru
William H. Crocker, founder and president of Crocker National Bank
Bing Crosby, singer and actor
William Randolph Hearst, leading newspaper publisher
Larry Probst, chairman and former CEO of Electronic Arts
Alicia Silverstone, actress
J.T. Snow, San Francisco Giants MLB player, radio and television broadcaster
George Tupou V, King of Tonga
The public schools are among the best in the nation. Graduates from the local high schools attend the most prestigious colleges and universities in the country, with a much larger than average number admitted to neighboring Stanford. Abundant bike paths make it easy for most students to bike to their local schools, giving them a sense of independence that is valued by parents and children alike.