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The Midpeninsula has no shortage of some seriously unique homes. From a hillside home built from a cluster of towering redwood rain barrels to a 74-acre compound with its own Roman-style reflecting pool the size of a football field, these one-of-a-kind properties – whether because of their price, unusual design or history – are extravagant even for Silicon Valley. We’ve compiled a list of some of these not-so-ordinary properties that are on the market right now or recently sold.
The Fleishhacker family’s historic Green Gables estate in Woodside was relisted on the market in January with a $25 million price reduction. Photo by Magali Gauthier. 
The 74-acre Green Gables estate includes a Roman-style reflecting pool the size of a football field. Photo by Magali Gauthier. 
The Green Gables estate has been owned by about five generations of the Fleishhacker family. Photo by Magali Gauthier. 
Green Gables’ English country-style main house and gardens were designed by brothers Charles Sumner Greene and Henry Mather Greene, better known as Greene and Greene. Photo by Magali Gauthier.
$110M
Historic family compound
7 residences, 3 swimming pools, 74 acres
Woodside
On the market
Most high-end properties on the Midpeninsula market have something special that sets them apart, whether it’s acreage, unusual amenities or striking architectural features. But what about a property with 74 acres, seven houses, three swimming pools, extensive gardens, its own reservoir and a Roman-style reflecting pool the size of a football field — not to mention that the main house was designed by legendary architects? That’s all unique to Woodside’s Green Gables estate.
The English country-style main house and gardens were designed by brothers Charles Sumner Greene and Henry Mather Greene, better known as Greene and Greene, celebrated architects of the Arts and Crafts movement of the 19th and early 20th centuries.
They built the home in 1911 for the Fleishhacker family, who have owned the compound for five generations.
The historic property was officially listed for sale in February 2021 for $135 million. The price was reduced to $125 million last year. It was relisted on the market on Jan. 4 for $110 million.
$40M
Spec home
6.68 acres, 11,185-sq.-ft. home with elevator, rooftop deck
Portola Valley
On the market
Built in 2023, this spec home was designed for the ultra-luxury market. One might say the home has it all: privacy, a 360-degree view of the San Francisco Bay and coastal hills, a theater, a recreation room with its own bar, an infinity pool, a wine cellar and a separate guest house.
The home features seven bedrooms, nine bathrooms and 11,185 square feet of living space that spans three levels equipped with an elevator. Disappearing glass walls open up the home to seamless indoor-outdoor living spaces – and let’s not forget about the rooftop deck.
YLCL Investments LLC bought the property for just under $6.9 million in 2016, according to the Real Deal, and worked in collaboration with architectural firm Swatt-Miers on the project, which took about seven years to complete.
The property was initially listed on the market for $45 million in April 2023. At the time, it was believed to be the priciest listing in town history. The property was relisted for $40 million on Feb. 8.
The “Ruth Stern” house and the two–bedroom Spanish-style cottage on the adjacent lot that iconic Palo Alto architect built for the Stern family both reportedly sold in separate transactions in early March. Photo courtesy Palo Alto Stanford Heritage. 
Lucie Stern commissioned architect Birge Clark to build this modest two–bedroom Spanish-style cottage for her gardener and his wife, a registered nurse who cared for Ruth Stern. Photo courtesy Palo Alto Stanford Heritage.
$35.28M
Side-by-side matching homes
2 lots, 2 Spanish colonial revival residences by iconic architect Birge Clark
Palo Alto
Sold
These two adjacent properties in Old Palo Alto bring together the city’s renowned tech culture and early history. Iconic Palo Alto architect Birge Clark, whose red-tiled roofs, stucco walls, arches and wrought iron details defined the burgeoning city’s early streetscapes, built the homes in 1932 and 1935 for Levi Strauss heir Lucie Stern.
Stern commissioned Clark to build the 4,721-square-foot Spanish colonial revival home alongside her private residence (also built by Clark) so she could live next door to her disabled daughter, Ruth. On the other side of the home, Stern had Clark build the modest two–bedroom Spanish-style cottage for her gardener and his wife, a registered nurse who cared for Ruth Stern.
Fast-forward to the mid-2000s: The cottage and Ruth Stern’s adjoining home are acquired by another family. Ruth Porat, president and chief investment officer at Google, and her husband, Anthony Paduano purchase the homes. The $30-million price tag for Ruth Stern’s residence made history in Palo Alto as the city’s biggest-ever home purchase at the time.
In early March, SiliconValley.com reported that Porat and Paduano had allegedly sold the two houses in separate transactions for a combined $35.28 million. The historic home built for Ruth Stern sold for $30.75 million, according to data from MLSListings. The gardener’s cottage sold for $4.53 million, according to the listing on Zillow.
$30M
Vacant lot
2.5 flat acres
Atherton
On the market
This property is flat, vacant and a rare opportunity to build not one, but two, homes on a clean canvas in West Atherton. The owner in 2014 subdivided the property into two parcels to allow for the construction of two residences, according to town documents. One parcel is 1.36 acres, the other is 1.19 acres. A 1,980-square-foot two-bedroom, two-bath home built in 1928 formerly occupied the site.
The two parcels were listed for sale together on Feb. 7 for $30 million.
$19M
Personal vineyard
41 acres, wine cellar, well-being center
Portola Valley
On the market
Completed in 2006, this 41-acre estate sits on a hillside surrounded by a private vineyard overlooking the San Francisco Bay. The 14,500-square-foot home features six bedrooms and 11 baths and a red-tile roof and stucco walls reminiscent of a Tuscan villa. The property also includes a wine cellar, home theater and a well-being center with a spa, steam room and sauna.
The property was originally listed on the market in July 2020 for $22 million. It was relisted for $19 million on July 19, 2022.
$15.5M
The Gap founders’ summer retreat
2 acres, Tudor-style home, guest house
Atherton
Sold
For nearly six decades, the property at 178 Atherton Ave. was used as the summer retreat of the Fisher family, founders of The Gap retail and clothing chain. Doris and Don Fisher purchased the estate’s first parcel for $211,000 at a probate sale in 1975 and kept adding to the family compound over the years, according to Mansion Global.
The estate, accessed by four gated entrances, included 8 acres with two homes, a guest house, a pool and pool house, a tennis court, multiple wells for irrigation and an extensive sculpture garden where the family displayed its extensive art collection along manicured walking paths.
The entire 8-acre property was listed for sale in September 2021 for $100 million. At the time, it was the most expensive listing in the city and among the 10-largest properties in Atherton, Forbes reported.
The estate comprises three separate parcels.
The property’s main home, pool, pool house and tennis court are located on a 4-acre parcel, which is listed as off market, according to MLSListings.com.
The sculpture garden, which spans 2 acres, is located on a second parcel and also is listed as off market, according to MLSListings.com.
The 2-acre parcel that sold on Jan. 31 for $15.5 million, includes a 4,105-square-foot Tudor-style home built in 1939, as well as a one-bedroom guest house.
The backyard of Joseph Eichler’s personal home that he custom-built in 1951 is shown here. Photo by David Eichler, courtesy The Boyenga Team. 
Eichler and his family lived in the Atherton home for 14 years from 1951 to 1965. Photo courtesy the Boyenga Team. 
Joseph Eichler customized every room in his Atherton home with built-in cabinetry. Photo courtesy The Boyenga Team. 
Every room in this Atherton Eichler features custom-built cabinetry and storage. Photo courtesy the Boyenga Team. 
An aerial view of Joseph Eichler’s former personal home is shown here. Photo courtesy The Boyenga Team. 
The front of Joseph Eichler’s former personal residence is shown here. Photo by David Eichler, courtesy The Boyenga Team.
$6.3M
Joseph Eichler’s personal ‘Eichler’
0.9 acre, 3,700-sq.-ft. residence, V-shape floor plan
Atherton
On the market
This home isn’t your typical Eicher. This is Joseph Eichler’s own custom-built “Eichler” that he called home for more than a decade. Built in 1951, the midcentury modern residence is considered among the most important homes of the housing legend’s career. This was his first custom-built home working with noted architects Robert Anshen and Steve Allen, who went on to become the original designers of Eichler homes. It set the groundwork for what would evolve into the California modern post-and-beam homes known as “Eichlers.”
The home features a unique V-shape floor plan with five bedrooms that open onto a landscaped yard with a swimming pool. Every room has custom-built cabinetry and storage.
The home was listed for sale on March 18 for $6.3 million. This is only the second time the home has been listed for sale.
$5.075M
A house built from water barrels
1.01 acres, 2,660-sq.-ft. redwood residence, circular walls
Woodside
Sold
Designed to mimic the surrounding redwood forest, this one-of-a-kind home features four enormous round redwood water barrels that stand two stories tall as its cornerstones. Aptly known as the “barrel house,” the home was built in 1973 and designed by architect Sidney Hoover, a Palo Alto native and Stanford University graduate influenced by Frank Lloyd Wright. The two-story home has three bedrooms, 2.5 baths and a guest house. Each bedroom is located in its own barrel with circular walls, according to the sales listing.
Views of the surrounding trees can be seen through large windows and skylights located throughout the house. From the exterior, the home’s cluster of circular shapes and redwood siding blend with the property’s forest setting.
Hoover, who helped design many local landmark buildings, including the Davies Symphony Hall in San Francisco and the Hyatt Hotel Union Square, lived in the home for two years.
The property was listed in August 2023 for $5.295 million. It sold on Oct. 17, 2023, for $5.075 million.
Thanks for the reminder about Green Gables, that modest $110,000,000 domicile where poor impoverished Elizabeth Holmes lived during her trial while claiming she couldn’t afford to compensate any of her victims.
What was the monthly rent there again?