A picturesque town with exclusive estates and dramatic views of San Francisco Bay
Hillsborough is perhaps the most exclusive community in the Peninsula. City law prohibits commercial businesses, and building codes dictate that houses have to be at least 2,500-square-feet on no less than half-acre lots. The average home in Hillsborough is actually twice that size. Townhouses, apartments, and condominiums are also prohibited within city limits. It has always been a prestigious place where only big, lavish estates were allowed to be built.
A prime example is the Carolands. Built in 1916, this Beaux-Arts mansion was inspired by the architecture of Louis XIV and has 98 rooms and landscaped gardens covering over five acres of land. Notable residents of Hillsborough have included singer Bing Crosby, William Randolph Hearst, and George Tupou V, the former King of Tonga.
Many of the city’s original estates have been subdivided to make way for contemporary homes and remodels, especially in the Carolands and Country Club Manor neighborhoods. You can find older Tudor and Mediterranean-style homes in Hillsborough Heights and other pre-war architecture in Hillsborough Oaks. The Parrot Drive area and Hillsborough Hills feature hideaway homes with views of San Francisco Bay. Closest to downtown, the Brewer and Upland area has more contemporary homes.
With a prestigious lifestyle, Hillsborough is an incredibly active and tight-knit community. Residents know each other. They volunteer and participate in local events and politics. The entire town usually comes out to local festivals and celebrations. Because there’s no commercial activity, Hillsborough has a serene and laid-back atmosphere.
There are no restaurants in Hillsborough, but downtown Burlingame is less than a 10-minute drive, where there’s a grocery store, an Apple Store, nightlife, and plenty of eateries. Flights Restaurant serves American comfort food in shareable flights. Stella Alpina Osteria serves northern Italian dishes. Limon is a popular Peruvian restaurant.
The Vinyl Room is a weekend lounge with dancing and DJs. You can also check out the Burlingame Fresh Market on Thursdays and Sundays or the College of San Mateo Farmers' Market on Saturdays.
Neighborhood parks include Vista Park, which has a playground, a basketball court, and picnic tables. Crossroads Park and Centennial Park both have walking trails and gardens. The Sawyer Camp Trail in San Mateo and Mills Canyon Park in Burlingame offer miles of trails for more avid hikers.
Hillsborough organizes events every year. The Memorial Day Parade and Carnival features local musicians and a parade that starts from the Hillsborough Town Hall. The Concours d’Elegance car show has been a town tradition since 1956. Every summer, over 200 rare collector cars are displayed and judged on their design and condition. There’s also a car race and the Tour d’Elegance, where participating cars drive down scenic Bay area roads.
Crystal Springs Golf Course has an 18-hole championship golf course with beautiful views of the Crystal Springs Reservoir and wildlife refuge just a few miles away. For a private, members-only golf course, the Peninsula Golf and Country Club in San Mateo is a 10-minute drive.
Hillsborough is served by the Hillsborough City School District.
Together with his wife and son, the Buljan Group has grown as a commanding force in the local real estate realm over the years selling every major landmark property in the community.
