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HILLSBOROUGH, CA:  One of America's most illustrious luxury suburbs.

Hillsborough...its very name exudes timeless prestige. With origins tracing to the Gold Rush, Comstock Lode, and "Big Four" railroad barons, this legendary hamlet continues to represent the ultimate in Peninsula residential luxury within 30 minutes of both San Francisco and Silicon Valley. Dating to the 1890s, the Town of Hillsborough was originally inspired by Francis G. Newlands after his East Coast country club community of Chevy Chase, Maryland. Today, Hillsborough still maintains its meandering country roads revolving around the Burlingame Country Club and pristine nature. Lush topography cradles the many unique architectural properties. From dramatic canyons and forested hillsides, to hidden lanes and sweeping Bay vistas, Hillsborough's "treescape" natural environment defines its instantly recognizable thumbprint.

Cruising along the bucolic lanes you can still observe vestiges of historic estates from 19th century society families such as the Crockers and Spreckels. But today's Hillsborough brings a new dynamic perfectly aligned with the Bay Area's booming industries of private equity, technology, venture capital, and biotech.  Many captains of these fields choose to call Hillsborough home for its singular lifestyle attributes. Standout assets include world-class public and private schools, proximity to downtown Burlingame and San Mateo, quick connections to International airports, San Francisco, and Silicon Valley. But it's the charismatic quality of the housing inventory that will capture your heart: grand estates of the 1920s and 1930s are mixed in with newer developments and exciting state-of-the-art constructions. An understated country resort ambiance prevails with privacy hedges, gates, and epic trees that shroud worldly architecture, pools, and vast gardens.

Hillsborough is partitioned into 10 distinct neighborhoods. I have articulated these areas by authoring the site The Town's regions are generally discussed in terms of "Lower Hillsborough" or "Mid" or "Upper Hillsborough" based on proximity to El Camino in the flats (Lower) or proximity to Highway 280 further up the hill (Upper). As viewed on my map, Lower Hillsborough neighborhoods include Lower North and Lower South, while "Mid Hillsborough" areas include Mid North (upper Barroilhet, Homeplace, San Raymundo, El Arroyo, etc) and Mid South (around Vista Park such as Culebra, Vista, Ridgeway). Neighborhoods closer to 280 in Upper Hillsborough include Carolands, Skyfarm, and Highlands/Lakeview. As each nieghborhood occupies a different era of development, the housing stock will vary. Lower Hillsborough has the most heritage (1910s-1940s) properties often on larger flat lots, while a community such as Skyfarm derives from the 1970s-1980s with executive homes of that period. Throughout Hillsborough, the real estate desirability has spurred new construction and re-development as well. Many modern designs and newer luxury floorplans continue to proliferate as older properties are re-purposed.

Some residents prefer Lower Hillsborough's proxmity to Burlingame Avenue or downtown San Mateo amidst flat streets, while others seek a quick connection to Highway 280 or scenic Bay views found in the upper neighborhoods. Lower Hillsborough is generally regarded as the most expensive, although eight-figure estates are also found in neighborhoods of Mid North, Mid South, Carolands, and Skyfarm. Bordering San Mateo at the southwest corner of Hillsborough, you will find the enclaves of Tobin Clark and Parrott Drive area. These outlying districts are positioned beyond the "heart of Hillsborough," but do offer a strong number of larger homes from the 1980s-2000s, and indisputably some of the best views in Town. Whichever neighborhood you choose, owning a home in Hillsborough promises the San Francisco Bay Area's premier luxury lifestyle at a location that is truly a word, timeless.

For more detailed information please visit and view all currently available Hillsborough homes here. Text Geoffrey: 650-455-3735

-Content by Geoffrey Nelson. 2017

"Geoffrey Nelson Markets and Sells Hillsborough's Most Interesting Homes." I have sold all of the unique Hillsborough homes below:


Location Cubed

MBA Real Estate Appraisal

Local veteran appraiser with a passion for detail and extensive nuanced knowledge

  • (650) 348-5798
  • Burlingame, CA 94010

TRG Architects

  • 650.579.5762
  • Burlingame,

Charlie Barnett Associates

Recently exectued a brilliant renovation for a client on Eucalyptus Avenue, Lower Hillsborough, seamlessly blending elements of traditional and modern. 

Winges Architects

Wells Fargo Home Mortgage

First Republic Bank

Regional Managing Director who has helped flawlessly with many of my clients from the Private Equity field, among others. 

First Republic Bank

Senior Managing Director and a pleasure to deal with at any price point. 

With Fencing

Scott With

  • 650-222-4774

Dean Icardi

First, Last & Always

Premium high-end specialist who executed beautiful walnut flooring in a Hillsborough modern I represented, among other architectural showcase homes

  • 415-541-7978
  • San Francisco, CA 94107

State Farm Insurance

Impeccable personal service and immersed in the local community.

Ken Fulk Design

  • 415-285-1164
  • San Francisco, CA

Blue Sky Designs

Fitzgerald Landscapes

  • 650.548.0145

Michael Callan, Landscape Architect

Fabulous reputation and track record working with high-end projects across the Peninsula and many in Hillsborough, Burlingame, and San Mateo

Celtic Moving & Storage Co.

  • (415) 307-8699
  • San Francisco, CA 94124

Wilkinson Construction

One of Hillsborough's top-tier custom builders, having executed extraordinary new constructions recently on streets such as Roblar, El Cerrito, and Parkside. 

  • 650.333.7607
  • San Mateo, CA 94402

All Wood Construction

Strong portfolio in Hillsborough, San Mateo, Burlingame, for expansions and renovations. Excellent personalized family service. 

  • 650-366-9521

Peninsula Custom Homes

Grand scale custom projects throughout Hillsborough and surrounding areas. 

A&R Termite

30-year veteran and highly regarded in the Realtor community. 

  • 650-347-9512
  • San Mateo,

North American Title Company, Inc.

Fidelity National Title