Rancho Feliz

Crystal Springs Regional Trail is a county park located between San Bruno to the north and Woodside to the south. The park comprises three main trails: Crystal Springs Trail on the south, Sawyer Camp Trail in the middle, and San Andreas Trail in the northern section, which run along the eastern shore of San Andreas Lake in San Mateo County. Settled thousands of years ago by the Shalshone Indians, the Crystal Springs Reservoir (separate from San Andreas Lake to the north) is currently part of the City of San Francisco's Hetch Hetchy Reservoir water system. Crystal Springs reservoir is long and narrow because it lies atop the San Andreas Fault. The famous fault runs right through the Crystal Springs Reservoir. Satellite images and maps show the long narrow San Andreas rift continuing north of San Francisco in Tomales Bay, in Point Reyes National Seashore in a straight line. The Crystal Springs Dam survived both the 1906 earthquake and the 1989 Loma Prieta quake with no damage whatsoever, according to the U.S. Geological Survey.

Carolands Chateau is a 46,050-square-foot (4,278 m2), 4.5 floor, 98 room mansion on 5.83 acres (2.36 ha) in Hillsborough, California. An example of American Renaissance and Beaux-Arts design, the building is a California Historical Landmark and is listed on the National Register of Historic Places. Carolands is one of the last of the houses built during the Gilded Age, a period of great mansion-building that included famous houses of the Vanderbilt family, such as Marble House, Biltmore Estate and The Breakers, and stately California houses such as Filoli and the Huntington family's mansions.

Crystal Springs Reservoir is a pair of artificial lakes located in the northern Santa Cruz Mountains of San Mateo County, California situated in the rift valley created by the San Andreas Fault just to the west of the cities of San Mateo and Hillsborough, and I-280. The lakes are part of the San Mateo Creek watershed.

Crystal Springs Dam is a gravity dam constructed across the San Mateo Creek which is in San Mateo County, California. It impounds water to form the Lower Crystal Springs Reservoir which sits atop the San Andreas Fault in a rift valley created by the fault. The dam itself is located about 300 yards (273 meters) east of the fault. It was among the first concrete gravity dams built in the western United States. Skyline Boulevard runs over the dam, which also forms the trailhead of the popular Sawyer Camp Trail.

The Doran Memorial Bridge is the twin pair of steel girder bridges that carry eight lanes of road traffic on Interstate 280 over San Mateo Creek near Hillsborough, California in San Mateo County.

The Nueva School is a private school, with two campuses—the lower and middle school in Hillsborough, and the high school in San Mateo, California—serving gifted students in pre-kindergarten through twelfth grade. Nueva was founded in 1967 by Karen Stone McCown. Originally, the Nueva School only served younger students, but in 2013 it expanded to include a high school, and a new campus for it was built as part of the Bay Meadows development in San Mateo, opening in August 2014.Unique aspects of Nueva's curriculum include its focus on design thinking and social emotional learning. In his book That Used To Be Us, commentator Thomas Friedman lauded Nueva for its creativity-inspiring curriculum and overall philosophy.Nueva is accredited by the Western Association of Schools and Colleges and the California Association of Independent Schools. It has received the Blue Ribbon Award from the U.S. Department of Education in 1988, 1997, and 2010. Nueva was rated the #3 private K-12 school and the #9 private high school in the United States by Niche in 2021.

The Flintstone House is a free-form, single-family residence in Hillsborough, California overlooking and easily seen from the Doran Memorial Bridge carrying Interstate 280 over San Mateo Creek.

The X-100 is an experimental steel house designed by A. Quincy Jones with his partner Frederick Emmons for Eichler Homes and built in 1956 at the San Mateo Highlands development in California. It was listed on the National Register of Historic Places in 2016.

Hillsborough is an incorporated town in San Mateo County, California, in the San Francisco Bay Area. It is located 17 miles (27 km) south of San Francisco on the San Francisco Peninsula, bordered by Burlingame to the north, San Mateo to the east, Highlands-Baywood Park to the south, and Interstate 280 to the west. The population was 11,387 as of 2020.

Odyssey School is a private middle school in San Mateo, California, a town about 15 miles (24 km) south of San Francisco. Odyssey caters to students in grades 6 through 8. Its five academic core subjects consist of writing, mathematics, science, humanities, and Japanese. Offerings in creative arts include drama, choir, music history, pottery, set design, costume design, and photography. The school also teaches swimming, dance, karate, and stage combat under its movement program.Odyssey's theater program includes visits to the Oregon Shakespeare Festival in Ashland, Oregon, where students see and study a cross-section of Shakespeare's plays. The school's Japanese program includes hosting Japanese exchange students each autumn, followed by a three-week trip to Japan at the end of eighth grade, in which students stay at temples and Japanese homes.Odyssey students have won a variety of prizes in outside academic competitions. These include a first place in Notre Dame High School's 2009 Middle Math Contest (out of 190 contestants), and a first place in the 2008 Japanese speech contest of the Japanese Consulate General. Odyssey's programs for helping students cope with stress have attracted regional attention.Many Odyssey graduates attend college-preparatory schools such as San Francisco University High School, Woodside Priory School, Crystal Springs Uplands School, and Menlo School. Others go on to local public high schools. Odyssey graduates later continue their studies at four-year colleges and universities such as UC-Berkeley, Cornell, Occidental, Reed, and Carnegie Mellon.Odyssey was founded in 1998.Odyssey's founding Head of School, Stephen K. Smuin, has been a teacher and school administrator for many years. He had been head of the middle school at the Nueva School, a private elementary and middle school in Hillsborough, California, but was ousted by the school board following allegations of abusive behavior towards a former student. He is the author of three books on writing technique, including "More than Metaphors: Strategies for Teaching Process Writing.". He retired in June 2010. In July 2010, Daniel Popplewell joined Odyssey as its new Head of School. He had been dean of teaching and learning at Bentley School in Lafayette, California. He was succeeded in July 2013 by Stephen P. Lane, who had been head of Santa Barbara Middle School.

Arthur and Mona Hofmann House, also known as the Hofmann House, was built in 1937 and is a historic home located at 1048 Cuesta Road in Hillsborough, California. The building was designed by Modernist architect Richard Neutra in International Style. It has been listed on the National Register of Historic Places since August 5, 1991. The house is a private residence and not open to the public.

The Bridge School is a non-profit organization in Hillsborough, California for children with severe speech and physical impairments. It aims to allow the children to achieve full participation in their communities through Augmentative and Alternative Communication (AAC) and Assistive Technologies (AT). The school was founded by Pegi Young, Jim Forderer and Dr. Marilyn Buzolich in 1986, and has since become a world recognized leader in AAC and AT.