The largest city in its namesake San Mateo County, San Mateo, is a vibrant community just south of San Francisco and in the heart of the peninsula. With a large Central Park, the famous CuriOdyssey at Coyote Point Museum, a charming downtown area, lined with historic buildings, and destination restaurants and upscale shopping at the Hillsdale Shopping Mall, San Mateo is an incredible place to live and call home. For those interested in the arts, the San Mateo Performing arts center is a magnificent venue to take in a concert or a show. You can also check out the San Mateo Arboretum and the Japanese Tea Garden for exquisite horticulture displays while visiting the town.

San Mateo was once home to the Bay Meadows Race Track, which was (until its closure) the longest-running thoroughbred racetrack in California. Heading to see the ponies was a fond memory for many residents, but the land proved too valuable to operate as a horse racing track. Bay Meadows is now a hip and urban master-planned development that will include apartments, townhomes, condominiums, smaller lot single-family homes, and some commercial space. The proximity to the Caltrain station nearby makes this an ideal housing location for those looking to commute up and down the peninsula.

Elementary school-aged children attend schools within the San Mateo-Foster City School District. The San Mateo schools in the district do not carry the same high marks as the Foster City schools, but they are considered good mid-range schools. High school-aged children in the area attend one of the regional schools in the San Mateo Union High School District. As an alternative, Junipero Serra High School is a local private school located in the heart of the city and includes notable alumni such as Tom Brady and Barry Bonds.