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A small community with a population of roughly 5,500, Woodside has a lovely rural atmosphere—one that belies its status as one of the wealthiest neighborhoods in the United States.

According to information provided by Data USA, this incredibly affluent Bay Area town has a median household income of $250,000, as well as a median property value of $2 million—some of the highest in the country. In addition, homeownership in Woodside stands at an impressive 91.6%, much higher than the national average of 63.9%.

Woodside has a history of attracting the rich and famous with Bill Walsh of the San Francisco 49ers and Willie McCovey of the San Francisco Giants both having lived in Woodside. You can also add one of the most famous names of Hollywood stage and screen, Shirley Temple.

Today, some of the town’s most notable residents include Oracle chairman and co-founder Larry Ellison, technology entrepreneur Masayoshi Son, and financial executive Charles Schwab. The town is also home to the actress Michelle Pfeiffer, as well as rock artist Neil Young and folk artist Joan Baez.

Reflecting its colonial and ranching past, the majority of old houses in Woodside are built in the Spanish Colonial Revival, Mediterranean, and Provincial French Farmhouse styles. The neighborhood, however, now has its share of more modern and contemporary dwellings.

Bordered on the south and west by the Santa Cruz Mountains, Woodside is an equestrian community, and has an abundance of outdoor trails used for horseback riding, hiking, and biking.

Known collectively as the Woodside Trail System, these trails are connected to the San Mateo County Parks, as well as properties operated by the Midpeninsula Regional Open Space District (MROSD).

Woodside is also home to a thriving art scene, thanks to art programs such as the Djerassi Artists Residency, which seeks to develop and enhance artists’ skills by providing them with access to much-needed resources.

Due to its small size, Woodside does not have an actual downtown area, although it does have a selection of restaurants and department stores. Residents, however, have easy access to surrounding Silicon Valley cities should they want more shopping and dining options.

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