Living in Hillsborough
Hillsborough sits right next door to the Burlingame neighborhoods where I grew up, and it is one of the most private places to live on the Peninsula. There are no storefronts here, just winding roads, generous lots and some of the most remarkable homes in California.
Residents voted to incorporate in 1910 to protect the town's quiet, residential character, and that vision still shapes it. Hillsborough has no commercial zoning at all. Lots must be at least half an acre, new homes must be at least 2,500 square feet, and there are no apartments or condominiums.
Daily errands are easy anyway. Downtown Burlingame and downtown San Mateo are each a short drive away, Interstate 280 runs along the western edge of town, and San Francisco is roughly 17 miles north.
Hillsborough Neighborhood Map
Every neighborhood I cover in Hillsborough, numbered and pinned.
Swipe sideways to explore the map.
Hillsborough
- 13Ryan Tract
- 14Country Club Manor
- 15Hillsborough Oaks
- 16Skyfarm
- 17Hillsborough Hills
- 18Homeplace
- 19Hillsborough Knolls
- 20Hillsborough Heights
- 21Brewer Subdivision
- 22Hillsborough Park
- 23Carolands
- 24Hillsborough Highlands
- 25Lakeview
- 26Tobin Clark Estate
- 27Parrott Drive
Each numbered pin marks a spot inside the neighborhood. Neighborhood borders on the Peninsula are informal and vary by source, so treat edges as approximate. City limits, roads and rail are drawn from OpenStreetMap. Numbers circled with a dashed line are unincorporated county areas that share a mailing city.
Neighborhood by Neighborhood
Numbers match the pins on the map above.
Ryan Tract
The flats around Town Hall off Floribunda Avenue, walkable to Burlingame Avenue and Caltrain. Homes range from 1950s ranches to Spanish villas and older estates.
Country Club Manor
Surrounds the Burlingame Country Club, which occupies the former Crocker family New Place mansion. Streets include New Place Road, Chateau Drive and Geri Lane.
Hillsborough Oaks
The far north end near Broadway in Burlingame, around Jackling, Armsby and Fagan Drives, known for 1920s and 1930s storybook homes and historic estates.
Skyfarm
Climbs west toward Interstate 280 around the Italian style Crocker mansion that has housed The Nueva School since 1971. Most homes date from the 1970s and 1980s.
Hillsborough Hills
The northwest corner off Summit Drive next to Burlingame Hills, with mostly 1950s and 1960s homes on wooded hillside lots.
Homeplace
Built on the former 130 acre Jennie Crocker estate off upper Barroilhet Drive. The land was subdivided in the 1970s, so most homes are from the 1970s through the 2000s.
Hillsborough Knolls
Mid town streets such as San Raymundo Road, La Cumbre and El Arroyo, with 1920s and 1930s revival and Mediterranean homes, many with valley views.
Hillsborough Heights
Lower Hillsborough near El Cerrito Avenue and Roblar Avenue, beside San Mateo Park. It is home to the Hillsborough Racquet Club and the Julia Morgan designed Hearst house on El Cerrito.
Brewer Subdivision
The lower south flats around Uplands Drive and Rockridge Road, close to Crystal Springs Uplands School, with storybook homes on nearby lanes.
Hillsborough Park
Midway up the south hills around Black Mountain, Vista and Chiltern Roads, with Vista Park, Crossroads Park and Richard Neutra's 1937 Hofmann House.
Carolands
Upper Hillsborough streets carved from the former 554 acre Carolan estate and centered on the Carolands Chateau, a California Historical Landmark finished in 1916.
Hillsborough Highlands
The Tartan Trail Road area between Crystal Springs Road and Black Mountain Road, where streets carry Scottish names and most homes were built from 1965 to 1979.
Lakeview
Upper Hillsborough along the Crystal Springs watershed, mostly 1950s to 1970s ranch and split level homes. The famous Flintstone House is visible from Interstate 280.
Tobin Clark Estate
The southeast hills above San Mateo, built around David Adler's 1931 English Cotswold style mansion. Most of the surrounding homes date from the 1970s through the 2000s.
Parrott Drive
A small southern pocket reached from San Mateo, near the Italian style de Guigne estate on Crystal Springs Road, with 1950s ranches and newer executive homes.
A Short History
Hillsborough grew out of Rancho San Mateo, which William Davis Merry Howard bought in the 1840s. His El Cerrito estate drew other wealthy San Francisco families, and great country houses followed, from the Crocker family's New Place and Skyfarm to the Carolands Chateau.
Residents voted to incorporate on May 5, 1910 to keep the area rural and avoid annexation. The town charter famously left out sidewalks and commercial districts, and that character remains: today the town owns about 259 acres of open space, shares the Central County Fire Department with Burlingame and Millbrae, and consistently ranks among the wealthiest communities in the country.
Schools, Landmarks and Traditions
Public Schools
The Hillsborough City School District runs North, South and West elementary schools and Crocker Middle School. High schoolers attend Burlingame, Aragon or San Mateo High depending on address.
Private Schools
The Nueva School, founded in 1967, Crystal Springs Uplands School in the Templeton Crocker mansion, and The Bridge School, founded in 1986, are all in town.
Clubs and Golf
The Burlingame Country Club dates to 1893. Crystal Springs Golf Course opened in 1924 along Interstate 280.
Concours d'Elegance
Every year since 1956, collector cars fill the fairways of Crystal Springs Golf Course for the Hillsborough Concours d'Elegance, which supports local charities including the Hillsborough Schools Foundation.
Getting Around
Interstate 280 runs along the western edge of town, downtown Burlingame and downtown San Mateo are each a short drive away, and San Francisco is roughly 17 miles north.