A storied town founded by California’s most distinguished 19th-century industrialists, Hillsborough possesses a glorious legacy of prominent living as well as a distinguished link to the colorful history of San Francisco dating back to the California Gold Rush. Hillsborough flourished to become a prestigious country estate and destination of San Francisco’s significant wealth during the early days.

Nothing compares to Hillsborough’s heritage, prominence, and stature. Some of its sights are a testament to its history and vibrant culture. The Carolands, also known as “The Chateau” is a California landmark and is listed on the National Registry of Historic Places. Guests can take a tour of this 1915 estate and see firsthand a fine example of French Classical architecture in America.

The pleasant town still continues to represent affluence and exclusivity today, but with the charm and laidback appeal of a suburban neighborhood. And while 20th-century mega mansions designed by famed architects such as Angus McSweeney, William Wurster, Willis Polk and Gardner Dailey still remain standing, a mix of modern and traditional, but equally luxurious homes have also been constructed.

The upper landscape of Hillsborough features rolling streets and wooded neighborhoods dominated by large and private estates occupying over an acre parcel of land, while the lower Hillsborough offers just as opulent homes sitting on level lots that are closer to San Mateo and Burlingame’s downtowns. Sidewalk-free roads paint that perfect woodland picture –creating not just private country seclusion with a quiet atmosphere, but a naturally charming destination that’s more than cozy enough to call home. 

Hillsborough boasts of an esteemed blend of sophistication, security and natural beauty, ensuring a refined lifestyle that is congruous to family life and education. An acclaimed school system is another facet that sets Hillsborough apart from other towns. Top-rated schools include North, West and South Hillsborough Elementary Schools, Crocker Middle School and private schools such as Bridge School, Nueva and Crystal Springs Uplands –all offering a rich diversity of classes that emphasize integrated studies and social-emotional learning, along with an athletics program, visual and performing arts and other extra-curricular activities that pave the way toward self-discovery, growth and creative expression. 

The Hillsborough City School District consistently works in partnership with students, parents, and other community members toward the main goal of educating students in a nurturing environment, empowering each child to become a responsible and contributing participant in society.

Hillsborough Recreation is an organization that provides the community with sports and enrichment classes for both children and adults. While tennis courts abound in Hillsborough, other recreational activities can be explored to suit varying interests. Classes include golf, yoga, piano and art while summer activities revolve around writing, basketball and volleyball camps, as well as art workshops.