Kennedy East, Los Gatos, CA

Tucked into the oak-studded foothills south-east of downtown Los Gatos, this long, narrow enclave follows the spine of the ridgeline. Homes sit on generous parcels, many terraced into the slope to frame sweeping valley or canyon views. Architecture skews toward custom Mediterranean and wine-country farmhouse styles, with the occasional contemporary retreat hidden behind gates and mature trees. Weekend recreation revolves around the Kennedy Trailhead, a popular entry into Sierra Azul Open Space that starts inside the neighborhood, plus several boutique vineyards where residents can book tastings or pick up a local bottle. Everyday conveniences are limited, so groceries, cafés, and schools all require a short drive back into Los Gatos proper. Roads are winding and shoulder-less, trading walkability for serenity and dark-sky nights. Life here feels equal parts country and luxury, appealing to those who value privacy, acreage, and trail access over quick commutes or bustling sidewalks. Expect wildlife sightings and magnificent sunsets, alongside the practical considerations of hillside living such as fire-season prep and narrow driveways.