Howard settled his family in this area, which attracted wealthy San Franciscans.

In 1963, Jack and Betty Ken, the first-generation children of Chinese Immigrants, purchased land in the town.

This made them the first non-white people to own land in the town, effectively desegregating Hillsborough.

[7] According to the United States Census Bureau, the town has a total area of 6.2 square miles (16 km2), all of it land.

The area's considerably winding, hilly topography, and impossibility of a grid layout make Hillsborough notoriously challenging to navigate.

Many lots include fairly steep slopes, particularly the western side of the town, with the landscape generally flattening to the east as it descends from the 280 freeway to El Camino Real and the towns of Burlingame and San Mateo.

[8] Other common plants include toyon, gooseberry, lupine, monkeyflower and coffeeberry.

Commonly observed mammals include California mule deer, raccoons, opossum, coyotes, rabbits, squirrels, and skunks.

[9] Hillsborough is bordered by Burlingame to the north, San Mateo to the east, Highlands-Baywood Park to the south, and Interstate 280 to the west.

[12] The census reported that 10,825 people (100% of the population) lived in households, as no other type of residence exists in Hillsborough.

In 2019, a Bloomberg analysis ranked Hillsborough as the fifth richest town in the United States with a median household income of $373,128.

According to The Best Places to Live 2007 in Money Magazine, Hillsborough's $263,456 median household income is the highest in the country.

In 2020, the city continued to swing left, President Joe Biden won 68% of the vote and Donald Trump only managed 29%.

Primarily a residential suburb of San Francisco, Hillsborough has many mansions and other points of interest within the town's borders dating from the early 20th century.