Shannon Road

Shannon Road and Kennedy Road run south and east out of downtown Los Gatos into the foothills, and the residential streets off them make up one of the more sought after parts of town. It is worth being straight that this is not one formally named neighborhood. Shannon and Kennedy are two separate roads with their own distinct pockets, and listing sites draw them as separate areas. People use the names loosely, and what they generally mean is the foothill residential ground above downtown on the eastern side.

The character comes from the terrain. Streets climb, lots grow as you go up, and houses sit among oaks with views back over the valley. The housing is mostly detached single family, running from mid century homes to substantial custom builds, with a steady pattern of older houses being expanded or replaced as land values have risen. There is very little attached housing here.

For my clients that topography is the whole conversation. A hillside house with a sloped driveway, an entry up a flight of steps and living space spread across levels is a wonderful place to raise a family and a genuinely difficult place to be in your eighties. I have had this conversation many times in these hills, and the households that handle it best are the ones that start planning while the decision is still theirs to make rather than after a fall or a diagnosis forces it.

The compensation is real: quiet, space, trees, and views you cannot buy on the valley floor. Downtown Los Gatos is a few minutes down the hill, with Santa Cruz Avenue restaurants, the Los Gatos Public Library and the town’s senior services program at the Adult Recreation Center on East Main. LGS Recreation runs classes and trips for the 55 and over crowd jointly with Saratoga.

Flat walking, which the hills do not provide, is a short drive away at Vasona Lake County Park and Oak Meadow Park, connecting to the Los Gatos Creek Trail. For trails with more elevation, the open space in the hills above town is right outside the door. El Camino Health’s Los Gatos Hospital on Pollard Road is the nearest emergency room.

Schools run through Los Gatos Union School District and the Los Gatos-Saratoga Union High School District, though in the foothills the boundaries get irregular and some parcels fall outside the town districts entirely. I verify assignment on every listing here rather than relying on the address.

Anyone buying or selling in these hills should also understand the current fire insurance picture, which has changed substantially in recent years for properties in and near wildland areas. It affects what a buyer can obtain and therefore what they will pay, and it is better handled early in a sale than discovered during escrow.

On price, Los Gatos ran a median sale of about $2.7 million through the summer of 2026, up roughly six and a half percent year over year, with a median of around 23 days to contract. Foothill properties vary far more than that median suggests, since views, usable land, access and insurability drive value as much as square footage. My Los Gatos home prices page tracks the trend and the full Los Gatos area guide covers the rest of town.

If you are in a hillside house and starting to wonder how many more years it works, that is a good conversation to have early rather than late. Proposition 19 lets homeowners 55 and over carry their property tax basis to a replacement home anywhere in California, which makes staying in Los Gatos more affordable than people assume. Working through that with older adults and their families is my full time practice. Book a call with me for an honest assessment, or read how I prepare and market a home.