Welcome to Woodside

Woodside is a small town full of big lots and beautiful horse properties and is one of the most wealthiest communities in the country. Much of Woodside is wooded, with Redwoods and Douglas Fir dominating the Western hills and more Oaks and Eucalyptus in the lower areas. Horses are part of the local culture and numerous residents keep horses, and the town government maintains a network of horse trails. The town is also popular among local cyclists and draws them in large numbers on weekends. Woodside is home to a number of open space preserves, including the Purisima Open Space and Filoli Gardens.
Woodside offers a quiet and historic downtown with an intentionally small business district which includes a few restaurants; a grocery store; a saloon; a hardware and horse tack store; a home and garden store; hair salon; a cleaner; and a post office. Woodside is based in San Mateo County and the population of the town was 5,287 at the 2010 census.


The Woodside area was originally home to natives belonging to the Ohlone tribe. In 1769, led by Gaspar de Portolá, Spanish explorers searching for San Francisco Bay camped at a site near Woodside. Woodside is said to be the oldest English-speaking settlement in the southern part of the San Francisco Peninsula. The first English-speaking settlers arrived in the early 19th century to log the rich stands of redwoods. Charles Brown constructed the first sawmill in Woodside on his Mountain Home Ranch around 1838. His adobe house, built in 1839, still stands today. By mid-century, the Woodside area had a dozen mills producing building materials for a booming San Francisco.
In 1849, during the California Gold Rush, 20-year-old Mathias Alfred Parkhurst purchased 127 acres of timberland and named it “Woodside"; of course, this name was kept. By the late 19th century, Woodside was home to many country estates. Woodside was incorporated in 1956 to prevent urbanization, and it still retains a rural residential character, though it is a short commute to Silicon Valley and San Francisco.
Search All Homes

Work With Us

One of the most experienced and renowned teams in the entire Bay Area, the Campi Group strives to produce the best result for every one of their clients. Buying and selling don’t have to be hard with the Campi Group on your side every step of the way.

Follow Us On Instagram