A rare find: gated privacy + acreage + views + guest house in Los Gatos. Set on ~21.6 acres - panoramic views, your own trails, and true resort-style living - minutes to Skyline adventures and an easy drive to downtown Los Gatos. The 3083 sf main residence with nearly 700 sf of bonus space is wrapped in windows with soaring ceilings and deck-to-view entertaining, complemented by a 480 sf guest house with 300 sf of accessory structures for visitors, income, or work from home flexibility. Showpiece smart chef's kitchen with premium appliances, dual beverage fridges, and radiant-heat floors. Property amenities include a producing orchard, fenced garden, wine cellar, vineyard-ready soil, solar power with backup generator, bocce/petanque court, detached two-car garage (642 sf), abundant parking, private trails, and multiple outdoor entertaining areas. An exceptional opportunity for a private mountain retreat, vineyard compound, or legacy estate offering rare seclusion with convenient proximity to Los Gatos and Silicon Valley.