Hillsborough
Hillsborough has been home to the elite ever since the land was purchased by William Davis Merry Howard (of Hillsborough, New Hampshire) in 1846. It is just 17 miles south of San Francisco, making it an easy commute—even back in the 19th century. Wealthy San Francisco businessmen moved here because they could enjoy country living and still work in the city when needed.
The area became an incorporated town of San Mateo County in 1910. From then until 1938, the population grew from 750 to 2,500. It was around this time that the massive estates began to be subdivided into smaller lots. Today, the town has a population of more than 11,000 and remains a popular choice for people who want to relocate out of San Francisco and into an elite suburb.
Hillsborough and Atherton are often grouped together as the Peninsula’s most affluent real estate but there are some differences between the two. Atherton is mostly flat with larger lots of a mandated one-acre minimum, affording residents extreme privacy. Hillsborough’s minimum is 0.5 acres which means some smaller lots, but still spacious and all single-family homes. And what you may give up in privacy, you make up for in community and are more likely to know your neighbors. There are more hills here, particularly as you travel west away from El Camino, which gives the town a nature vibe and can mean great views for some homeowners. There is less construction happening here than a lot of the Peninsula, which only adds to the quiet peaceful neighborhood feel.
This is a strictly residential community—though neighboring Burlingame has a luxe downtown area where Hillsborough residents can conveniently shop and dine. The town borders the stretch of Interstate 280 from San Mateo to Millbrae, making the rest of the Bay Area within easy reach. The Burlingame Country Club is one of the town’s only non-residential exceptions with golf, tennis, croquet, a pool and even trout fishing.
Hillsborough High School Seminole Heights / Photo by: Tommycane at Wikimedia Commons
Hillsborough also has its own school district, which is a unique offering for a small affluent town like this. The first Hillsborough school was a single classroom built in 1911 for just six students. Now, there are three elementary schools and Crocker Middle School. Schools are highly ranked with test scores putting the district in the state’s top 1%. Students funnel into the San Mateo Union High School District for high school.
Hillsborough is home to some incredible homes, many rich in history and built by famed architects. Here are three highlights:
This is one of the largest properties in the country and listed on the National Registry of Historic Places. It was built in 1915 for Harriett Pullman Carolan, heiress to the Pullman railway. It is a 98-room French chateau, originally constructed on a 554-acre site with tea house, orangerie and tempietto. The property was subdivided over time and the house began to deteriorate. Fortunately, it’s been restored in recent decades and donated in 2012 to the Carolands Foundations, a non-profit that will continue to preserve the property.
The Carolands, Hillsborough / Photo by: Sanfranman59 / CC BY-SA 3.0
Western White House
The Hearst family (media magnates) left their mark on Hillsborough with the Western White House with this 27,000 square foot, 22-room mansion. It was commissioned by George Hearst and redesigned by Julia Morgan, the same famed architect that built Hearst Castle on California’s central coast. It is meant to intentionally look like the White House with Georgian Colonial architecture, cherry blossom trees and a library that resembles the Oval Office. Prior to Hearst, the home was owned by the Crocker family who bought it from William Henry Howard (son of Hillsborough’s founding father).
Flinstone House
This is arguably the most unique, well-known (and at times controversial) home in all of Hillsborough. It was designed by William Nicholson and built in 1976 with domed ceilings, round rooms and a master bathroom with a floor made of rocks. Over time, it was nicknamed the Flintstone House, an identity recent homeowners embraced, adding large steel sculptures of dinosaurs, a woolly mammoth and Fred Flinstone to the yard, and painting it a deep orange with a purple dome. Some neighbors labeled it a “public nuisance” and even filed a lawsuit. You can catch a good view of the home driving down Interstate 280.