Tucked behind the iconic Sebastiani Cherry Block vineyard, this extraordinary Sonoma Valley estate blends classic design with resort-style living just minutes from the Plaza. Set on five oak-studded acres, the property offers exceptional privacy and scale in one of wine country's most desirable locations. At the heart of the approx. 12,000 sq ft residence is a breathtaking formal living room with soaring ceilings, detailed millwork, and the ambience of a grand library. The home unfolds around this central space with a chef's kitchen clad in Breccia Medicea stone, a Le Cornue range, dining for 20, formal and casual gathering rooms, a media/game lounge, two powder rooms, and flexible guest spaces including a den with fireplace that can serve as a fifth bedroom. Upstairs, the primary suite captures panoramic vineyard and mountain views and features dual stone-clad baths, two walnut dressing rooms, a gym, and fireside sitting area. The insulated lower level includes a tasting room, office, and prep kitchen ideal for a wine cellar or expanded entertaining. Outside, flat, usable land offers potential for tennis, bocce, or a collector's car barn. A rare, legacy estate pairing timeless architecture with room to grow.