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The Midpeninsula has no shortage of seriously unique homes. From family wineries and historic estates to modern mountain retreats, these one-of-a-kind properties – whether because of their price, unusual design or history – are notable even for Silicon Valley. Every month, we highlight some of these not-so-ordinary properties that are on the market right now, or recently sold. This week, we take a look inside a Tuscan-inspired family compound on the market for $65 million in Portola Valley.
Tuscan-inspired property with 3 houses
Built in 2021, this Tuscan-inspired property comes with multiple structures spread across 12 acres in Portola Valley’s Westridge neighborhood. Known as Villa del Prato (“House of Doors”), the estate includes a two-level, 12,305-square-foot main residence with a 3,500-bottle wine cave; a 6,500-square-foot entertainment house; and a 2,000-square-foot pool house with guest quarters, providing more than 20,000 square feet of total living space. Each building in this family compound sits on its own lot with its own address.
Due to strict zoning rules and an emphasis on preserving the town’s rural character, this three-parcel lot is somewhat of a rarity in Portola Valley.
A billionaire developer’s retreat
Once the home of the late billionaire real estate magnate Walter Shorenstein, who was reportedly the largest landlord in San Francisco at one time and a top Democratic donor and adviser to several U.S. Presidents, the property was a popular destination for many notable guests, including former President Bill Clinton, The Almanac previously reported.
In 2013, the town permitted the new owners to subdivide the land into three lots, allowing them to make additions to the property, which had reached its maximum square-footage limits as a single parcel under the town’s newer and stricter laws.
The new owners chose to build their main residence in the original location of the former home, preserving much of the landscaping, including the redwood grove in which the main drive gently weaves through, according to listing agent Chris Iverson of Golden Gate Sotheby’s International Realty.
The great room. Photo by Matt Anello, courtesy Chris Iverson. 
The exterior of the main home. Photo by Matt Anello, courtesy Chris Iverson. 
The kitchen in the main home. Photo by Matt Iverson, courtesy Chris Iverson. 
The primary suite. Photo by Matt Anello, courtesy Chris Iverson. 
The primary bath. Photo by Matt Anello, courtesy Chris Iverson. 
Staircase to downstairs dressing rooms. Photo by Matt Anello, courtesy Chris Iverson. 
The 900-square-foot “hers” closet. Photo by Matt Anello, courtesy Chris Iverson.
The main house: Villa del Prato
At the heart of the property, sits the four-bedroom, seven bath family home. Designed with arched windows, mahogany rafters, walnut interior finishings, imported Italian stone columns and antique, red roof tiles reclaimed from a Tuscan villa, the home features many authentic details found in Italy’s countryside homes thanks to San Francisco architect Andrew Skurman and interior designer Suzanne Tucker, both known for creating historically driven designs.
The home features an elevator, a family room with a raised stage and a 22-foot-tall great room lined with over-sized arched French doors that lead outdoors to a covered loggia.
The primary suite occupies its own wing that includes a his-and-her bathroom, a home office, private arched loggia and a spiral staircase that leads to his-and-her dressing rooms that total 1,200 square feet. The larger, 900-square-foot dressing room is designed to resemble a Chanel boutique and doubles as a “safe room” with bullet- and bomb-resistant walls.
Beyond the main home: A Pool house & an entertainment house
Beyond the main house is the two-bedroom pool house that features a fully equipped gym,a great room, a laundry room and a gourmet kitchen.
On the third lot is the two-level entertainment house, which is large enough to accommodate a ballroom on the main level, as well as a 10,000-bottle wine cellar below.
Other notable property amenities include four separate multi-car garages (with two tall enough for lift parking), a secondary panic room located within the main home’s “safe room,” and separate irrigation wells, power generators and mechanical systems infrastructure for each structure. There’s also hospital-grade HEPA filters for year-round clean air.
A price tag 16x town’s median home value
At $65 million, the property’s asking price is about 16 times the town’s median home value of $4.02 million, according to August real estate data from Zillow.
According to Iverson, the property is currently the second-most expensive listing on the Midpeninsula: A house in Hillsborough built by the same architect and designer is on the market for $115 million.
Just up the Peninsula, the historic Green Gables estate in Woodside sold on Sept. 3 for $85 million – reportedly the priciest sale in the Bay Area so far this year.
