Welcome to Woodside
Woodside residents value secluded, outdoor living and a strong sense of community. The Santa Cruz Mountains separate the town from the ocean. Towering redwoods cover the western hills, with oaks and eucalyptus lower down.
Settlers arrived in the early 1800s to log the redwoods. Later, San Francisco families built country estates here, and regular stagecoach service to the city began in 1852. Farms, cattle ranches and vineyards replaced the sawmills, and vines still cover many hillsides. After World War II, residents worried that growth would turn their rural haven into a suburb. They incorporated in 1956 to keep local control, and it worked.
Today Woodside is a town of trails, horse properties, open space and summer jazz at Filoli. On weekends, cyclists fill Cañada Road, Old La Honda Road, Kings Mountain Road, Skyline Boulevard and Highway 84. Huddart County Park, Wunderlich Park and the Phleger Estate are all close by.
The small town center has Roberts Market, a hardware and tack store, and a few restaurants, including Buck's of Woodside, where more than a few venture deals have been sketched on a napkin.
What Makes Woodside Different
- The Land. Large parcels, many an acre or more, with room for horses, gardens and real privacy.
- The Outdoors. Horse trails, open space preserves and some of the best cycling roads in the country, right from the front door.
- The Town. A small, unhurried town center, with Roberts Market, Buck's and the Village Pub.
Neighborhoods in Woodside
Central Woodside
Woodside's most sought-after area. Large, sunny, very private properties, many close to town and in the Woodside Elementary School District, with views of the foothills and open space. Horse owners enjoy the trail network that runs through it.
Woodside Glens
Once vacation cottages and housing for workers on the local estates, "The Glens" is now a close-knit neighborhood of people who like knowing their neighbors. Downtown Woodside and Woodside Elementary School are within walking distance.
Woodside Hills
About 250 homes northeast of Highway 280, north of Woodside Road and west of Alameda de las Pulgas. Lots are a minimum of one acre, many with views of San Francisco Bay, and a homeowners association guides land use and architecture.
Woodside Heights
On the southeast side of Woodside Road between Alameda de las Pulgas and Highway 280, in the Las Lomitas School District. Lots of an acre or more, quiet roads and wooded hills give real privacy with an easy commute.
Hidden Valley
Tucked between Jasper Ridge Biological Preserve and Portola Road, Hidden Valley is quiet and full of open space and wildlife. Portola Valley's Town Center is a minute or two away, yet the area somehow stays hidden.
Old La Honda Road
Everything from old cabins to large new estates, in heavily wooded hills with views of the Bay. The winding road through oaks and redwoods is a favorite climb for local cyclists.
Skywood
From Skyline Boulevard down toward town, Skywood's homes look out over the Bay. Large lots and wooded hillsides blend neighborhood and rural living.
Skyline
Skyline is a lifestyle. A short drive up the hill and you feel a world away from Silicon Valley. The sunny days are brighter and the winter storms are stronger. Alice's Restaurant is the weekend meeting place for drivers and cyclists.
Kings Mountain
On Skyline Boulevard just south of Highway 92, Kings Mountain is rural and full of redwoods, with ocean views from many homes on a clear day. Homes range from rustic to new custom, and the annual Kings Mountain Art Fair supports the local school and fire department.
Emerald Hills
Just outside the Town of Woodside, next to Cañada College and Edgewood Park, Emerald Hills has winding roads, acre lots and trails for hiking, running and riding. Homes range from 1940s summer cottages and ranch homes to new custom builds and horse properties.
Selling in Woodside
Woodside sales take local knowledge. Wells, septic systems, private roads, trail easements and horse facilities all affect value, and the right buyer may be local, across the country or overseas.
Many Woodside sellers also value discretion. Whether you want broad exposure or a quiet, targeted sale, I build the plan around you and keep you updated every week.
Homes for Sale
Questions About Woodside
When did Woodside become a town?
Woodside incorporated in 1956, largely to protect its rural character.
Which schools serve Woodside?
Much of the town is served by Woodside Elementary School District, a single-school district. Some areas, such as Woodside Heights, are in other districts, so always check a specific address.
Is Woodside good for horses?
Yes. Woodside has an extensive network of horse trails, many horse properties and boarding facilities, and the Horse Park at Woodside.
Are Emerald Hills and Kings Mountain part of Woodside?
No. Both are unincorporated San Mateo County, close to the Town of Woodside and often grouped with it.
