Stretching from the popular commute route of Hwy 280 near the Venture Capital hub of Sand Hill Road, west to the summit of the Santa Cruz mountain range where one can view the ocean, lies the affluent, rural community of Woodside.    Similar to Atherton, its expensive counterpart, Woodside is home to affluent high-tech executives as well as famous entertainers. Many Woodside properties include several wooded acres allowing residents seclusion with nature.  If one is willing to forego proximity to civilization and tolerate windy mountain roads, the western most areas of Woodside become more affordable.  Where one can purchase a remote mountain retreat in the Woodside areas of Skyline, Old La Honda and Skywood for under $1 million some of the most expensive estates in Central Woodside are valued at over $50 million. Like Portola Valley, Woodside residents work hard to preserve the rustic nature and charming ambiance of their small town.  This makes for more stringent building regulations.  Considered an equestrian community, Woodside boasts one horse for every five residents.  It maintains a large trail system and has many public parks to enjoy. 


1.    Hidden Valley (near Westridge area of Portola Valley)

2.    Old La Honda Road (remote, in the hills)

3.    Skywood (remote, in the hills)

4.    Central Woodside (most expensive)

5.    Emerald Hills (shared with Redwood City, most northern and East of 280)

6.    Woodside Hills (east of 280)

7.    Woodside Glen (near 280 off Canada Road)

8.    Woodside Heights (east of 280 nearer Menlo Park)

See school information here.