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WOODSIDE — With seven homes, three pools and sweeping foothill vistas over 74 acres in one of the most expensive towns in the world, Green Gables has been the Fleishhacker family’s summer oasis for five generations.
But like all things Silicon Valley, disruption is coming.
The sprawling estate built a century ago by San Francisco industrialist Mortimer Fleishhacker is on the market, pitched to be the most expensive private home sale ever in the Bay Area. Although a listing price has only been whispered — perhaps $140 million, maybe more — brokers expect the rare, historic property to fetch more than the previous record, a nearby mansion that sold for $117.5 million.
“The size alone and the location are just unparalleled,” said listing agent Michael Dreyfus. The estate is a short commute to Stanford and the venture capital firms on Sand Hill Road, and 30 miles to San Francisco.
Green Gables is perhaps one of the last grand Peninsula properties of its size to hit the market. Many of the large, 19th- and 20th-century estates in Woodside and nearby communities have either been sold to developers and divided up into affluent suburban neighborhoods, or preserved as public parks and attractions.
The Fleishhacker family has managed to keep the property as a summer retreat for five generations with a combination of smart management and a relatively small number of heirs, said Marc Fleishhacker, great-grandson of the family patriarch.The addition of newer homes on the property has also helped keep family harmony, he said.
Ownership of the property is shared by 10 family members, and the next generation includes 18 descendants. “Trying to manage a shared asset when you get to that ownership,” Fleishhacker said, “is onerous.”
But it wasn’t as difficult when patriarch Mortimer Fleishhacker started the project in 1909. Fleishhacker, a banker and founder of the Great Western Power Company, wanted a cottage and grounds to escape the chill and fog of San Francisco summers. He had his chauffeur pull over in Woodside one day, noting the fog line lifting over a vineyard.
Fleishhacker bought nine properties stretching over 74 acres. He hired noted architect Charles Sumner Greene, known for his Arts and Crafts bungalows and estate homes, to design and build an English country home. Instead of a traditional thatched roof, builders steamed and bent redwood shingles to create an undulating roofline. An enormous, freeform pool is a few steps from the house.
The main house offers a large patio and lawn for entertaining. On a lower terrace, a dramatic three-foot-deep Roman pool stretches the length of a football field and is lined with arches made of locally quarried stone. Many of the features, inside and out, were designed and hand-made in the Arts and Crafts style specifically for Green Gables.
Marc Fleishhacker spent his childhood summers on the estate. He re-enacted Roman sea battles with his cousins in the reflecting pool, learned to drive on the private roads and escorted debutantes at the local cotillions. “We would create tons of havoc,” he said.
The estate is tucked near Woodside’s town center but hardly stands out, locals say. In a town of heavy privets, iron gates and security suites, Green Gables has few impediments to its front door but speed bumps. It lacks even a gate.
“I’m sure people who live in Woodside, even some of the more recent families, don’t even know it exists,” said Barbara Wood, a local historian and journalist. “Most people know it as open space.”
That open space attracts deer, coyotes, wild turkeys, pheasants and migrating birds. There’s no hemmed in fences and few natural predators, making it an ideal enclave for wildlife. “It’s just a magical, wonderful piece of property,” Wood said.
The property hosted several family weddings, and now caters to corporate retreats. The family books a few events to help pay the upkeep on the property.
But the family members are spread across the country, and managing and preserving the estate has become more challenging.
“People used to go to Woodside because it was a nice, sunny place,” Fleishhacker said. But the influx of vast wealth — venture capitalists and tech founders brokering power deals at the local diner, Buck’s — has shifted the culture. “It’s changed.”
As development and a new Bay Area ethos has crept in, the family is ready to sell, Fleishhacker said. The decision did not come quickly or lightly. “It’s a sense of nostalgia and a sense of relief,” he said.
The property is larger and offers more privacy than other estates in the region, making it difficult to place an exact price on it, Dreyfus said. The pool of potential buyers — billionaires and big companies looking for a private retreat — is tiny.
Two other Peninsula homes have brought nine-digit sales prices. A $117.5 million, 9-acre estate in Woodside was purchased by SoftBank CEO Masayoshi Son in 2012, and, a year earlier, Russian-Israeli venture capitalist Yuri Milner paid $100 million for a luxury property in Los Altos Hills.
A new buyer will gain more than a grand private retreat. The property is listed on the National Register of Historic Places, and preserved under a conservation easement with The Garden Conservancy. It’s also in a town known for standing up against famous residents like Steve Jobs and Larry Ellison.
“It’s a million dollar view,” said Thalia Lubin, local architect and member of the Woodside History Committee. “Or a $140 million view.”
