PENINSULA · CITY GUIDE

Hillsborough

Hillsborough is a town in the hills west of Burlingame and San Mateo, defined by large-lot zoning, winding roads, and the complete absence of a commercial district.

At a glance

  • Where it is: central San Mateo County, between Burlingame, San Mateo, and Interstate 280.
  • Known for: half-acre minimum lots, estate homes across many architectural periods, and heavy tree cover.
  • The environment: quiet, wooded, and low-density, with no sidewalks or streetlights on most streets.
  • What sets it apart: the town was incorporated in 1910 specifically to remain residential, and has no stores or offices.

Housing character

  • Large single-family homes on large lots, with a half-acre minimum in much of the town.
  • A wide range of architectural styles, from early-1900s estates to contemporary custom construction.

Places within Hillsborough

Lower North
Neighborhood closest to Burlingame with somewhat smaller lots.
Upper North
Higher-elevation streets with larger parcels and views.
Country Club
Area near the Burlingame Country Club with established estates.
Tobin Clark / Southwest
Western area with the largest parcels and the most wooded setting.

Around town

  • Residents typically use downtown Burlingame and San Mateo for shopping, dining, and services.
  • Extensive tree canopy and quiet residential roads for walking and cycling.
  • Crystal Springs watershed trails and Interstate 280 open space just to the west.
  • Community events are centered on the town's schools and civic facilities.

Getting around

  • No Caltrain station in town — residents typically use Burlingame, Millbrae, or Hayward Park in San Mateo.
  • Interstate 280 runs along the western edge; State Route 92 crosses to the south.
  • El Camino Real and US-101 are reached through Burlingame or San Mateo.
  • The town is car-dependent by design.

What to check

  • No commercial services within town — every errand means driving to a neighboring city.
  • Winding roads and hillside terrain affect access, drainage, and grading.
  • Large-lot maintenance and landscaping costs are substantial and ongoing.
  • Portions of the town carry wildfire designations that affect insurance availability and cost — check early.
  • Verify current transportation service, school assignment, permit requirements, hazard information, and total housing costs for the specific address.

Nearby guides

BurlingameTree-lined mid-Peninsula city with two Caltrain stations, a walkable Burlingame Avenue downtown, and older housing stock.San MateoMid-Peninsula city with Caltrain stations, a downtown district, and a mix of condos, houses, and hillside neighborhoods.MillbraeSmall northern Peninsula city where BART and Caltrain meet in a single station, with a walkable Broadway district.WoodsideRural-residential town in the western hills with acreage, equestrian properties, and extensive trail networks.