Woodside

Just north of Silicon Valley, yet a world apart, Woodside is one of the Bay Area’s most distinctive residential communities. With roots stretching back well before the California Gold Rush, Woodside has evolved from a logging and agricultural community into an enclave of extraordinary country estates, rustic luxury, equestrian traditions, and protected natural beauty. Despite its proximity to one of the world’s most important centers of technology and finance, Woodside retains a rural character and sense of privacy that make it a retreat from the intensity and pace of Silicon Valley.

During the Gold Rush era, Woodside became an important source of lumber for the construction boom in San Francisco, approximately 30 miles to the north. As the 19th century progressed and the sawmills gave way to farms, ranches, orchards, and vineyards, prosperous San Francisco families were drawn to Woodside’s beautiful landscape and began establishing magnificent country estates among its oak-covered hills and redwood forests. By the 1880s, the tradition of the grand Woodside country estate was firmly established.

Several of these historic properties remain important parts of Woodside’s identity. Filoli, completed in 1917 for William and Agnes Bourn, is one of the finest surviving country estates of the early 20th century and became internationally recognizable through its use as a filming location, most famously in the television series Dynasty. Green Gables, the historic Fleishhacker family estate designed by Charles Sumner Greene, is another celebrated Woodside property. The monumental Buck Estate, inspired by England’s Hampton Court, is yet another reminder of the extraordinary estates created here. The wooded lands of the historic Phleger Estate are now preserved as part of the Golden Gate National Recreation Area.

Today, Woodside is one of the Bay Area’s most affluent and expensive residential communities. Its upper end has produced some of the most extraordinary residential transactions in the country. A Woodside estate sold for $117.5 million in 2012, while historic Green Gables sold for $85 million in 2025, making it the Bay Area’s most expensive publicly reported residential sale that year. Eight-figure estate sales illustrate just how dramatically the value of Woodside property has risen while the town has continued to protect its rural character.

Yet Woodside is not composed solely of immense estates. There are also enchanting residential neighborhoods with a more intimate scale. Woodside Glens, for example, was originally subdivided in the 1920s, when its lots were marketed as sites for second homes and vacation cabins for San Franciscans. Today it remains a distinctive neighborhood within the larger Woodside community.

Throughout Woodside, tranquil lanes meander beneath canopies of oaks and redwoods. Many of the larger estates are secluded from the road, approached by long private driveways and protected by stone walls, rustic fencing, or gates. Private vineyards, olive orchards, pastures, corrals, barns, and gardens dot the gently rolling terrain, reinforcing the feeling that Woodside remains a country community despite its location at the heart of the Peninsula.

Woodside’s architecture reflects this setting. In addition to its grand historic estates, homes are often interpretations of Craftsman, farmhouse, ranch, early California, and contemporary styles. The community includes landmark haciendas, ranch houses, and modern residences by notable designers and architects including Cliff May, Gardner Dailey, and William Wurster. Woodside’s longstanding emphasis on local land-use control and preservation has helped protect the open space, low-density development, and rural atmosphere that distinguish the town from much of the surrounding Peninsula.

Reflecting Woodside’s laid-back culture is its small and charming town center. Longstanding local institutions include the Pioneer Saloon, Buck’s of Woodside, Roberts Market, Roberts Hardware, Tack & Feed, and the Michelin-starred Village Pub. Historic sites include the Woodside Store, now preserved as a San Mateo County museum, as well as the Woodside Community Museum. Together, these businesses and historic buildings help retain the informal village character that has long defined central Woodside.

Beyond the town center are other longtime destinations, including the Skywood Trading Post, the Mountain House, and Alice’s Restaurant, a landmark gathering place among the redwoods on Skyline Boulevard. Alice’s has been part of the mountain community for generations and remains especially popular with locals, hikers, equestrians, bicyclists, and motorcyclists.

Horses play a significant role in Woodside’s culture. The community has a long tradition of equestrian estates and of Thoroughbred, carriage, and steeplechase horses. Horse trails wind throughout the area, and hitching posts remain part of Woodside’s streetscape. The Town itself describes its character as “trails, not sidewalks” and “hitching posts, not stop lights.” The Horse Park at Woodside, situated on more than 270 acres, provides extensive equestrian facilities including arenas, cross-country courses, an exercise track, trails, and a polo arena. Walking, horseback riding, and bicycling remain an integral part of Woodside life.

Within and immediately surrounding Woodside are thousands of acres of parks, preserves, forests, meadows, creeks, trails, and mountain ridges. Deer, coyotes, bobcats, squirrels, and other wildlife are common, while mountain lions are occasionally seen and birds of prey can often be spotted above the hills. The towering redwoods of the Santa Cruz Mountains and the native oak-covered hillsides create a landscape that feels remarkably removed from the urban communities only minutes away.

Woodside nevertheless offers convenient access to the Peninsula and the greater Bay Area. Stanford University, Stanford Shopping Center, Sand Hill Road, and Menlo Country Club are all nearby. Sand Hill Road is internationally known as a center of venture capital and private equity, while Fisher Investments continues to maintain a corporate office in Woodside itself. San Francisco and San Francisco International Airport are approximately 30 miles away, and California’s wine country, Pacific Coast beaches, and Carmel are all within reach for day trips.

Education is another important part of the area. Woodside Elementary School serves students through eighth grade, while Woodside High School serves the greater community at the secondary level. Esteemed private schools nearby include Woodside Priory and Menlo School, and Stanford University is only a short distance away.

Woodside’s extraordinary privacy, natural beauty, and proximity to Silicon Valley have long attracted leaders in technology, finance, entrepreneurship, and the arts. Among those closely associated with Woodside over the years are Oracle founder Larry Ellison, technology entrepreneur Tom Siebel, Intuit co-founder Scott Cook, singer and artist Joan Baez, and musician Neil Young. Rather than existing apart from Woodside’s rural traditions, many of these residents have been drawn to precisely the privacy and natural environment that the community has worked so carefully to preserve.

Woodside has also long attracted artists, architects, and musicians inspired by its landscape. Woodside-based artist and architect Jim Caldwell, for example, has spent decades painting the California landscape from his studio beneath the redwoods. The beauty of Woodside’s oak- and redwood-covered hillsides and mountains continues to inspire a strong artistic presence in the community.

Reflecting the romance of the Old West and the American spirit, Woodside can feel like a step back to an earlier, simpler time. That contrast is perhaps what makes it most remarkable: some of the most valuable residential real estate in the country and some of the most influential figures in modern technology and finance coexist with horses, barns, narrow country roads, towering redwoods, historic estates, and vast stretches of open land. Woodside remains a laid-back retreat from nearby Silicon Valley and a place truly unlike any other.

Long before European settlement, the area that became Woodside was home to Ohlone/Costanoan people, who lived among its creeks and forested valleys. Spanish explorers led by Gaspar de Portolá passed through the region in 1769. Following Mexican independence from Spain, much of the surrounding land became part of Mexican land grants, including Rancho Cañada de Raymundo.

Some of the first English-speaking settlers on the San Francisco Peninsula arrived in the Woodside area during the 1830s. Charles Brown established an early sawmill on Mountain Home Ranch, while cattle ranches, farms, and small settlements gradually developed throughout the area.

The discovery of gold in California and the rapid growth of San Francisco dramatically increased demand for lumber. In 1849, Dr. Robert Orville Tripp and M.A. Parkhurst entered the lumber business with San Francisco builders and helped establish a direct route for transporting Woodside lumber toward Redwood Creek and San Francisco. By 1855, at least eight sawmills and a shingle mill were operating in the Woodside area.

As the forests closest to settlement were logged, the character of Woodside gradually changed. Sawmills gave way to farms, cattle ranches, orchards, and vineyards. By the 1880s, prosperous San Francisco families were establishing country estates in the area, beginning the transformation that would eventually make Woodside one of the Peninsula’s most prestigious residential communities.

The 20th century brought enormous growth to San Mateo County and, eventually, Silicon Valley. Woodside residents responded by working to preserve the community’s rural landscape and local control over development. In 1956, voters chose to incorporate Woodside as a town, placing road maintenance, planning, and zoning under local control. Those responsibilities remain central to the Town today.

Through all of these changes, Woodside has remained unusually committed to preserving its natural environment, historic properties, equestrian heritage, and rural character. That commitment, combined with its proximity to Stanford University, Sand Hill Road, and Silicon Valley, has made Woodside one of the most distinctive and sought-after residential communities in California.