Offered for sale for the first time is 16244 Kennedy Road, a stunning custom-built 5 bedroom, 3 bath residence nestled in one of Los Gatos' most desirable settings. The inviting entry opens to a spacious living room with vaulted ceilings, lovely center fireplace, setting the tone for the home's blend of comfort and elegance. A beautiful formal dining room with French doors flows seamlessly to a elegant brick patio, perfect for dining and entertaining. The expansive kitchen features a central island, skylight, and generous eating area, while the adjacent family room is highlighted by a striking adobe-style fireplace. The main level also offers a versatile office/bedroom, workout room, and a full bath. Upstairs, the primary suite boasts a private balcony, walk-in closet, and a large bath. Three additional bedrooms, one with direct access to a large balcony, and another full bath complete the upper level. The grounds are exceptional, featuring a sparkling pool, sprawling lawn, orchard with room for a tennis court or ADU, and a massive deck, all set on a rarely available level lot. This remarkable property combines timeless design with extraordinary outdoor living. Minutes to vibrant downtown Los Gatos shops and restaurants, hiking, biking, top-rated schools, and transportation.