The town of Hillsborough, formed when members of the Burlingame Country Club decided that the Village of Burlingame was becoming too commercial, sits on land that was part of Rancho San Mateo, William Davis Merry Howard’s vast property purchased from the Mexican governor Pio Pico in 1846. The Rancho was so large that after Howard’s death, the land was parceled into plots large enough to serve as estates for wealthy San Francisco businessmen who wanted to live “in the country” and commute p to the city.
Several of the original mansions still stand today. Harriet Pullman Carolan, the heiress to the Pullman Railway Car fortune, built Carolands and it remains as one of the largest private residences in the United States today. William Crocker, grandson of Charles Crocker, built Skyfarm in 1930. Today it houses
Nueva Day School. Crystal Springs Uplands High School was originally the Uplands mansion, a gift of Templeton Crocker to his fiancée Helene Irwine , heiress to the C&H Sugar fortune in 1912.
William Randolph Hearst built the “Western White House”, a mansion of similar structure to his Heart Castle, and it is currently privately owned.
Today, Hillsborough is still renowned for its wealth and diversity. The trees and wooded hillsides add to the towns beauty. The three elementary schools and one intermediate school score among the highest scoring
in the state. The town sits just above El Camino Real and below 280. Most homes are in the hills and many have beautiful views of the bay, San Francisco and the canyons.
There is no downtown, no industry, and only one park. When the town incorporated in 1910, they
passed zoning laws forbidding any business and practically none exist there even today. There is one golf course across 280 abutting the Crystal Springs Reservoir, a racquet club and several private schools. Residents are orientated to Burlingame or San Mateo for most of their shopping. Hillsborough is truly a bedroom community.