Visit these landmark estates and see what it was like a century ago (or more).

Filoli in Woodside is one of the most popular estates to visit on the Peninsula. (Photo courtesy Gretchine Wilson/Filoli)

Wealth and the San Francisco Peninsula (Silicon Valley) have been entwined long before the likes of Apple and Oracle. More than 100 years ago, the Peninsula had the largest collection of country estates west of the Mississippi. And, though most of the area’s large estates like Mills (Millbrae), Gables (Woodside), and La Dolphine (Hillsborough) have either been demolished, sold or parceled off, or remain in the hands of private citizens, there are several that are run and supported by nonprofits or cities, welcoming and educating visitors on the area’s history.

These estates wouldn’t have been built without massive land acquisitions, many initiated by the California Land Act in 1851. The wealthy converged on this pristine land, bought up acres and built their summer homes, traveling via the newly built railroad. Their actions amplified a divide that would only grow, mostly through generational wealth. Silver baron James C. Flood – of Flood Mansion fame – built a country estate named Linden Towers, with remnants of the estate still evident throughout the Lindenwood neighborhood of Atherton, including the brick wall along Middlefield Road. William Ralston had his country home in the Belmont canyon area, Cipriani House, enlarged to 100 rooms and hosted lavish parties. And of course there’s Leland and Jane Stanford.   

Some of that wealth (and property) were squandered, but some owners and heirs reinvested in their communities. Visit these gems and learn how they came to be and how their place in local history impacts life here today. All of these historic homes are free to visit unless otherwise noted, but donations keep them up and running.

The Johnston House off Highway 1 near downtown Half Moon Bay was built by James Johnston as a gift for his wife. (Photo courtesy San Mateo County and Silicon Valley Convention and Visitors Bureau)

James Johnston House

This historic saltbox-style New England colonial sits unassumingly in the middle of a field of wildflowers and native grasses just south of Half Moon Bay’s Main Street. You might not be able to visit it today if it was not for Malcolm and Joan Watkins, who discovered the home’s provenance during a road trip in 1962. The house, built in 1855 by Scottsman James Johnston, was a gift for his Mexican-born wife, Petra de Jara, according to docent Gail Stevens. “He wanted to build this stately type of farm and home that would be worthy of his wife, Petra,” she says. Petra came from a long line of rancheros, but even she couldn’t help Johnston with his cattle-ranching prowess. The ranch, along with the home, was foreclosed on by 1879. When the Watkins’, who were affiliated with the Smithsonian, discovered this treasure, they initiated a round of conversations that resulted in its restoration.

James Johnston House, 110 Higgins Canyon Road, Half Moon Bay; 650-726-0329. Open for visitors on the third Saturday of every month from 11 a.m. to 3 p.m. 

Sanchez Adobe, part of the San Mateo County Parks system, is a historic mission in Pacifica built in the mid-1800s. (Photo courtesy Wikimedia)

Sanchez Adobe

This historic mission, tucked into Pacifica’s San Pedro Valley, is often overlooked by locals as a great history-lesson outing, even without kids. The area’s original inhabitants, the Ohlone, passed down their knowledge of the land to the missionaries, and later, Mexican rancherias (settlements), who occupied the land. Francisco Sanchez, a prominent member of a Californio family, built the Sanchez Adobe between 1842 and 1846. As one of the oldest homes built in San Mateo County, this former residence changed hands several times. It was used as a brothel, hotel, and storage facility for artichokes, among other things. The county purchased the home in 1947, and today it serves as a living memorial to the Ohlones. The land on which this home sits is so intrinsically linked to California’s history that a visit is essential to understanding how we got here and how to lead in the future.

Sanchez Adobe; 1000 Linda Mar Blvd., Pacifica; 650-359-1462. Visiting hours are Tuesday, Wednesday and Thursday, 10 a.m. to 4 p.m.; Saturday and Sunday, 1-5 p.m. 

The Kohl Mansion is home to Mercy High School, and the mansion and grounds can be rented for private events. (Photo courtesy Wikipedia)

Kohl Mansion

Kohl Mansion, built between 1912 and 1914, was the centerpiece of a 40-acre estate owned by Charles Fredrick “Freddie” Kohl, a wealthy man who built the home in honor of his wife, Bessie. Kohl’s father was an Alaskan shipbuilder and fur trader, and his wealth was passed down to his Swarthmore-educated son. Freddie and Bessie’s charmed life was short-lived, and soon enough, the Tudor-style estate and surrounding property were sold to The Sisters of Mercy in 1924. Since then, the estate has remained part of this religious order, first as a motherhouse, and in 1932, an all-girls high school.

Besides being home to Mercy High School, the mansion and grounds can be rented for private events. It’s also the venue for Music at Kohl, so even though there are no formal tours, attending a concert affords the opportunity to poke around the house while supporting local chamber music and music education in the local schools. 

Kohl Mansion; 2715 Adeline Drive, Burlingame; 650-762-1137.

Filoli’s 16 acres of gardens are its focal point, and each season brings about a plethora of blooms from flowers, shrubs and trees. (Photo by Veronica Weber)


Filoli is, without question, the most noteworthy estate on the Peninsula. This 56-room country estate, with its 650 acres, is large enough to offer surprises with every visit. The 16 acres of formal English gardens are the focal point, and each season brings about a plethora of blooms from flowers, shrubs, and trees. Their cutting garden, an extravagance reserved for the most stately manors, fills the house with floral installations that shouldn’t be overlooked. Though the Bourns, who built the estate in 1917, were widely disparaged for their wealth and the private water utility company they owned, they are now remembered as erecting one of the area’s most beautiful gifts. Visitors can walk the grounds and explore this neo-Georgian estate daily. Check their calendar of events for programming, often included in the cost of admission ($25 for adults). For free passes, visit Discover & Go and see if your local San Mateo County library card participates in the program. 

Filoli, 86 Cañada Road, Woodside; 650-364-8300.

Elizabeth Gamble spent her life growing the gardens surrounding her family’s estate and bequeathed the home and grounds to the city of Palo Alto. (Photo courtesy @NadinePriestleyPhotography)

Gamble Garden

The stately New England and Georgian Colonial Gamble estate, built in 1902, was commissioned by Edwin Gamble, son of James Gamble (Procter & Gamble). It’s said that they moved to Palo Alto so that their three sons could attend Stanford University. Their daughter, Elizabeth F. Gamble, returned to the home after college and spent her life there, tending and growing the gardens that surround the estate. She bequeathed the home and grounds to the city of Palo Alto, and after her death, the estate was leased to the Elizabeth F. Gamble Garden Center, a nonprofit that maintains the estate and grounds.

This jewel in the center of Old Palo Alto is open every day for exploration and contemplation. The first floor of the home is currently closed until further notice. But really, it’s the gardens that are the main attraction. Several garden “rooms” provide special places to admire, like the wisteria garden that explodes with blooms during the spring. There are also numerous planting beds, tailored to different types of plants like annuals and foliage specimens. The pollinator and edible gardens are tailored to our climate, and a new watershed garden provides tips on being waterwise. 

Gamble Garden, 1431 Waverly Place, Palo Alto; 650-329-1356.

The Rengstorff House was fully restored in the 1990s and is now accessible via docent-led tour. (Photo courtesy Ashley L./Yelp)

Rengstorff House

Mountain View’s Rengstorff House is located not far from the city’s Shoreline Lake, a vast 750-acre park and recreational space that includes a lovely body of water with boating and kayaking activities. Of course, when Henry Rengstorff first settled in Mountain View, the area was strictly agricultural land. Rengstorff, who emigrated from Germany and made his fortune buying up parcels of land all over the Peninsula, built his home in 1867 on 200 acres of land that is now Shoreline Business Park. He and his wife raised seven children in the Victorian Italianate home. With almost 4,000 square feet, the home was large enough to raise a family and host other prominent members of the Peninsula at that time.

The home remained in the family until 1949 when it, along with the land, was sold off to land developers. The home was abandoned and continued to decline until the city committed to restoring it. In 1991, it was fully restored with support from The Friends of “R” House. A docent-led tour not only provides a glimpse of life on the estate, but also life in and around Mountain View’s shoreline before it became a tech hub. 

Rengstorff House, 3070 N. Shoreline Blvd., Mountain View; 650-903-6073. Temporarily closed due to rise in COVID cases as of Jan. 8.

The J. Gilbert Smith House shingle farmhouse was built in 1905 and today is part of the Los Altos History Museum. (Photo by Kevin Legnon)

J. Gilbert Smith House

This craftsman-style shingle farmhouse was built in 1905 by J. Gilbert Smith, an Oregonian carpenter who had settled on the Peninsula with his mother. The property sat in the middle of 5 acres of prime farmland, which quickly became part of the area’s famed apricot orchards. The home, which Smith himself built, is considered a Depression-era house, and when you walk through it you might recognize things like early kitchen appliances, vintage furniture, and collectibles like glassware and textiles that can be found at secondhand shops and flea markets. By the ‘50s, Smith had more than doubled his orchard’s acreage, and in 1954, he sold the land to the city of Los Altos. Smith and his wife Margaret remained in the home until Margaret’s death in 1971, at which time the city made structural improvements and began work on turning it into a place for all to visit. The house, part of the Los Altos History Museum footprint, is open Thursday-Sunday from 11 a.m. to 5 pm. Call ahead to confirm that a docent is available, which is the only way to visit the home’s interior. 

J. Gilbert Smith House, 51 S. San Antonio Road, Los Altos; 650-948-9427.

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