Hillsborough, CA: Hillsborough Real Estate - Architectural Legacy Meets Elevated Living

Welcome to Hillsborough, California—a secluded, estate-driven town nestled in the heart of the San Francisco Peninsula. Revered for its historic architecture, lush hillsides, and unparalleled privacy, Hillsborough is a rare blend of Old World elegance and modern refinement. With its large residential parcels, top-performing schools, and architectural pedigree, Hillsborough represents the pinnacle of luxury living in San Mateo County.

Whether you're seeking a grand historic estate, a sleek modern sanctuary, or a discreet off-market opportunity, Hillsborough offers a level of exclusivity that few Bay Area communities can match. And with the Boyenga Team as your trusted real estate partner, you'll gain access to local expertise, architectural insight, and strategic representation in one of Northern California’s most prestigious zip codes.

Geography, Neighborhoods & Character

Unlike most Peninsula cities, Hillsborough is strictly residential—there are no commercial zones, no shopping centers, and no high-density developments. This intentional zoning preserves the area's quiet, retreat-like atmosphere and ensures an exceptionally low population density. With approximately 11,500 residents spread across six square miles of wooded hills, Hillsborough feels more like a private sanctuary than a suburban town.

Distinct Neighborhoods & Estates:

  • Carolands: Home to the iconic Carolands Chateau, this area features sprawling French-style manors on multi-acre lots, many built in the early 20th century.

  • Skyfarm: Known for its commanding views, large parcels, and architectural diversity, Skyfarm blends traditional estates with modern showpieces.

  • Parrott Drive Area: Rich in history, this district includes early-1900s Mediterranean villas and mature landscaping.

  • Uplands: One of the most established neighborhoods in Hillsborough, featuring tree-lined avenues, pre-war architecture, and proximity to top schools.

  • Lower North Hillsborough: Close to Burlingame, this sought-after pocket offers convenience without sacrificing scale or privacy.

  • Homeplace & Tobin Clark Estate Area: Lush landscaping and oversized lots dominate these southernmost neighborhoods, known for gated estates and celebrity residents.

Hillsborough’s topography is characterized by gentle ridgelines, forested canyons, and curving roads. Unlike grid-based towns, each property here is unique—no tract homes, no duplicates, just a mosaic of legacy estates and architectural treasures.

Architecture & Housing Styles

Hillsborough is renowned for its architectural diversity and pedigree. From century-old French châteaux to cutting-edge contemporary builds, the town’s real estate portfolio is both elite and eclectic.

Signature Styles Include:

Beaux-Arts & French Chateau (1900–1930s): Inspired by European grandeur, these homes are often over 8,000 sq ft with formal gardens, imported stonework, and ornate detailing.

Mediterranean Revival: Red-tile roofs, stucco exteriors, and central courtyards are hallmarks of this style, often found in older parts of town like the Parrott Drive corridor.

Mid-Century Modern: Hillsborough is home to several architectural landmarks, including residences by Frank Lloyd Wright (the Sidney Bazett House) and Richard Neutra.

Contemporary & Custom Luxury Homes: Built from the 1990s to present, these homes often feature smart-home integrations, open-plan living, floor-to-ceiling glass, and resort-style outdoor spaces.

Renovated Classics: Many pre-war estates have been tastefully updated with modern kitchens, elevators, and energy-efficient upgrades—maintaining charm without sacrificing comfort.

Due to strict zoning regulations (minimum ½-acre lots) and limited inventory, new construction is rare and highly sought after. Each listing is a one-of-a-kind offering, often trading off-market or through exclusive networks.

Lifestyle & Community

Hillsborough is more than an address—it’s a way of life centered around privacy, education, and refinement. Residents value their space, serenity, and proximity to nature, yet enjoy easy access to elite amenities just minutes away.

Quiet Streets, Gated Homes: Security and solitude define daily life. Most properties are shielded by hedges, gates, or long driveways.

Civic Pride: While there’s no downtown district, Hillsborough maintains a strong civic presence through events like the Concours d’Elegance and Hillsborough Harvest Festival.

Parks & Recreation: Nearby Crystal Springs Reservoir, Sawyer Camp Trail, and Burlingame Country Club offer scenic escapes without ever leaving the area.

Elite Proximity: Hillsborough borders Burlingame and San Mateo, putting residents within minutes of upscale shopping, Michelin-rated restaurants, and SFO International Airport.

Schools & Education

Hillsborough is widely considered one of the best places in California to raise a family, thanks to its top-tier public and private schools.

Public School System:

  • Hillsborough City School District (K–8)

    • North Hillsborough Elementary

    • South Hillsborough Elementary

    • West Hillsborough Elementary

    • Crocker Middle School

All schools boast high test scores, small class sizes, and award-winning STEM, arts, and music programs. The district is supported by a strong parent foundation and consistently ranks among the top 5% of California public schools.

High School:

  • Students typically attend Burlingame High School or Aragon High School, both part of the San Mateo Union High School District. Both offer AP and Honors programs and serve as academic stepping stones to elite universities.

Private Schools Nearby:

  • The Nueva School – A nationally recognized PK–12 progressive school focused on gifted education and design thinking.

  • Crystal Springs Uplands School – Grades 6–12, with a rigorous academic reputation and a historic campus.

  • Junipero Serra High School, St. Matthew’s Episcopal, and Menlo School are also within a 20–30 minute drive.

Hillsborough’s educational ecosystem attracts international buyers, executives, and fiduciary planners seeking long-term academic value.

Real Estate Market & Trends

Hillsborough consistently ranks among the most expensive housing markets in California. Its ultra-low inventory, estate-sized lots, and iconic architecture command a premium unmatched even by nearby luxury markets.

  • Off-Market Sales Are Rising: With privacy paramount, over 30% of high-end Hillsborough listings never hit the MLS.

  • Architecturally Significant Homes in Demand: Mid-century modern, Usonian, and period-revival properties often receive premium offers.

  • Inventory Scarcity Driving Value: Lot splits are restricted; estate preservation is prioritized over density.

In short, Hillsborough is a hold-and-appreciate market. Buyers value its long-term exclusivity and low turnover. Sellers benefit from global demand and a growing appetite for historic or custom-designed homes.

Why Choose Boyenga Real Estate

  • Architectural Expertise: From Neutra to Normandy, we understand the nuances of architectural value and preservation.

  • Access to Off-Market Listings: Through the Compass Private Client Network, we provide access to estate opportunities not found online.

  • Concierge Marketing: Cinematic video, drone flyovers, AI-enhanced staging tools, and bespoke listing experiences.

  • Discreet Representation: Trusted by fiduciaries, attorneys, and family offices for confidential sales and valuations.

  • Luxury Vendor Network: White-glove connections to stagers, contractors, landscape designers, and private lenders.

Whether you're restoring a 1920s villa or buying a newly constructed hilltop compound, the Boyenga Team will provide the vision, resources, and results you deserve.

Contact the Boyenga Real Estate Team today to embark on your Hillsborough real estate journey. Experience the difference that true expertise and dedicated service can make.