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Olivia Decker
  • Lic.# 00712080
Golden Gate Sotheby's International Realty
Golden Gate Sotheby's International Realty home

Though it’s one of the wealthiest cities in Santa Clara County – and in the U.S. – you don’t hear as much about Monte Sereno as you do about other affluent Bay Area towns. Some assume it’s either part of Los Gatos or part of Saratoga; it’s not. Monte Sereno is bordered by those cities, but it’s a distinctly separate place.

To begin with, Monte Sereno has no commercial buildings within its borders. That means no downtown, no shopping centers, no restaurants. This may sound like a challenge, but you’ll find no complaining among residents. Their retail and dining needs are more than met by options in neighboring Los Gatos and Saratoga, and the upside – a quiet, all-residential community almost exclusively made up of single-family homes on large lots – is exactly what they signed up for when they chose to make their homes in Monte Sereno.

Part of what draws people to Monte Sereno is its bucolic setting. Like Los Gatos and Saratoga, it’s nestled into the western foothills of the Santa Cruz Mountains, removed from the hustle of Silicon Valley but still only 15 minutes from Apple, 20 minutes from Yahoo and 25 minutes from Facebook headquarters in Menlo Park. That distance is exactly right for executives looking to escape the pressure of the work week. A few miles away lies utopia: beautiful trees, luxurious homes, friendly neighbors, and quiet, winding streets.

As you might imagine, all of this paradise does not come cheaply; Monte Sereno is where you will find some of the Bay Area’s priciest residential real estate with property values in line with Atherton, Woodside, Hillsborough and its closest neighbors, Los Gatos and Saratoga.

Monte Sereno is defined almost as much by what you won’t see as by what you will. What you won’t see are parking lots and shopping malls or identical houses crowded next to each other on treeless subdivision streets. In fact, if you drive up and down Monte Sereno’s narrow streets – many of which end in cul-de-sacs – you won’t see very many homes at all. Most of them are hidden behind the trees.

One home you definitely won’t see is the modest ranch home once owned by Beat Generation icon Neal Cassady. Though known for his wanderings, Cassady lived a fairly conventional life on Bancroft Avenue in Monte Sereno during the 1950s, raising his children there in a home that was razed in 1997. In its place now is a much larger, two-story home more consistent with modern Monte Sereno but somewhat lacking in legend.

Years ago, Monte Sereno, like Los Gatos, was popular with artistic types. Cassady and John Steinbeck were the most famous of countless writers, painters, dancers and general bohemians who came to the wooded Santa Cruz mountain foothills for inspiration – and cheap rent – before and after World War II. In 1936, Steinbeck built himself a small cabin in what was then Los Gatos but is now Monte Sereno. There he wrote “The Grapes of Wrath” and “Of Mice and Men” before moving out in 1938.

Nineteen years later, in 1957, Monte Sereno incorporated as an attempt to stave off what locals felt were efforts to change the town’s rural atmosphere. Incorporation helped, but today’s Monte Sereno, while still ruled by narrow roads and big trees, is no longer a refuge for the unorthodox and artistic. Instead, it’s a haven of serenity for those who’ve made it to the top of the mountain and are hoping it includes a little peace and quiet.
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