Woodside

Welcome to Woodside

Woodside doesn't have the polished origin story of an Atherton or a Hillsborough. It started out as a rough logging town: by 1855 it had eight sawmills and a shingle mill, and Whiskey Hill Road got its name from the saloons that once lined it. Wealthy San Franciscans didn't discover Woodside until the 1880s, when they began building weekend estates there. Once they arrived, they stayed.

Today Woodside is one of the wealthiest towns in the country, but it's held onto its rural character. Weekends bring out road cyclists and equestrians in equal numbers, enough that it's normal to see both bicycles and horses tied up outside Roberts Market, still the town's unofficial meeting place. Woodside has three equestrian organizations, including the Woodside-area Horse Owners Association, known locally as WHOA.

Unlike Atherton and Hillsborough, Woodside allows businesses within town limits, though it's never had a traditional downtown. Instead, most of it is clustered along Woodside Road between Whiskey Hill and Cañada Road: Roberts Market, a handful of shops, and restaurants including Buck's, still run by the MacNiven family and still known for its whimsical décor as much as for the number of Silicon Valley deals that have supposedly been struck there over pancakes.

A few hundred feet from Buck's sit Woodside Town Hall, Independence Hall, and the Pioneer Saloon, the last surviving nightspot from Whiskey Hill Road's early days. Further down the road, the Woodside Store is preserved much as it was in the 19th century. Nearby Filoli, a historic estate and garden, is now a museum and public garden, and one of the most visited historic sites on the Peninsula.

Woodside has fewer than 5,500 residents, but its town limits stretch all the way into the Santa Cruz Mountains, so it's possible to live close to Highway 280 or miles from your nearest neighbor, surrounded by redwoods. Two of San Mateo County's largest public parks, Huddart Park and Wunderlich County Park, sit within town limits, with miles of trails between them.

The town's sense of community shows up in how people spend their time: riding, biking, joining WHOA, and turning out for the annual Kings Mountain Art Fair and the Woodside School Auction, which raises significant money each year for the town's only public school. Over the decades, Woodside has been home to figures like Steve Jobs, Larry Ellison, Charles Schwab, Michelle Pfeiffer, Joan Baez, Intel co-founder Gordon Moore, and former Congressman Pete McCloskey, evidence of how long this small town has drawn outsized attention without losing its rural feel.

Not all of Woodside sits west of Highway 280. Woodside Hills, on the east side of the freeway toward Redwood City, is part of town too, with its own mix of view-lot homes convenient to both downtown Woodside and Redwood City. It's a quieter, less-known corner of Woodside, but every bit as much a part of it.

Woodside is a genuinely unusual market: enormous lots, real privacy, and a community that still organizes itself around horses and bicycles rather than storefronts. I've sold homes here myself, including a Bay-view property in Woodside Hills, and I bring the same approach to every part of town: careful preparation, honest advice, and a clear sense of how acreage, access, and privacy affect value. If you're comparing Woodside to Portola Valley or Atherton, or trying to figure out how a Woodside Hills property stacks up against one closer to downtown, I'm glad to help you think it through.

- Caroline