Los Gatos

Los Gatos sits right where the valley floor runs into the Santa Cruz Mountains, which gives the town about 11 square miles of terrain that changes character every few blocks. Roughly 32,600 people live here, a number that has edged down since 2020, and the median age of about 45 is noticeably older than most of Silicon Valley. It incorporated in 1887, making it one of the oldest towns in Santa Clara County, and that head start shows in a downtown that grew up around real buildings instead of shopping center parking lots. It is also the most expensive of the towns I work in regularly, and I would rather say that plainly than dance around it.

The town began as a mill site. James Alexander Forbes built a flour mill on Los Gatos Creek in the 1850s, and the settlement that grew around it was known by the mill’s name before it took the one from the Spanish land grant, Rancho Rinconada de los Gatos, a reference to the mountain lions and bobcats in the surrounding hills. Logging came first, then orchards of apricots, prunes and grapes, and there was even a modest oil boom between 1891 and 1929 that most people have forgotten. By the 1920s Los Gatos had become something of an arts colony, drawing writers, musicians and film people, with John Steinbeck, violinist Yehudi Menuhin and the actresses Joan Fontaine and Olivia de Havilland all spending time here.

Downtown runs along Santa Cruz Avenue and Main Street, and it is the reason a lot of people fall for this town in the first place. Restored storefronts, the 1880 Forbes Mill Annex, the Old Town center and a genuinely good restaurant scene make it a place you walk rather than drive through. Every September the Kiwanis Club puts on the Los Gatos Art and Wine Festival, a tradition since 1971 that fills the civic center lawn on East Main Street for a weekend. The Los Gatos Chamber of Commerce keeps a current calendar of the smaller events that fill in the rest of the year.

For anyone thinking about how they will spend their days after they stop commuting, the outdoor access here is the real draw. Vasona Lake County Park covers 152 acres with flat paths, boat rentals and shade, and it connects to the town-owned Oak Meadow Park, where the Billy Jones Wildcat Railroad and the old carousel have been entertaining grandchildren for generations. The Los Gatos Creek Trail runs nearly ten miles from here through Campbell and into San Jose, all of it paved and level enough for a daily walk regardless of what your knees are doing.

Town services for older residents are better than the size of the place would suggest. The Adult Recreation Center on East Main Street is home to the town’s senior services program, and LGS Recreation runs a full slate of classes, trips and fitness offerings for the 55 and over crowd jointly with Saratoga. El Camino Health’s Los Gatos Hospital on Pollard Road is right in town, which is a meaningful advantage over neighbors that have to drive to San Jose. The Los Gatos Public Library on Villa Avenue is town-run rather than part of the county system, and it is a genuinely nice building to spend an afternoon in.

Public schools here are split between two districts, with Los Gatos Union School District covering kindergarten through eighth grade and the Los Gatos-Saratoga Union High School District running the high schools for both towns. School reputation drives a large share of buyer demand in Los Gatos, and it shows up directly in what a house sells for, even when the sellers have been empty nesters for thirty years.

Getting around means Highway 17 and Highway 9, and anyone who has lived here a while has an opinion about both. Highway 17 puts you in downtown San Jose in twenty to twenty-five minutes when traffic cooperates and considerably longer when it does not, and it is the road over the hill to Santa Cruz. There is no light rail service into town, so VTA buses connecting to the Winchester station in Campbell are the transit option, and Caltrain requires a trip to Diridon. Netflix keeps its headquarters here and is the town’s largest employer, which is part of why the local economy has stayed steady through some rough stretches for tech.

The housing stock refuses to be summarized in one sentence, and that is part of the appeal. You will find Victorian and Craftsman homes on the small lots of Almond Grove near downtown, mid-century ranch homes on the flatter streets, and large contemporary and Mediterranean houses on multi-acre parcels as you climb toward the mountains. For downsizers the picture is tighter than I would like, because attached housing is limited, but the condominiums at Rinconada Hills and the newer units near North Santa Cruz Avenue do come up, and neighboring Monte Sereno offers a different mix again. If you are in a hillside house with a long driveway and a flight of stairs to the front door, we should talk about timing before the house makes the decision for you.

The market here has stayed strong. Through the summer of 2026 the median sale price has been running around $2.7 million, up roughly six and a half percent from a year earlier, with homes going into contract at a median of about 23 days. Los Gatos is one of the few places in the county where prices are still climbing rather than flattening, largely because inventory stays so thin. My Los Gatos home prices page tracks how those numbers have moved, and I keep it current as sales close.

If you have owned in Los Gatos for decades, your equity position is probably larger than you have let yourself think about, and the tax and estate questions that come with it are genuinely complicated. Proposition 19 changed the rules for passing property to children, capital gains exposure on a house bought in the 1970s can be enormous, and the order you do things in matters. Helping older adults and their families work through exactly that is the core of my practice, and I have done it hundreds of times. You can book a call with me for a straight conversation about your options, or read through my approach to preparing and selling a home if you are further along in your thinking.