Hillsborough

Located just north of Silicon Valley, Hillsborough is one of the wealthiest communities in America. The town is unique because of its no commercial zoning law and many large homes – the minimum square footage allowed for a home is 2,500 with a minimum lot size of half an acre. Boasting an illustrious, colorful, and affluent history, no other suburban town matches the heritage of distinguished living in Hillsborough. With its phenomenal schools, town government facilities, a private golf course, wooded areas plus views of the San Francisco Bay, the town thrives on its core foundations as a beautiful place for sophisticated living as well as a great place for families.

From its glorious, historic mansions to its wonderfully rustic feel, you’ll understand why Hillsborough is so frequently ranked as one of the most coveted places to live in the country. From the moment you first step foot in this affluent, beautiful enclave, you will see wonders all around. Situated in San Mateo County on the gorgeously scenic San Francisco Peninsula, this verdant town is known for its peaceful ambiance, lush greenery, and privacy. This idyllic neighborhood is also home to award-winning schools and exceptional public services.

Its prime location promises residents and guests a welcome respite from the hustle and bustle of the city but just enough proximity to San Francisco to savor the art and culture the mega-destination offers. Staggering views of the Bay and an abundance of impeccable open space make the town fertile ground for a range of delightful outdoor activities, including golfing, hiking, and cycling. To top it all off, Hillsborough prohibits commercial spaces, giving the exclusively-residential town a thoroughly serene ambiance.

What to Love

• Booming with gorgeous natural splendors
• A sublime, Mediterranean climate
• Near Burlingame, San Francisco, and Silicon Valley
• Deemed one of the most prestigious places to live in the U.S.

History and Heritage of Hillsborough, CA

Hillsborough, California, is steeped in a rich history that traces back to the mid-19th century, beginning its narrative as a part of the vast Rancho San Mateo. The land that would become Hillsborough was purchased by William Davis Merry Howard, a New Englander turned San Francisco business titan, who bought the 6,500-acre rancho from Cayetano Arenas in 1848. Howard's acquisition marked the beginnings of a community that would evolve into one of the most affluent and exclusive locales in the United States. By the time California became a state in 1850, Howard had solidified his holdings, establishing a grand estate called "El Cerrito." Despite Howard's early death in 1856, his legacy paved the way for Hillsborough's development as a residential haven for San Francisco's elite.

The incorporation of Hillsborough in 1910 was driven by local estate owners' desire to preserve the area's rural character, free from the urban encroachments of neighboring areas like Burlingame. This led to the establishment of a community with strict zoning laws that emphasized large, secluded properties—a character that Hillsborough retains to this day. The early 20th century saw the construction of magnificent mansions and the subdivision of large estates, which attracted further affluent residents seeking a bucolic lifestyle near the city. As the town evolved, it maintained a commitment to preserving its unique character, devoid of commercial development, thus ensuring its status as a quiet and exclusive enclave.

Local Lifestyle

Hillsborough is composed solely of homes — and the beauty of nature. This naturally lends itself to a tight-knit community feel, which is one of the leading reasons people choose to settle down in this area.

The majestic estates throughout Hillsborough are also a magnet for luminaires ranging from Elon Musk to Alicia Silverstone. You’ll often find your neighbors gathering together for barbecues or happen upon them on one of the region’s lush, pristine hiking trails.

Dining, Shopping & Entertainment

While Hillsborough itself maintains a strictly residential character—no commercial zones or retail storefronts—the town is ideally situated just minutes from San Mateo and Burlingame, where a refined culinary and entertainment scene awaits. Residents enjoy privacy and tranquility at home, paired with effortless access to top-tier dining and leisure options nearby.

Fine Dining & Local Favorites:

• All Spice (San Mateo) – A Michelin-recognized favorite, offering modern Californian cuisine with global influences in a charming Craftsman house setting.
• Café Figaro (Burlingame) – A go-to for European-style brunch and elegant bistro dinners, with a sophisticated wine list and al fresco seating.
• Viognier (San Mateo) – Located above Draeger’s Market, Viognier is an elevated dining experience combining French technique with local ingredients—ideal for special occasions.
• Backhaus (San Mateo) – This artisan bakery draws loyal fans for its sourdough, morning buns, and coffee—a favorite stop after school drop-offs or weekend errands.

Luxury & Social Clubs:

• The Peninsula Golf & Country Club – Founded in 1911, this exclusive members-only club features a renowned 18-hole golf course, fine dining, tennis courts, and social events.
• Crystal Springs Golf Course – Just west of Hillsborough, it offers panoramic views over Crystal Springs Reservoir, plus a relaxed, semi-private golfing experience.

Entertainment & Culture:

• The San Mateo Performing Arts Center – Just minutes away, this 1,500-seat theater hosts Broadway-style productions, symphonies, and community performances.
• Downtown Burlingame Avenue – A lifestyle destination in its own right, with boutique shopping, craft cocktail bars, and upscale dining. Local hot spots like Limon Rotisserie and Mingalaba round out the diverse offerings.

Parks & Recreation

Hillsborough is a haven for nature lovers and those seeking an active, outdoor lifestyle. With its rolling hills, mature forests, and expansive private lots, the town offers both serene privacy and access to a wealth of recreational opportunities in the surrounding area.

Parks & Open Spaces: 

While Hillsborough does not operate public parks within its boundaries, nearby Coyote Point Recreation Area (San Mateo) and Burlingame’s Washington Park offer family-friendly outdoor spaces with picnic areas, playgrounds, and scenic bay views.

Hiking & Nature Trails:

• Crystal Springs Regional Trail – A local favorite that runs along the Crystal Springs Reservoir, offering 15+ miles of paved and dirt paths ideal for walking, biking, or jogging. The Sawyer Camp Trail section is especially popular for weekend strolls.
• Pulgas Ridge Preserve (a short drive away) – Pet-friendly with well-maintained trails and scenic ridge views, it’s great for dog owners and families alike.
• Edgewood Park & Natural Preserve – Known for its spring wildflowers and moderate trails, it offers a quieter hiking experience just minutes from town.

Equestrian & Country Living: The area’s expansive estates and zoning laws support equestrian-friendly properties. Residents who keep horses often use private facilities or nearby riding centers like Folger Stable in Woodside, which offers boarding, lessons, and guided trail rides.

Coastal & Bay Activities: Just a 20-minute drive west, Half Moon Bay offers surfing, horseback riding on the beach, and miles of coastal hiking along the Coastal Trail. Closer to home, Coyote Point Marina supports sailing, kayaking, and waterfront picnicking with bay breezes.

Arts and Culture

Hillsborough, California, embodies a rich mix of arts and culture, primarily supported and celebrated through community initiatives and local organizations. The Hillsborough Arts Council plays a pivotal role in this, dedicating over 50 years to fostering the arts within the community. This council enriches local life by supporting artists and arts organizations, investing in arts programs, and enhancing cultural access throughout the area. The absence of commercial entities within Hillsborough's borders accentuates its unique cultural scene, focused on private events, historic architecture, and local art exhibitions, rather than commercial art galleries or theaters. The town’s commitment to maintaining its residential charm contributes to a vibrant community life where arts and cultural activities are deeply integrated into the social fabric, supported by events and educational programs that engage residents of all ages

Commute & Traffic in Hillsborough, CA

Commute and traffic in Hillsborough, CA, are influenced by the town's geographic location and community structure. Hillsborough is part of the San Mateo County, which is serviced by Commute.org, an organization dedicated to reducing vehicle miles traveled and encouraging the use of sustainable transportation alternatives. This includes promoting carpooling, cycling, and the use of public transit like Caltrain and BART to help alleviate congestion and enhance the quality of life for residents.

For those commuting to schools like The Nueva School, which has campuses in Hillsborough and nearby San Mateo, a variety of transportation options are available. The school coordinates regional bus services, promotes carpooling, and provides Caltrain passes to facilitate access to its campuses. This reflects the broader community’s efforts to ensure efficient and sustainable commuting practices across the region​.

Schools & Education

Children who reside in Hillsborough have the option to attend one of the town’s top-performing public schools, such as:

Families are drawn to Hillsborough not just for its scenic beauty and privacy—but also for its nationally recognized schools. The town offers a blend of prestigious public education and elite private institutions, creating one of the most academically competitive environments in the Bay Area.

Top-Ranked Public Schools (Hillsborough City School District):

Hillsborough is served by the Hillsborough City School District (HCSD), which operates three elementary schools and one middle school, all of which are consistently ranked among the best in California.

• North Hillsborough Elementary – Known for its nurturing environment and enrichment programs in art, science, and technology.
• South Hillsborough Elementary – A California Distinguished School with strong parent involvement and academic excellence.
• West Hillsborough Elementary – Offers a whole-child education model, emphasizing social-emotional learning alongside academics.
• Crocker Middle School – Ranked among the top middle schools in San Mateo County, Crocker boasts high test scores, robust music and arts programs, and dedicated STEM pathways.

According to GreatSchools.org, HCSD schools routinely earn scores of 9 or 10 out of 10, and the district benefits from strong community funding through Hillsborough Schools Foundation (HSF), which raises millions annually to support programs not covered by state funding.

Private School Options: 

For those seeking private education, Hillsborough and nearby communities offer a wealth of top-tier institutions:

• Crystal Springs Uplands School – A nationally ranked 6–12 college preparatory school known for academic rigor and a selective admissions process.
• The Nueva School – An innovative K–12 school focused on gifted education, design thinking, and project-based learning.
• Junipero Serra High School – An all-boys Catholic school in nearby San Mateo offering strong academics and championship athletics.
• Sacred Heart Prep and Menlo School – A short drive away in Atherton and Menlo Park, both schools offer rigorous college-prep curricula and elite college placement records.

From STEM-forward public education to Silicon Valley’s most prestigious private institutions, Hillsborough offers families a future-forward academic ecosystem backed by community commitment and excellence.

Community Guides

• History of Hillsborough
• Hillsborough real estate for sale
• Architectural Review Board
• Hillsborough Residential Design Guidelines
• Town Info Mailer
• Hillsborough Garden Club​​​​​​​​​​​​​​

In 2024, the Hillsborough average price for a home was $5,837,955, a 5% decrease from the previous year.​​​​​​​

Local Culture

Hillsborough may be a quiet residential enclave, but beneath its serene streets lies a deeply engaged, philanthropic, and creative community. The town’s culture revolves around civic pride, artistic expression, and a strong tradition of giving back.

Art, Music & Local Talent

Though Hillsborough has no commercial downtown, it is home to a vibrant community of artists, musicians, and design professionals—many of whom exhibit regionally or teach at local institutions. Community events such as the Hillsborough Concours d’Elegance not only showcase rare classic cars, but also support children's charities and reflect the area’s blend of luxury and local spirit.

Nonprofits & Civic Engagement

Hillsborough residents are known for deep involvement in philanthropy and education. The Hillsborough Schools Foundation (HSF) and Hillsborough Beautification Foundation are two of the most active nonprofits in the area. These organizations fund public art, environmental projects, and extracurricular programs that enrich daily life and strengthen neighborhood ties.

Signature Events & Gatherings:

• Hillsborough Memorial Day Parade – A beloved community tradition featuring local schools, scout troops, marching bands, and fire trucks.
• Hillsborough Harvest Garden Party – Hosted annually at a local estate, this fundraiser blends farm-to-table cuisine, fine wine, and community spirit—all in support of local schools.
• Concours d’Elegance – A nationally recognized vintage car show, held on the fairways of Crystal Springs Golf Course, attracting collectors and donors from across the Bay Area.

Lifestyle Personality: Discreet, community-focused, and intellectually curious—Hillsborough residents often include tech founders, investors, medical professionals, and creatives. The local lifestyle is defined by luxury with restraint: think school fundraisers that feel like garden galas, architecture that leans toward heritage estates, and a culture that values both excellence and privacy.

Architectural Styles in Hillsborough

The architectural landscape of Hillsborough reads like a curated gallery of elite design. From historic revival mansions to cutting-edge modern residences, the town’s homes are as distinctive as they are private. Because of large lot sizes and strict zoning, homes here are typically custom-built or heavily tailored—resulting in a striking range of architectural expressions.

Notable Styles & Design Terms:

• Mediterranean Revival – Think terracotta roofs, arched doorways, and wrought iron details. Popularized in the 1920s, these homes remain iconic in areas like Hillsborough Park.
• French Chateau & Normandy – Stone façades, turreted entries, and manicured formal gardens define this storybook style. Often found on gated estates.
• Modern & Contemporary – Sleek glass façades, open floor plans, and seamless indoor-outdoor living. Many feature panoramic views and LEED-certified construction.
• Mid-Century Modern – A more subtle presence, but notable in homes built during the 1950s–60s, especially with post-and-beam construction and clerestory windows.
• Colonial & Tudor Revival – Brick and timber exteriors, leaded glass windows, and grand staircases reflect Hillsborough’s early 20th-century architectural roots.

Notable Architects & Influences:

• Willis Polk – A famed Bay Area architect, Polk designed several early Hillsborough estates blending classical and Arts & Crafts influences.
• Julia Morgan – While best known for Hearst Castle, Morgan’s influence is felt in some of the town’s historic homes.
• Swatt | Miers Architects – Known for contemporary luxury homes across the Peninsula, with minimalist lines and sustainable design.
• Farro Essalat – A local designer renowned for Mediterranean-inspired mansions with indoor courtyards and artisan detailing.

Micro-Neighborhood Aesthetics:

• Skyfarm & Homeplace – Often showcase contemporary and new-construction homes with valley views.
• Lower North Hillsborough – Known for grand pre-war estates and vintage architecture on tree-lined streets.
• Carolands – Site of the famous Carolands Chateau, this enclave is home to some of the most iconic historic properties in the Bay Area.

Real Estate in Hillsborough

Hillsborough real estate offers an extraordinary blend of exclusivity, privacy, and architectural pedigree—positioning it among the most desirable residential markets in Northern California. With no commercial zoning and strict development codes, every home in Hillsborough is situated on a minimum half-acre lot, offering spaciousness that’s rare in the Bay Area.

Property Styles & Offerings: Hillsborough is known for sprawling estates, custom-built mansions, and legacy properties. You’ll find everything from classic European-inspired manors to sleek contemporary builds tucked into the hillside. Whether you're looking for a restored 1920s villa or a modern home with smart tech and clean lines, the architectural diversity here is exceptional.

• Median List Price (Q1 2025): $6.8M
• Typical Lot Size: 0.5 to 2+ acres
• Average Days on Market: ~37
• Luxury Threshold: Homes above $10M are not uncommon, especially in areas like Hillsborough Oaks and Skyfarm

Prestige Meets Privacy: Because the town maintains no commercial real estate or condominiums, Hillsborough appeals to ultra-high-net-worth buyers seeking serenity within reach of Silicon Valley, SFO Airport, and San Francisco.

Explore available listings on our Hillsborough MLS page to find the perfect estate for your lifestyle. You can also browse by type, including condos, luxury homes, and lands for sale in Hillsborough, San Mateo, CA

BREWER SUBDIVISION / UPLAND

The Brewer Subdivision affords its residents the perfect blend of lush, leafy green serenity and urban convenience. Homes here are in the mid to high range for the Hillsborough real estate market, and the inventory includes many large and newer builds. As of 2024, prices for single-family homes here range from $8,150,000 to $23,000,000.

This neighborhood offers proximity to El Camino Real, and it is the closest Hillsborough neighborhood to downtown San Mateo, where residents enjoy myriad restaurants and retail.
​​​​​​​
Schools for this neighborhood include San Mateo High School, Crystal Springs Uplands School, Crocker Middle School, and South Hillsborough Elementary School

CAROLANDS

Real estate in the Carolands community rarely comes on the market, a testament to residents’ attachment to this area. When homes do come up for sale, inventory includes classic and contemporary homes and remodels, some with extra-large lots and views out to the Bay. Price ranges, too, can vary; as of 2024, prices for single-family homes here range from $3,439,000 to $7,380,000.

This neighborhood offers commuter convenience with proximity to Highway 280, while the restaurants and retail on Burlingame Avenue are only a 2-mile drive.

​​​​​​​Schools for this neighborhood include top-rated West Hillsborough Elementary School, North Hillsborough Elementary School, Crocker Middle School, and Burlingame High School.

COUNTRY CLUB MANOR

Real estate in Country Club Manor doesn’t often come up for sale, but when it does, inventory includes newer and larger homes set against the neighborhood’s lush, leafy green surroundings. As of 2024, prices for single-family homes here range from $4,250,000 to $6,250,000. This neighborhood offers proximity to Burlingame Country Club for golf on its 18-hole course.

​​​​​​​Schools for this neighborhood include Burlingame High School, Crocker Middle School, and top-rated North Hillsborough Elementary School.

HILLSBOROUGH HEIGHTS

Though its name might suggest otherwise, residents of Hillsborough Heights enjoy homes set on lovely level streets. The housing inventory here includes older, distinguished homes with styles including Mediterranean and Tudor. As of 2024, prices for single-family homes here range from $3,850,000 to $18,800,000.

This neighborhood offers commuter convenience and walkable proximity to retail and restaurants in downtown San Mateo.

​​​​​​​Schools for this neighborhood include San Mateo High School, Crocker Middle School, and South Hillsborough Elementary School.

HILLSBOROUGH HILLS

Offering classic and contemporary homes in a variety of architectural styles, set among abundant trees, and with views out to the Bay, it’s little wonder that properties seldom come up for sale in Hillsborough Hills. As of 2024, prices for single-family homes here range from $3,600,000 to $6,544,800.
​​​​​​​
Schools for this neighborhood include West Hillsborough Elementary, North Hillsborough Elementary, Crocker Middle School, and Burlingame High School.

HILLSBOROUGH KNOLLS

Hillsborough Knolls is a well-established community in Hillsborough, California. Homes here include a range of architectural styles and time periods. As of 2024, prices for single-family homes here range from $3,850,00 to $8,000,000.

HILLSBOROUGH OAKS

For homebuyers in search of seclusion, the Hillsborough Oaksbridge neighborhood offers privacy and larger lots in a wooded setting. Real estate in this neighborhood includes pre-war homes, estates, and newer builds, with the notable absence of ranch-style homes, which makes it unique in Hillsborough. As of 2024, prices for single-family homes here range from $4,300,000 to $9,000,000.

This neighborhood offers walkable proximity to Broadway Avenue in Burlingame for restaurants and retail, and it is conveniently close to Highway 101 and El Camino Real.
​​​​​​​
Schools for the Hillsborough Knolls neighborhood include North Hillsborough Elementary School, Crocker Middle School, and Burlingame High School.