Nestled between the dramatic slopes of the Santa Cruz Mountains and the spirited vitality of San Mateo on the bay coast, the town of Hillsborough is renowned for its affluence and sophistication. Entirely residential, Hillsborough is an idyllic haven of winding driveways, stately homes, a private community, and acres of lush open spaces.

The historic Hillsborough was built on the dream of establishing an elegant residential enclave. At the time of its incorporation in 1910, Hillsborough was renowned for its mega-estates and millionaire lifestyle, which continued to evolve as the population grew. Today, Hillsborough maintains its charm through strict zoning regulations and property lot sizes, ensuring that the quiet peace of the city stays intact.

Homes in Hillsborough are often tucked on the hillsides for breathtaking views of the Bay Area, and lavish, multimillion-dollar mansions and estates are the norms here. While all homes in Hillsborough are effortlessly regal, they vary significantly in architectural styles and histories. In Hillsborough, it’s possible to encounter everything from highly modern, sleek single-family abodes designed by top architects to historic, French-Normandy-style estates perfect for fairytale living.

Residents in Hillsborough have the luxury of homes that often feature access to hiking trails and open park spaces, and everything needed to revel in the beauty of the San Francisco Peninsula is right at your fingertips. It’s a calm, family-focused community with strong ideals and a commitment to maintaining its values.

While the area of Hillsborough is entirely residential, the neighborhood is conveniently perched just minutes away from the multitude of retail and commercial districts of both San Mateo and Burlingame. Only a ten-minute drive out, the Burlingame Avenue shopping area houses plenty of locations to satisfy your retail needs, including well-known brands such as lululemon, Pottery Barn, Apple, and Amazon.

Other ventures for entertainment include visiting the Hillsdale Shopping Center, which features dozens of top-tier stores and includes restaurants ranging from American grill classics to sushi delights, niche local favorites, and chains like Jamba Juice and Starbucks.

More than just good eats and incredible retail, Hillsdale Shopping Center is among the top destinations in San Mateo, thanks to establishments like Red Door Escape Room, Sandbox VR, and Pinstripes. At the on-site Cinépolis Luxury Cinemas, your movie viewing experience comes with a catered gourmet meal.

Even with the plenitude of activity in nearby cities, the village of Hillsborough often prefers to come together and embrace its strong, community-centered gatherings and events that help foster its warm, friendly atmosphere. Among those events is the area’s farmers market, known as The Old Church Farmers Market thanks to its quaint venue. Hot coffee, fresh produce, and local vendors are the stars of the show here, with the shimmering California sunshine backlighting it all.

Put together and hosted by the Hillsborough School Foundation, the annual Fun Run is an event for the whole family, with kids and grown-ups alike choosing to walk or run their 2K, 5K, and 10K races that benefit the schools. The Concours Car Show, held on the Crystal Springs Golf Course, works to preserve a generational love of exotic, vintage, and rare automobiles, and the proceeds of the event are donated to charities in the community.

As a Bay Area neighborhood, Hillsborough has access to a number of incredible schools. Top educational opportunities include: