Nestled in the heart of Brentwood, this reimagined Craftsman residence blends timeless character with modern sophistication across two full-scale residences. Thoughtfully remodeled, the property encompasses nearly 3,200 square feet of total living space, including a stunning main home and a fully detached, two-level Accessory Dwelling Unit (ADU) -- each with its own private outdoor setting and remodeled interiors. A charming covered front porch welcomes with signature Craftsman detailing, leading into an elegant main residence of nearly 2,000-square-feet. Inside, natural light pours through shuttered windows, illuminating honey-toned hardwood floors, crisp white walls, and crown moldings that convey both polish and warmth. The spacious living room, anchored by a classic fireplace, flows effortlessly into the formal dining area and bright kitchen featuring quartz countertops, custom cabinetry, and Thor stainless steel appliances. Sliding glass doors open to a sun-drenched cedar deck and expansive grassy lawn, framed by privacy fencing -- creating a tranquil setting for outdoor entertaining or everyday enjoyment. The first-floor primary suite is a serene retreat with a walk-in closet and spa-caliber bath, including dual vanities, a soaking tub, and a glass-enclosed shower. A powder room and stacked laundry closet complete the main level. Upstairs, two additional bedrooms offer peaceful treetop views and relaxed, natural light. Set at the rear of the property, the 1,200+ square-foot detached ADU offers exceptional flexibility for extended guests, work-from-home, or income potential. With a private entrance, the ADU spans two levels and features an open-concept living space, full kitchen, in-unit laundry, and attached 2-car garage. The main level opens to a hedge-lined yard with its own cedar deck, while upstairs two ensuite bedrooms with vaulted ceilings are complemented by a third ground-floor bedroom, offering versatility and comfort. Ideally positioned moments from San Vicente Boulevard's boutiques, cafes, and acclaimed restaurants, and in close proximity to Brentwood Country Club, the local farmer's market, and top-rated schools, this exceptional property presents a rare dual-residence opportunity in one of the Westside's most desirable neighborhoods -- offering both lifestyle and long-term value.