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The Midpeninsula has no shortage of seriously unique homes. From a 162-acre ranch with its own lake and landing strip in Woodside to a custom-built home with five kitchens, a movie theater and a glass saltwater pool, these one-of-a-kind properties – whether because of their price, unusual design or history – are notable even for Silicon Valley. We’ve compiled a list of some of these not-so-ordinary properties that are on the market right now.
$12 million
Historic family ranch with ocean views
162 acres, private lake, air strip, barn
Woodside
On the market
This 162-acre property in the Santa Cruz Mountains was once part of the ranch where California’s oldest retail nursery specializing in native plants and ferns was located. Gerda Isenberg, a pioneer in the native plant movement, founded the Yerba Buena Nursery on a portion of her family’s 3,000-acre cattle ranch in 1960 to recognize the landscape value of native plants.
According to the nursery’s website, “As she rode her horse through the ranch and nearby countryside, she would collect plants in her saddlebags to see if she could make them grow.” This was the start of Yerba Buena Nursery, where she planted a demonstration garden in her yard and would educate the public about native plants. Many of the plants she propagated on the property are now endangered or extinct in the wild.
After Isenberg retired at age 94, new owners took over the nursery and relocated it to Half Moon Bay, where it is still in operation. The Woodside property that Isenberg called home, however, has remained in her family for almost a century.
The property includes a 4,230-square-foot country home with views of the ocean, a barn, workshop, lake for swimming and fishing, and an unofficial, but well-used air strip, according to the sales listing.
The two-story home, built by the family in 1983, includes four bedrooms, 3 1/2 baths, a library, a kitchen with views of the garden, and a formal dining room that looks out the back to the lake area. The living room features high wood ceilings with rustic beams, a stone fireplace and large windows to take in the surrounding view. The handcrafted doors and windows were hewn from locally sourced wood.
In the sales listing, the property is described as a ranch “right out of an old Western movie.”
$3.48 million
Fire-resistant, green tech home
1,901 square feet, all-electric, steel frame
Palo Alto
Sale pending
This all-electric green tech home in Palo Alto made headlines when it hit the market last September with its steel frame construction, fire-resistant paneling, certified greywater system and Tesla solar roof and powerwalls that provide renewable energy as needed, as well as a host of other innovative technologies.
Nearly every inch of this 1,901-square-foot home was engineered to be sustainable and conserve energy: It is designed to produce as much energy as it consumes.
Mohan Mahal, owner of SIDCO (Sustainable Innovate Design and Construction) who built the four-bedroom, three-bath home in 2023, has said he hopes to set the standard for how other passive homes are built.
Rather than lumber, the home was constructed with a Bone Structure steel frame and wrapped with Structurally Insulated Panels (SIPs) built with fire-resistant magnesium oxide board (MgO) and foam-core insulation. The home has been sealed to preserve fresh air and minimize dust, and water from the showers and laundry gets collected into a tank and filtered outside for irrigation.
The all-electric home is equipped with a solar roof and powerwalls that can collect and store enough power to last for days during outages. A heat pump provides radiant heating and cooling, and a SPAN smart electrical panel gives homeowners the ability to monitor their electricity usage in real-time and control individual circuits.
Tuscan-inspired villa. Photo courtesy Steve Lessard/Compass. 
Tuscan-inspired villa. Photo courtesy Steve Lessard/Compass. 
Tuscan-inspired villa. Photo courtesy Steve Lessard/Compass. 
Tuscan-inspired villa. Photo courtesy Steve Lessard/Compass. 
Tuscan-inspired villa. Photo courtesy Steve Lessard/Compass.
$72 million
Most-expensive U.S. listing at one time
3 acres, two homes, glass-enclosed wine room, 60-foot pool
Woodside
On the market
This Tuscan-inspired property was the most-expensive home in the United States listed for sale on Realtor.com when it hit the market for $72 million last September.
Built in 2023, the Woodside estate features design details and other amenities that are over-the-top even for the neighborhood surrounding “Billionaire’s Row” (Mountain Home Road), where the property is located.
From the home’s red-tiled rooftops and stone facade to its marble staircase with hand-forged railing, Venetian plaster walls, doors and windows imported from Italy and chandeliers from Spain, the design is reminiscent of an authentic Italian villa on a Tuscan hillside.
Taylor Lombardo Architects, a firm that specializes in luxury residential and winery design, built the estate. This is the same firm that rebuilt Napa’s Signarello Estate winery with a virtually fireproof steel, concrete and glass state-of-the-art building set inside a specially dug cave after the original wooden structure burned to the ground in the 2017 wildfires.
The 3-acre property in Woodside comes with 9,000 square feet of living space: A 7,500-square-foot main house with five bedrooms, and 5 1/2 baths and a matching 1,500-square-foot guest house with one-bedroom, two baths and a full kitchen that surround a 160-foot pool lined with rows of fountain sprays cascading into the water.
The main home has a wraparound loggia with a gas-log fireplace off the great room, and beneath the staircase is a glass-enclosed, wine cellar.
The property also features a tennis court, spa and extensive grounds with a vast lawn area and a meadow.
$4.9 million
1897-era house with 6 apartments
2,196 square feet, 6 units, 1 bloc from University Avenue
Palo Alto
On the market
Built as a single-family residence in 1897, this two-story apartment building at 405 Kipling St. in Palo Alto’s Downtown North neighborhood provides a glimpse of what the residential streetscape looked like when the area was first developed. The property, listed on the city’s Historic Building Inventory, is located within Palo Alto’s original street grid just a block off University Avenue and is part of several 19th-century historic neighborhood buildings (referred to as the “405 Kipling Group”) that still stand along the 400 block of Kipling Street.
The home features a Victorian-style gable with decorative fishscale shingles and a “classically detailed” verandah that wraps around the front of the building.
Architect H.L. Upham, who designed many buildings in Palo Alto during the 1890s and early 1900s built the home for Norris Smith, a forty-niner looking to strike it rich during California’s 1849 Gold Rush before settling in Palo Alto in 1897, according to the nonprofit preservation group Palo Alto Stanford Heritage (PAST).
Through the decades, the home has been used as both a single-family and multi-family residence, as well as for commercial uses. It was home to a rare books store in the 1950s and a books and records shop in the 1980s. The neighborhood is currently zoned for grandfathered office space, mixed-use and residential.
The 2,196-square-foot home is now a multi-family residence with six apartments (a mix of one-bedroom and studio units), according to the sales listing.
$55 million
‘Resort-style’ spec house
15,435 sq. ft., 5 kitchens, movie theater, gym
Atherton
On the market
From its five kitchens and primary bedroom with a kitchenette and his-and-her bathrooms to the movie theater, tennis court and saltwater pool with a glass wall and adjoining cabana/guest house, gym and lounge complete with a bar and pool table, this 15,435-square-foot newly built spec home in Atherton was designed to replicate resort living.
The amenities don’t stop there: The three-level home, located on 1.42 acres, is surrounded by floor-to-ceiling glass walls that open up for indoor-outdoor entertaining and comes with an elevator, a catering kitchen, a 500-bottle wine cellar, artisan hand-painted doors and a 30-foot Bocci chandelier that extends multiple stories, according to the listing. There’s also a spa that includes a sauna and steam room.
Designed and built by the seller, this property took about five years to complete. The spec home made headlines in 2023 when Zoom CEO and founder Eric Yuan, who agreed to purchase the property for $37 million in 2021, backed out of the deal and reportedly sued the developer over construction costs and timelines that allegedly went far beyond initial estimates, the Real Deal reported in June 2024.
