A peaceful enclave in the hills south of San Francisco
Hillsborough is a town of 11,000 people in the foothills of the Santa Cruz Mountains. It offers high-end homes along with peace and privacy. The area was developed as a community of country estates for prominent families, including railroad magnates. Since then, it has continued to attract the rich and famous, including Bing Crosby, William Hearst and Alden Clausen, who was head of the World Bank and Bank of America. Hillsborough and the neighboring city of Burlingame share the 26th wealthiest zip code in the United States.
Despite the prestigious zip code, Hillsborough has a down-to-earth community vibe. “In some other high-end areas, the neighbors don’t know each other. But we have a very tight-knit community that is upheld really well by an online system that binds people together. We also have fundraisers, like an annual car show and a fun run for the kids,” says Milana Ostroy, a Realtor and founder of Milana Real Estate Group who lives in Hillsborough. “We all know each other. I know every one of my neighbors — our dogs even know each other.”
The town of Hillsborough is located south of San Francisco.
Hillsborough is very residential, so locals can enjoy jogging on its wide, winding streets.
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Carolands and other historic mansions center quiet neighborhoods
Historic mansions center several Hillsborough neighborhoods and they range from relatively modest to spectacular. New homes must have a minimum of 2,500 square feet on lots of at least half an acre, but most Hillsborough homes are larger; averaging about 4,000 square feet. In the Tobin Clark Estate neighborhood on the eastern border, ranch-style and mid-century homes up to 6,000 square feet surround the Tobin Clark Tudor mansion, which was built in 1931. The Carolands neighborhood is also named for the historic estate at its center, It has homes around 14,000 square feet, and some have Beaux-Arts architectural elements such as Mansard roofs, grand entrances and bas-relief panels. The Skyfarm neighborhood is named for a 1931 mansion built for the Crocker family. In this neighborhood, stately traditional and Mediterranean revivals with over 5,000 square feet overlook the bay and hills. The median price of a home in Hillsborough is $5.5 million, and the average Hillsborough home value is 9 times the national average.
Lovely landscaping is the norm in Hillsborough.
This two story home in Hillsborough has a unique design.
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Restaurants and shops in nearby Burlingame and San Mateo
When Hillsborough was incorporated, town leaders prohibited businesses. “They were protecting what they referred to as a rural setting,” says Tim Anderson, Director of Building & Planning for Hillsborough. “That meant no post office, no gas station, no corner store, no hair salons and no pubs. Now people are comfortable keeping it residential, and it’s very quiet. With just a half dozen or so stoplights, it’s sometimes called the dark city.”
Today, Hillsborough remains residential with very little buisness in its borders, and most residents go to Burlingame or San Mateo for shopping, dining and entertainment. RASA, an Indian restaurant in Burlingame, and Pausa Bar & Cookery in San Mateo have earned recognition in the Michelin Guide. “Burlingame Avenue has become the go-to place on the Peninsula for people who want to go out but not to the City,” says Ostroy. “It has the trendy restaurants, luxury shopping, a lot of jewelry stores, coffee shops, a post office and an array of grocery store choices. There is also a farmer’s market on Thursdays and the weekend — that’s really popular in suburban life.”
Avocado Toast and 3 bees in are right next door to each other near Hillsborough.
Safeway is the one-stop shopping center for residents of Hillsborough.
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Golfing and hiking in Hillsborough and Crystal Springs areas
Hillsborough golfers have a choice of nearby courses. The Burlingame Country Club, located in central Hillsborough, was built in 1893 and has a private 18-hole golf course with views of the San Francisco Bay. The Crystal Springs Golf Course is integrated into the natural area surrounding the Crystal Springs Reservoir, west of town. Hikers are drawn to the Crystal Springs area — the Sawyer Camp Trailhead is on the southwest tip of the town. Several small parks within Hillsborough have sports facilities and playgrounds.
Burlingame Country Club in Hillsborough has many activities for club members.
Hillsborough is a popular destination for golfers due to its multiple golf courses.
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Schools are rated A-plus with Nueva School a private option
The town is served by the Hillsborough City School District, which is rated A-plus by Niche and the San Mateo Union High School District, also rated A-plus. The Nueva School is a private kindergarten through 12th grade school in Hillsborough, graded A-plus, that requires admissions testing. Crystal Springs is a private middle and high school known for sports and intimate learning. It is also graded A-plus.
The Bridge school serves students living in Hillsborough.
The sprawling campus of Hillsborough High School.
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San Francisco, Palo Alto and San Jose in reach
Interstate 280 connects Hillsborough to San Francisco, 20 miles away. Palo Alto is 20 miles south and San Jose is under 40 miles. The San Francisco International Airport is 6 miles from Hillsborough. The nearest hospital, the Mills Peninsula Medical Center, is under 3 miles away. There is also a BART station in nearby Millbrae.
Hillsborough’s ADUs, wildfires and crime rates
The State of California has expanded requirements for affordable housing, which impacts Hillsborough because of its low-density nature. The Town has relaxed restrictions on Accessory Dwelling Units (ADUs) to encourage homeowners to build them, and the town may rezone two parcels of land for high-density units to meet state requirements. Hillsborough is at risk for wildfires, and the town has taken steps to mitigate the risks by encouraging the establishment of defensible spaces and promoting evacuation preparedness. Property crime in Hillsborough decreased 10% from 2018 to 2023, according to FBI data. Violent crime nearly doubled from 2018 to 2023, but the number of incidents was very low: 9 in 2018 and 17 in 2023.
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Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
