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The Midpeninsula has no shortage of seriously unique homes. From a 1920s-era Birge Clark original Mediterranean villa with a mosaic pool inspired by Hearst Castle to a custom-built home with an indoor ice rink and pizza room, 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 or recently sold.
$2.9M
Iconic ‘Grateful Dead House’
1,008 square feet, 2 bedrooms, garage studio
Palo Alto
Sold
This 106-year-old, wood-shingled Palo Alto bungalow is where members of legendary rock band the Grateful Dead chose their iconic name
Located in Palo Alto’s Professorville neighborhood, the two-bedroom home is considered a significant place of importance in Grateful Dead history. It was on the front porch where lead guitarist and vocalist Jerry Garcia reportedly landed on the group’s name in November 1965.
As the story goes, Phil Lesh invited his bandmates from the Warlocks — Garcia, Bob Weir and Bill Kreutzmann — over to the home, which he was renting at the time, to find a new name after discovering another band also was called the Warlocks.
Garcia was flipping through a dictionary when he randomly found the entry “Grateful Dead” — and the rest is history.
The home was listed for $2.6 million in June and sold for $2.9 million in July.
$14.5M
A Birge Clark original
7 fireplaces, 900-bottle wine cellar, mosaic pool
Palo Alto
On the market
With its red-tiled roof, stucco walls, arches and wrought iron details, this 1927-era villa in Palo Alto’s Crescent Park neighborhood has many of the iconic features one would expect in a home designed by Palo Alto architect Birge Clark, whose work defined the burgeoning city’s Early California style.
The three-level Mediterranean-inspired villa underwent a three-year remodel after the owners purchased the property in 2005. DeMattei Construction was careful to preserve the character of the home by incorporating features like richly hued hardwood floors and towering arched windows into the remodel, according to the listing.
The home sits on a half acre and features seven fireplaces, an elevator, five en suite bedrooms, a separate one-bedroom guest house, a library, wine storage for approximately 900 bottles, a recreation room with a bar, and a pool with glass mosaics inspired by Hearst Castle.
The home has been listed on and off the market for the past 11 years. It was initially listed on the market for $12.8 million in 2013, according to Zillow. It was most recently listed on the market for $14.5 million in May.
$19.9M
Historic ranch
14 acres, 1,500 fruit trees, 15-car garage
Portola Valley
Sale pending
Since the 1890s, generations of families have enjoyed locally grown fruit from this 14-acre working orchard known as Jelich Ranch. It’s become a notable landmark in the heart of Portola Valley.
The Jelich family operated a fruit stand at the site for more than a century before local residents Phil and Cindie White bought the neglected property in 2000 and in keeping with the spirit of the old ranch decided to revive it. Today, the historic ranch is certified organic, and the apples, pears, peaches, plums, nectarines, figs and other fruit from its 1,500 or so trees are sold by local grocers like Bianchini’s and Roberts.
The original 1920s farmhouse has been restored, from all-new push-button light switches, cord-and-pull windows, cabinets with traditional saw-tooth shelving to beadboard paneled ceilings and Douglas fir floors, according to the listing. The property also includes a restored guesthouse, a wellness center with a sauna and meditation garden, a separate two-room art studio, an agricultural barn, a refurbished tank house currently used as a playhouse and an expansive garage capable of housing up to 15 cars. The owners were honored earlier this year by the Portola Valley Town Council for their restoration of the ranch.
The property was originally listed on the market in October 2023 for $19.9 million. It was listed as “pending” at the start of September. This is only the second time the ranch has changed hands.
$35M
20-room home with indoor hockey rink
4 stories, 21,082 square feet, 13.35 acres
Palo Alto
Sold
This 21,082-square-foot custom-built home in Palo Alto Hills made headlines in 2018 with its record-breaking price tag of nearly $100 million. After being on and off the market for more than five years – and re-listed for $53.9 million in 2023 – the home sold for $35 million in July.
Located on 13.35 acres, the home was custom-built for Sun Microsystems co-founder Scott McNealy, his wife and their four sons, who lived on the property for more than a decade.
The four-story, 20-room home includes a pizza room, a poker room, a spa with a sauna and massage table, a disco, a full gym with a climbing wall; an indoor basketball court, a wine cellar, a billiards room, a theater and a 110 yard golf practice area with two putting greens. There’s also a 7,000-square-foot multi-purpose indoor ice rink/tennis court with its own locker room. And for overnight visitors, there’s a one-bedroom detached guest house.
$19.9M
Classic manor by renowned modernist architect
11,745 square feet, 1.5 acres, guest apartment
Woodside
On the market
From its slate tile roof and leaded glass windows to its green marble foyer and sculpted gardens, this expansive English-style country manor is impressive inside and out – and so is its 90-year history.
Renowned modernist architect Gardner Dailey designed this home for his wife’s family in 1934 prior to embracing modernism and earning international fame for breaking new ground with his residential designs. He often is credited for introducing modernist architecture to Northern California.
In 1983, Apple’s newly hired CEO, John Sculley, purchased the property, where he lived for seven years before selling it to Samuel Maslak, the co-founder of pioneering ultrasound company Acuson Corporation, for $3.4 million, according to various reports.
Under Maslak’s tenure, the 1.5-acre property was meticulously renovated and updated for several years, while care was taken to maintain the home’s early heritage and original charm, according to the Robb Report.
The 11,745-square-foot home features six bedrooms, seven full bathrooms, a ballroom-sized living room with a coffered ceiling, a dining room with a wall of glass, and a library and adjoining sitting room with a bar that opens up to the pool. An exercise room is just off the library, where expansive windows and glass doors open to a terrace with sweeping views of the San Francisco Bay, Mount Diablo and the adjacent Menlo Country Golf club. On the main level is a one-bedroom guest suite originally designed as the personal quarters for Dailey and his wife, according to the listing. There also is an apartment that can be accessed from a private outside entrance.
The home was reportedly available off-market for $22.5 million last April. It is now listed for $19.9 million.
$5.5M
Streamline Moderne home
Curved and fluted walls, flat roof line, chevron patterns
Palo Alto
Sold
This Art Deco throwback from the 1930s is a rarity in Palo Alto’s residential neighborhoods.
Built in 1937 by Palo Alto architect and builder William F. Klay, the home is considered a pristine example of Streamline Moderne — a subcategory of the Art Deco style that was considered less flashy than its predecessor.
The style emphasizes rounded corners, long horizontal lines, an abundance of chrome accents, porthole-shaped windows and other aerodynamic design elements found in cars, planes and ships. Due to the style’s futuristic curves and transportation themes, however, its use in single-family homes was short-lived as it seemed better-suited for gas stations and train depots.
Although a second-story addition was added to the home in the 1950s and other upgrades have been made through the years, its original Streamline Moderne details remain intact, according to the historic preservation group Palo Alto Stanford Heritage, which describes the home as a “fine example of an important style which is relatively rare.”
The home is listed in the city’s historic inventory as a “major building of regional importance” and also has been recognized by the Art Deco Society of California.
The property was listed on the market for $6.3 million in September 2023, and sold in April for $5.5 million.
$33.3M
Mini Tuscan mansion
3 levels, 12,000 square feet, 1.55 acres
Atherton
On the market
For nearly two decades, this mini Tuscan mansion in West Atherton served as the primary residence of Marc Andreessen, co-founder of venture-capital firm Andreessen Horowitz, and his wife, Laura Arrillaga-Andreessen, daughter of Silicon Valley philanthropist and developer John Arrillaga and founder of the Laura Arrillaga-Andreessen Foundation, according to the Robb Report.
Built in 1995, the 12,200-square-foot home underwent a “total transformation” after the couple purchased it in 2007, according to the sale listing.
The property is designed “to host significant personal, professional and philanthropic events,” according to the listing. The main home features multiple living rooms, including one with a cream-hued fireplace and floor-to-ceiling French doors leading to a private balcony and another with soundproof suede walls. The home also has been outfitted with two kitchens “to facilitate seamless catering or a personal chef.” One bay of the four-car garage has been converted into a versatile office or caterer’s space, complete with appliances and “ample space for event management or a property manager’s daily operations.”
The three-level home also features five-bedrooms, seven-baths, an elevator, home theater, gym, seven fireplaces and a family room that opens to a covered terrace sporting a built-in barbecue set on a 1.55-acre lot. The property also comes with a one-bedroom guest house, a detached studio and its own well for irrigation.
The home was listed on the market in March for $33.3 million, or $2,683 per square foot.
$4 million
1906 Victorian
Fish scale shingles, cross-gable roof, full-width dormers
Palo Alto
On the market
This Victorian is an early example of a single-family residence built in Palo Alto’s original street grid 118 years ago. The 1906-era home, which was used as a boarding house for students during its early days, is considered historically significant for its unique design, which combines elements of the Queen Anne, Colonial Revival and bungalow styles.
The fish scale shingles at the home’s upper gables reflect the elaborate features – decorative trim, towers and turrets – often associated with Queen Anne residences, which began popping up in Palo Alto’s earliest neighborhoods near the turn of the 20th century after the opening of Stanford University, when young professors moved to the area and popularized the style. The home’s wide, covered front porch with supporting columns and full-width dormers are elements found in the bungalow style, known for its cozy and inviting appearance.
The gable roof features intersecting rooflines, or cross-gables, that can be associated with the Colonial Revival style.
In 2023, the city’s Historic Resources Board recommended the home be included in its historical inventory. The historic preservation group Palo Alto Stanford Heritage also recognized the home’s significance by marking its 100th year with a centennial plaque.
Located in Palo Alto’s Downtown North neighborhood, the 2,735-square-foot home features six-bedrooms and three baths and is the perfect opportunity for those who appreciate old world charm and want to “bring a renewed spirit” to an old home, according to the listing.
The home was listed on the market in August for $4 million.
