Welcome to Woodside
Incredible affluence and a wealth of equestrian amenities attract much of California’s elite to this sprawling country paradise
Surrounded by vast open space preserves and rolling hills in the lush shadow of the Santa Cruz Mountains, Woodside is a small town abounding in opulent estates. A reputation as being a lavish, exclusive enclave precedes Wood, drawing tech CEOs and high-profile investors to its sought-after central location on the San Francisco Peninsula.
Woodside’s history begins with its original inhabitants, the Ohlone Tribe, followed by Spanish exploration in the 1700s. Eventually, the town was incorporated in 1956. Despite its close proximity to Silicon Valley, Woodside has retained its rural atmosphere. Contributing factors such as a dedication to preserving open space, keeping a small business district, and favoring larger lots for residential real estate all help Woodside keep an agrarian charm.
Extravagant, multimillion-dollar homes are the norm in Woodside, with a great deal of real estate best described as luxury country properties. With vast land, stables and trails for horses, mansion-sized interiors, and jaw-dropping resort amenities, some of the palatial homes at the top echelon of Woodside can cost a whopping 100 million or more. From historic European-style estates to hillside contemporary masterpieces with no expenses spared and Tuscan mansions complete with a vineyard, the homes in Woodside are nothing short of remarkable.
What to Love
A plethora of trails for hiking, biking, and horseback riding
Mind-bogglingly beautiful estates and residential properties
Just 30 minutes from major hotspots like San Francisco, San Jose, and Palo Alto
Woodside is all about nature-meets-elegance, and homes here are designed to invite the outdoors inside in the most striking ways. Though it’s ranked among the wealthiest zip codes in the nation, Woodside isn’t overrun with a bustling commercial district or heavy traffic of tourists. Quality over quantity runs true here, evidenced by Michelin-starred restaurants and supply stores specific to the needs of the town’s residents.
Dining, Entertainment, Shopping
Woodside might be separated from the urban thrum of bigger cities on the San Francisco Peninsula, but that doesn’t mean its residents are left bereft of options for dining and shopping. In town, boutiques like Emily Joubert
provide exquisite gifts for all occasions and curated items for home and garden.
When exploring the restaurants of Woodside, diners might witness historic deals between venture capitalists or the meetings of major tech giants. Buck’s of Woodside
, for instance, is revered as an iconic Silicon Valley restaurant for its frequent notable patrons and entrepreneurs. Buck’s menu of sumptuous comfort food is paired with whimsical, eclectic décor, establishing a refreshingly low-key ambiance.
Those in search of absolute culinary excellence need look no further than The Village Pub
, a Michelin-rated restaurant specializing in seasonal New American fare sourced with a dedication to farm-to-table style cuisine. If you’d rather craft your own dish at home, there’s the fine selection of meats, produce, gourmet groceries, and wines at the old-school butcher, Roberts Market
Things to Do
Rich in natural resources, much of the activity in Woodside is centered around enjoying the great outdoors. Equestrian trails
exist throughout the entire town, well-marked and suited for varying levels of expertise. There are plenty of facilities for the sport, as well, such as the unique Pacific Coast Equestrian Vaulting Club
or the boutique barn, Sandhaven Farm
The San Francisco Peninsula is brimming with vineyards and wineries, and among them is Woodside’s very own, award-winning Dreyer Family Wine Company
. Locals can join the Menlo Country Club
and partake in a leisurely round of golf before hitting up the town’s fine dining, or alternatively spend the day at one of the many open-space preserves and parks. The Teague Hill
preserves — perched in the hills above Woodside — are particularly popular for hiking and horseback riding.
- Woodside is home to a number of excellent schools. Top educational opportunities include:
- Woodside Elementary School, K-8, highly rated public elementary school with a private pre-school on campus, rated as the #3 best public elementary in the entire state
- Woodside High School, 9-12, highly rated public magnet school rated among the top 10 in the San Francisco Bay Area