Offered for sale for the first time is 16244 Kennedy Road, a stunning custom-built 5 bedroom, 3 bath residence on a rarely available level lot with ample space for an ADU. Nestled in one of Los Gatos' most desirable settings, this home blends timeless design with exceptional outdoor living. 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 an 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 beautiful grounds include a sparkling pool, sprawling lawn, orchard, and a massive deck. 5 plus car parking, including 3 car garage. Minutes to vibrant downtown Los Gatos shops and restaurants, hiking, biking, top-rated school and transportation.