Shannon Road

Shannon Road and Kennedy Road run east and south out of the Los Gatos town center into the foothills, and the residential streets off them make up one of the more sought after parts of town. It is worth being clear 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, so when people use the names together they generally mean the foothill residential ground on the east side of town, above Blossom Hill Road.

Shannon and Kennedy Homes and Lots

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 1950s and 1960s ranch homes on the lower streets to substantial custom builds higher up, with a steady pattern of older houses being expanded or replaced as land values have risen. There is very little attached housing here.

Between the two roads sits nearby Surrey Farms, a pocket of mostly level ranch lots along Longmeadow and Marchmont that gives buyers the address without the steepest grades. Higher up Kennedy and Shannon, driveways lengthen, lots run to an acre or more and some properties sit outside town limits in unincorporated county land, which affects permits and services.

Parks, Trails and Open Space

Belgatos Park, at the end of Belgatos Road off Blossom Hill Road, has about 17 acres of oak woodland with two miles of trails, and Blossom Hill Park between Shannon and Blossom Hill Road has tennis courts, a ball field and lawns. For longer hikes, the Kennedy Trail into Sierra Azul Open Space Preserve starts from a small roadside lot on Kennedy Road, and it climbs steeply.

Flat walking, which the hills do not provide, is a short drive away at Vasona Lake County Park and Oak Meadow Park, which connect to the Los Gatos Creek Trail. Downtown Los Gatos, with Santa Cruz Avenue restaurants and the library, is a few minutes down the hill.

Schools Serving Shannon and Kennedy

Most of the area runs through Los Gatos Union School District, with Blossom Hill Elementary and Fisher Middle commonly serving the lower streets, and the Los Gatos-Saratoga Union High School District for Los Gatos High. In the foothills the boundaries get irregular and some parcels fall to other districts, such as Loma Prieta Joint Union up the hill, so I verify assignment on every listing rather than relying on the address.

Wildfire and Insurance in the Foothills

Anyone buying or selling in these hills should understand the fire insurance picture, which has changed a lot in recent years for properties in and near wildland areas. Many parcels here sit in mapped fire hazard severity zones, which you can check by address on the state’s fire hazard severity zone maps. 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. My primer on living with wildfires covers defensible space and the disclosures that come with it.

Is Shannon and Kennedy a Good Fit for Downsizers?

For my clients the 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 difficult place to be in your eighties, and nearly every errand means a drive. 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. Some lower streets do have single story ranch homes on level lots, but anyone wanting a condo or townhome usually ends up in places like Rinconada Hills on the west side of town.

The town’s senior services program runs out of the Adult Recreation Center at 208 East Main Street with LGS Recreation, and El Camino Health’s Los Gatos Hospital on Pollard Road and Good Samaritan Hospital in San Jose are both a reasonable drive. If you are 55 or older, Proposition 19 lets you carry your property tax base to a replacement home anywhere in California, which makes a move within Los Gatos more affordable than people assume.

The Shannon and Kennedy Housing Market

Redfin’s Shannon neighborhood logged only one sale in the most recent quarter, which is too thin to mean much, so the 95032 ZIP code is the better gauge. For the three months ending September 2026, 95032 had a median sale price of about $2.27 million, down about 1 percent from a year earlier, with a median of 25 days on market, according to Redfin’s 95032 market data. Los Gatos as a whole sat near $2.44 million over the same stretch.

Foothill properties vary far more than any median suggests, since views, usable land, access and insurability drive value as much as square footage. Two houses of the same size on the same road can sell a million dollars apart, and my guide to living in Los Gatos covers the wider market.

Frequently Asked Questions About Shannon and Kennedy

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. Working through it with older adults and their families, from the tax picture to the timing of a move, is my full time practice. Book a call with me for an honest assessment of your home and your options.