Located on the southeast side of the San Francisco Peninsula, Woodside is among one of the wealthiest communities in the nation. Even though it was not incorporated till November 16, 1956, it’s said to be the oldest English-speaking settlement in the southern part of the San Francisco Peninsula.

The city of around 5,000 residents has some of the most unique properties in the country. A large majority of these properties are multi-acre estates that sell from the single millions to the tens of millions of dollars. A large portion of these properties also have horse stable and facilities as equestrian activities are a huge part of this community.

Coupled with this very rural feel is a quaint main strip that lines Woodside Road. Visitors can experience the iconic Pioneer Hotel, Roberts Market and the tech-deal hotspot of Buck’s Restaurant. On a short drive from civilization, residents and visitors can excuse themselves from the hustle and bustle by enjoying the fresh air of Teague Hill Open Space Preserve, Wunderlich County Park or Thornewood Open Space Reserve.