Historic once-in-a-generation 577.65± acre legacy ranch estate just off Highway 58, where California history, presidential winemaking pedigree, and expansive lifestyle opportunity converge. Established in 1900 and formerly owned by Alex Trebek, a pioneer of Paso Robles wine country, the property is internationally recognized for producing wines served at the White House during President George H. W. Bush's first inauguration. Spanning 4 APNs with nearly one mile of highway frontage, the ranch offers rare scale, privacy, and flexibility, with everything in excellent condition and lakes currently full from recent rains. The estate features 22± acres of producing vineyards planted to Syrah, Cabernet Sauvignon, Zinfandel, and Pinot Noir, supported by exceptional production infrastructure including a 9,700± SF winery building with 1,600± SF apartment and 500± SF office, a 10,000± SF barrel room with 3,750± SF expansion, barrel stacking up to five high, and multiple warehouse facilities for case goods and pallet storage. A robust water system includes two productive wells (one producing approximately 150 GPM), six 6,000-gallon storage tanks, and four 2,500-gallon holding tanks, ensuring reliable operations for vineyard, livestock, and hospitality uses. Residential and hospitality improvements total 11 bedrooms and 13 bathrooms across multiple homes and guest accommodations-ideal for a private compound, staff housing, or retreat use. Residences include a Main House (3BD/3BA), Grey House (2BD/2BA), Yellow House (2BD/2BA), Original Yellow House (3BD/2BA), and Green House (3BD/3BA), plus a private Honeymoon Suite (1BD/1BA), a 926± SF game and entertainment room with bath, and additional hosting spaces. Historic barns-once used for weddings, charity functions, and Cal Poly events-add character and functionality for large gatherings. Fully fenced pastures and livestock pens support cattle, horses, sheep, and pigs, while rolling terrain, lakes, and open space invite fishing, riding, ATV use, shooting sports, and recreation. Rare historic elements include the original Highway 58 bridge from its dirt-road era and an original blacksmith shop. With no current Williamson Act or conservation easement (but potential for future designation), this is an extraordinary opportunity as a vineyard estate, equestrian ranch, event venue, retreat, or legacy investment.