Woodside residents value secluded outdoor living while enjoying a strong sense of community. Separated from the ocean by the Santa Cruz Mountains, towering redwoods dominate its western hills, with oaks and eucalyptus in the lower areas. Residents value its privacy, access to nature, large parcels of land and diverse architecture.
Settlers arrived in the early nineteenth century to log the rich stands of redwoods. Later, prosperous San Francisco families built country estates in Woodside with regular stagecoach service to San Francisco established in 1852. Farms, small cattle ranches and vineyards replaced the sawmills and its hillsides and steep ravines are now filled with vines, tended by notable winemakers such as Thomas Fogarty. Rapid growth after World War II alarmed local residents, who feared that their rural haven would be transformed into an urban area. Residents incorporated in 1956 to retain local control and stop urbanization.
This town of just over 5,000 enjoys a rural lifestyle with local trails, horse properties, open space preserves, an artists’ colony and summer jazz at the beautiful Filoli Garden. Popular cycling routes draw cyclists in droves on the weekends along Cañada Road, Old La Honda Road, Kings Mountain Road, Skyline Boulevard and Highway 84. Woodside is also home to several open space preserves, including Purisima Open Space, Huddart County Park, the Phleger Estate and Skeggs Point.
The small business district includes Roberts Market, a hardware and horse tack store, and a few restaurants, including the iconic Buck’s of Woodside, where many venture capital deals have been inked. Woodside is home to a mix of Silicon Valley movers and shakers – CEOs and venture capitalists, as well as famed musicians and artists.
Woodside Hills is a community of 252 homes located in the Town of Woodside to the northeast of 280, north of Woodside Road and west of Alameda de las Pulgas. The homes are situated on minimum one-acre lots, many with views of San Francisco Bay. A homeowners association governs land use, and architectural design.
Woodside Heights sits on the southeast side of Woodside Road between Alameda and 280, in the highly-regarded Las Lomitas School District. With lots generally one acre or more, it combines the woodsy, rural feel of Woodside with a convenient location. The combination of quiet roads and hilly, tree-covered terrain offers great privacy for residents.
Originally an area for vacation homes and employee housing for workers on the local estates, “The Glens” has evolved into a closely knit community of residents who value knowing their neighbors and small town living, while being within walking distance of downtown Woodside and enjoying easy access to Woodside Elementary School.
Central Woodside is the most expensive part of Woodside with large, sunny, very private properties, with many close to town and in the Woodside Elementary School District. Many of the homes have views of the foothills and open space. Horse owners enjoy the network of trails that runs through the area.
The Hidden Valley/Family Farm area is nestled between Jasper Ridge Open Space Preserve and Portola Road. Residents enjoy the quiet seclusion with ample open space that attracts many wild animals. Just a minute or two from Portola Valley Town Center, Hidden Valley is a convenient location that somehow manages to remain hidden.
Old La Honda Road
Old La Honda features a wide variety of homes, from older cabins to newer large and luxurious properties. Tranquility abounds in this heavily wooded area and many properties have beautiful views of Silicon Valley and the San Francisco Bay. The quiet road winding through oaks and towering redwoods is a popular route among local cyclists.
The Skywood neighborhood borders Skyline Boulevard on its upper, western edge and drops down the hill toward the town of Woodside, offering homes there stunning views of the Bay. The large lots and heavily treed hillsides offer space and privacy for the residents, making for a nice blend of neighborhood and rural feel.
Skyline is a lifestyle. A short drive up the hill and you feel a world away from the frenzy of Silicon Valley below. Weather is more varied up in the mountains – the sunny days are brighter and the winter storms are stronger. Skyline Boulevard, with its iconic Alice’s Restaurant, is a popular weekend destination for motorists and cyclists.
Emerald Hills sits adjacent to Cañada College and Edgewood Park on the east side of 280. The neighborhood feels rural, with windy roads, many acre lots, open space, hiking, running and horse trails. The diverse architecture includes former summer residences from the 1940s, smaller ranch homes, new large custom homes, and horse properties.
This neighborhood is located on Skyline Boulevard just south of Highway 92. On a clear day, many properties have ocean views. It is very rural, with lots of redwood trees. There is a variety of lot sizes and architecture, from rustic homes and newer custom homes. Residents enjoy the annual Kings Mountain Art Fair, organized in support of the local school and fire department.
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