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 outlined. Tap an area to open its guide.
Disclaimer: neighborhood borders shown on this map are approximate. Neighborhoods on the Peninsula have no official boundaries and names and lines vary by source. These shaded areas follow San Mateo County Assessor parcel lines, grouped by the original subdivision tracts, and city limits come from San Mateo County GIS. They are for general reference only and are not official city, school or MLS boundaries, so please confirm the neighborhood, school assignment and jurisdiction for any specific address. Freeways, El Camino Real and Caltrain come from San Mateo County GIS. Numbers circled with a dashed line are unincorporated county areas that share a mailing city. Tap any area to open its neighborhood guide.
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, Country Club 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 Crocker mansion that has housed The Nueva School since 1971. Most homes date from the 1970s and 1980s.
Hillsborough Hills
The northwest corner next to Burlingame Hills, with 1950s ranch homes and newer estates on wooded hillside lots.
Homeplace
Built on the former 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 homes and Bay and valley views.
Hillsborough Heights
Lower Hillsborough flats near El Cerrito Avenue and San Mateo Park, close to South Hillsborough School 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, with many 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 historic de Guigne estate on Crystal Springs Road, with 1950s ranches and newer custom homes.
Video Tours in Hillsborough
A Hillsborough estate I walked through on camera. Press play for a quick look inside.
Hillsborough estate on more than two acres
Watch on Instagram →
A Short History
Hillsborough grew out of Rancho San Mateo, which William Davis Merry Howard bought in the 1840s. Other great country houses followed his El Cerrito estate, 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 has no commercial zoning and shares the Central County Fire Department with Burlingame and Millbrae.
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 just over the line in Burlingame, along Interstate 280.
Concours d'Elegance
Since 1956, collector cars have filled the fairways of Crystal Springs Golf Course for the Hillsborough Concours d'Elegance, which supports local charities including the Hillsborough Schools Foundation.
Hillsborough Market Report
Home sales for Hillsborough pulled directly from MLSListings, the Bay Area's MLS: how many homes sold, what they sold for, and price per square foot.
Last 30 days
September 26 to October 25, 2026
Last 90 days by home type
July 28 to October 25, 2026
| Home type | Homes sold | Median price | Median price per sq ft |
|---|---|---|---|
| All homes | 26 | $6.15M | $1,585 |
Last 12 months, single family homes
October 26, 2025 to October 26, 2026.
Source: MLSListings closed sales for Hillsborough, CA, all residential property types, as of October 25, 2026. Information deemed reliable but not guaranteed. Ask me for a full report on your street or price range.
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.
Hillsborough FAQ
What neighborhoods are in Hillsborough?
This guide covers 15 Hillsborough neighborhoods, including Ryan Tract, Country Club Manor, Hillsborough Oaks, Skyfarm, Hillsborough Hills and Homeplace. See the map above for boundaries and a short write-up on each.
What schools serve Hillsborough?
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, all in the San Mateo Union High School District.
Does Hillsborough have a Caltrain station?
No. Hillsborough is almost entirely residential, so residents use the nearby Burlingame and San Mateo Caltrain stations. Interstate 280 runs along the west side of town.
What is my Hillsborough home worth?
Every Hillsborough street prices a little differently. Request a free home valuation and Joseph will send a local estimate based on recent nearby sales. Request a free home valuation
How can I hear about Hillsborough homes before they hit the market?
Join Joseph's off-market list. You'll hear about coming-soon and off-market homes that match what you want before they're listed publicly. Join the off-market list
Sources
The facts on this page come from the public sources below. Neighborhood names and borders vary by source, and details like school assignments change, so please confirm anything important for a specific address.
- Wikipedia: Hillsborough, CaliforniaIncorporation May 5, 1910; 2020 population 11,387; half acre lots, 2,500 sq ft minimum homes; Howard and Rancho San Mateo
- San Mateo Daily Journal: Hillsborough, a collection of country cottagesBurlingame Country Club founded 1893; charter restrictions; Town Hall history
- Hillsborough City School District: About HCSDNorth, South and West schools and Crocker Middle School
- Central County Fire Department: AboutFire service shared with Burlingame and Millbrae
- The Nueva School: HistoryFounded 1967; Crocker mansion campus since 1971
- The Bridge School: Our Founding StoryFounded 1986 in Hillsborough
- Wikipedia: Crystal Springs Uplands SchoolTempleton Crocker Uplands mansion
- Wikipedia: Carolands554 acre estate, completed 1916, California Historical Landmark No. 886
- PCAD: New Place, Burlingame Country Club clubhouseCrocker family New Place mansion as country club
- PCAD: Skyfarm, Nueva SchoolSkyfarm mansion and Crocker estate
- PCAD: Tobin Clark EstateDavid Adler's 1931 mansion
- Wikipedia: Arthur and Mona Hofmann HouseRichard Neutra's 1937 Hofmann House
- Wikipedia: Flintstone HouseFlintstone House visible from I-280
- San Mateo Daily Journal: Crystal Springs Golf CourseCourse opened 1924
- The Shop Magazine: Hillsborough Concours marks 70 yearsConcours began 1956; benefits Hillsborough Schools Foundation
- MLSListings: closed sales data for the market reportMarket report figures
Header photo: Carolands Chateau by Gary (gary gary gary at English Wikipedia), Wikimedia Commons, licensed CC BY 3.0.
Hillsborough Market Trends
Market Trends are calculated using MLS® sold listing data
