Highlands, CA

If you love mid-century modern architecture, the San Mateo Highlands is practically legendary. Built mostly in the late 1950s and early 1960s by developer Joseph Eichler, it is one of the largest collections of Eichler homes anywhere, with more than 700 houses spread across the hillsides. Walking down the streets, you will immediately notice the signature clean rooflines, post-and-beam construction, and modest street facades that open into private courtyards and atriums. Inside, expansive glass walls look out onto backyards and gardens, making the most of California's indoor-outdoor lifestyle. It is a distinctive, cohesive neighborhood where the original architectural character remains remarkably intact.

ATTRMckennagene at English Wikipedia / Public domain

While the Highlands is an unincorporated county pocket with San Mateo mailing addresses, it functions very much like its own small town. Daily community life centers on the Highlands Recreation Center on Lexington Avenue. The rec center is the neighborhood hub, featuring swimming pools, tennis courts, a playground, fitness facilities, and popular year-round programs like summer camps and swim lessons. Commuters also appreciate the location right near Interstate 280 and Highway 92, which makes it easy to drop down into downtown San Mateo for dinner or head off toward San Francisco and Silicon Valley.

ATTRMckennagene ( talk ) / CC BY-SA 3.0

Outdoor access is another major draw. The western edge of the neighborhood borders the Crystal Springs watershed, giving many properties wide-open views across the reservoirs and forested coastal hills. Just down Crystal Springs Road, you can jump directly onto the paved Sawyer Camp Trail, a beloved regional path that traces the water for miles and draws daily walkers, runners, and cyclists. Between the quiet ridgeline setting, direct access to scenic trails, and homes built to take in natural light, the Highlands offers a peaceful, scenic place to settle down on the Peninsula.