Experience the very best of Wine Country living at this exceptional hillside retreat, privately nestled on approximately 1.51 acres in Sonoma's highly sought-after Diamond A community. Surrounded by majestic oaks, beautifully landscaped grounds, and sweeping views across Sonoma Valley toward the Mayacamas Mountains, this one-of-a-kind property offers a rare blend of architectural character, flexibility, and resort-style outdoor living. Designed to embrace its spectacular setting, the residence welcomes you with soaring vaulted wood-beamed ceilings, expansive walls of glass, and light-filled living spaces that seamlessly connect indoors and out. The dramatic great room, anchored by a striking fireplace, flows into the beautifully updated kitchen featuring quartz countertops, stainless steel appliances, abundant cabinetry, generous prep space, and an oversized peninsula perfect for gathering. The adjoining dining room is surrounded by windows framing lush gardens, the sparkling pool, and picturesque valley views. The main residence is currently configured with four bedroom spaces, three full bathrooms, one half bath two laundry areas, multiple living areas, two dedicated office areas, a well-appointed main kitchen, and an additional kitchen, offering exceptional flexibility for today's lifestyle. A separate upper-level retreat features its own spacious living area, full bathroom, vanity, and private deck overlooking the surrounding landscape, creating an ideal space for guests, recreation, or creative pursuits. Adding to the property's versatility is a charming detached guest cottage complete with a living room, bedroom, and bathroom, ideal for visitors, a private office, artist's studio, fitness room, or other flexible uses. Outside, mature specimen trees, colorful gardens, natural stone pathways, multiple entertaining patios, a sparkling pool,and a relaxing spa create a private outdoor sanctuary. Whether entertaining, enjoying morning coffee beneath the trees, or watching spectacular sunsets over the valley, every outdoor space celebrates the beauty of its surroundings. Located just minutes from the Historic Sonoma Plaza, world-renowned wineries, acclaimed restaurants, hiking and biking trails, and the very best of Wine Country, this remarkable Diamond A property presents a rare opportunity to own a private retreat where timeless architecture, flexible living, and an unforgettable setting come together in perfect harmony.