×

Get in Touch

Compass

1440 Chapin Ave #200

Burlingame, CA 94010

Sandy Comaroto

Hillsborough

Prestigious community with spectacular real estate

Welcome to Hillsborough

Hillsborough is an affluent residential community famed for its spectacular properties. The oak-studded San Mateo Mountains rise along Hillsborough’s western border, and the communities of Millbrae, Burlingame, San Mateo, and Haywood-Bays Park bound it to the north, east, and south. Hillsborough’s quiet charm is preserved through zoning laws requiring all lots be larger than half an acre and all homes to be a minimum of 2,500 square feet in size.

 

The real estate includes landmark properties constructed for heirs to some of the United States’ largest fortunes. Standouts include William Polk’s 1912 Uplands estate, the 1939 Skyland farm designed for Big Four railroad magnate heir Charles Crocker, the Frank Lloyd Wright-designed 1939 Sidney Barrett Residence, William Randolph Heart’s Julia Morgan-designed Western White House, and the epic American Renaissance and Beaux-Arts style Carolands mansion. Newer constructions are equally enthralling, with lavish contemporary residences taking inspiration from varied classic and cutting-edge architectural influences.

What to Love

  • Stunning homes

  • Landmark architecture

  • Palm tree-lined streets

  • Burlingame shopping and dining

People & Lifestyle

Hillsborough is one of the mid-peninsula’s most prestigious communities, home to high-ranking executives and prominent figures from business and entertainment. The vibe here is idyllically peaceful and private. Winding streets are lined with palm trees, and the few non-residential properties only add to the community’s allure, with outstanding schools and country clubs.

Dining, Entertainment & Shopping

The many shops and restaurants of Burlingame’s Broadway and Burlingame Avenue are located within minutes of Hillsborough’s northern neighborhoods. There are hundreds of places to shop and dine here, including authentic Italian and Asian cuisine, Brazilian and Korean BBQ, upscale steakhouses, and excellent coffee shops and bakeries such as Copenhagen and Dead Eye Coffee Bar.


The College of San Mateo’s Farmers’ Market is open every Saturday year-round with fresh produce, gourmet foodstuffs, and live music directly south of Hillsborough’s Tobin Estates neighborhood. San Mateo’s lively Downtown district is also a short drive away.

Things to Do

The lavish Carolands estate is one of the most spectacular properties in the entire United States, with an enormous main residence modelled after the court architecture of Louis XIV and gardens in the style of Versailles. Carolands’ charming 1929 Gate House was renovated in 2010 and is now an outpost of the local police department. While Hillsborough is synonymous with elegant architecture and breathtaking, classically inspired design, local landmarks also include the quirky dome-like Flintstones House and a cartoonish statue of “Father of California” Junipero Serra


The historic train station in neighboring Burlingame houses the Burlingame Hillsborough History Museum, showcasing fascinating artifacts and exhibits on the area’s history. The exclusive Burlingame Country Club offers its members access to an 18-hole golf course, tennis courts, and a clubhouse within the heart of Hillsborough, while the scenic Crystal Springs Golf Course is situated immediately to Hillsborough’s west.

Schools

Hillsborough operates its own highly-rated Hillsborough City Elementary School District. Highlights include:

 

  • North Hillsborough School, Public, K-5

  • South Hillsborough School, Public, K-5

  • West Hillsborough School, Public, K-5

  • Crocker Middle School, Public, K-5