Located in the heart of the Paso Robles Wine Trail within the highly sought-after Paso Robles Willow Creek District AVA, this exceptional 20+- acre offering presents a rare opportunity to own a legacy property with both history and income-producing potential. Set atop the rolling landscape, the Italian Villa-style main residence enjoys a commanding southwest-facing position overlooking expansive, plantable soils ideal for vineyard development. Built in 2007, the primary residence offers approximately 3,200+- square feet with 4 bedrooms and 4 bathrooms, thoughtfully designed with an open layout, well-appointed kitchen, and multiple indoor and outdoor living spaces that capture the surrounding vineyard and hillside views. The property is currently a county-registered vacation rental with a strong and established income history, offering immediate usability for a buyer seeking both lifestyle and investment. Below the main residence, the original homestead, built in 1925, provides a second dwelling with 3 bedrooms and 2 bathrooms, rich in character and history. Surrounding improvements include a large shop/garage, orchards, and a chicken house and garden area, creating a setting well-suited for a homesteader or those seeking a self-sustaining lifestyle rooted in the land. Positioned along Vineyard Drive on the premier Westside 46 corridor, the property offers a uniquely private setting nestled among renowned vineyards, including Denner and Jada. The combination of elevated homesite, usable acreage, and existing infrastructure provides versatility for vineyard development, multi-generational living, or continued income use. With proximity to world-class wineries and just a short drive to downtown Paso Robles, this offering embodies the essence of Central Coast living--where heritage, land stewardship, and long-term value converge.