A historic 74-acre compound in the hills above Silicon Valley has come on the market for the first time ever. Held in the same family for five generations, the property is one of the largest privately owned tracts of land offered in picturesque Woodside, California, a pricey enclave just 30 miles south of San Francisco and in the heart of the tech hub.

Known as Green Gables, the massive compound was created by industrialist and banker Mortimer Fleishhacker (1866–1953), in 1911, five years after the San Francisco earthquake, as a family getaway in the countryside. Seven homes in total offer 32 bedrooms, 26 bathrooms, and 23,900 square feet of living space. Fleishhacker and his wife Bella Gerstle Fleishhacker (1875–1963) commissioned the English manor-style main residence designed by brothers Charles Sumner Greene and Henry Mather Greene, California's leading proponents of the Arts and Crafts movement in the early 20th century.

Perhaps the largest of Greene and Greene's designs, the 10,000-square-foot main home features thoughtful garden overlooks, picture windows with sweeping views of the Santa Cruz Mountains setting, and intact hand-carved furniture and wood paneling depicting the four corners of the world by the Greene Brothers.

Some of the original furnishings remain in the home. According to the Christie's listing, "Famed New York interior designer Elsie de Wolfe, whose clients included Amy Vanderbilt and the Duke and Duchess of Windsor, selected and designed many of the furnishings, and her vision has been preserved to this day in three of the bedrooms."

An enormous Roman reflecting pool was built to evoke antiquity while additional swimming pools, a tennis court, artist’s studio, and barn, are among many other assets. The grounds boast old growth redwoods, spruce and live oaks, plus edible and flower gardens, formal landscapes, a lilypond, orchards, olive groves, and a reservoir for the estate's irrigation.

The other homes include a six-bedroom residence designed in the 1930s by Modernist William Wurster.

There's also a rustic two-story tea house, a home from the 1970s with a private pool, an estate manager’s cottage, and two updated structures that date to the 1860s. The property includes two private roads and wooded trails. Near the main house, "the Camperdown Elm Allée is a striking avenue of meticulously pruned trees and is considered one of the finest exemplars of its kind," reads the listing. 

Among the many events held on site, the residence hosted a gala for the 20th anniversary of the United Nations in 1965. 

While the MLS listing suggests Green Gables would be "the ultimate family compound or corporate retreat," the property's important historic and natural setting could call to a buyer with more in mind. (The property was listed on the National Register of Historic Places in 1986.) Also located in Woodside, Filoli is a historic house and garden of the same era that was donated to the National Trust for Historic Preservation in 1975. It now runs as a nonprofit that offers open hours for strolling, events, tours, a café, and educational and art programming for the public.

Co-listed by Compass and Christie’s International Real Estate, the property is currently the most expensive listing in the San Francisco Bay Area, and among very few properties priced over $100 million in the U.S.