Rare opportunity in the heart of St. Helena! This historic 1910 property offers exceptional versatility and charm, featuring two residences plus a detached studio guest cottage, all thoughtfully updated while preserving its timeless character. The main homes include a spacious 3BD/2BA and a well-appointed 2BD/2BA, each with separate entrances, making this an ideal setup for multi-generational living, extended family, or income-producing opportunities. Inside, the homes showcase beautiful hardwood floors, abundant natural light, and an inviting open beam great room that highlights the property's historic appeal. Modern updates throughout provide comfort and functionality while maintaining the warmth and character of the original design. Each living space offers privacy and flexibility, allowing for a variety of living arrangements or rental configurations. The detached studio cottage, complete with its own kitchen and full bathroom, adds even more value and potentialperfect for guests, a home office, or additional rental income. With three distinct living spaces across two structures, this property presents a rare chance to own a true compound in one of Napa Valley's most desirable locations. Set in a peaceful and serene environment, the property is just steps from downtown St. Helena, offering easy access to world-class dining, renowned wineries, boutique shopping, local markets, and top-rated schools. Whether you're seeking a primary residence, a second home with income potential, or a long-term investment, this unique property combines lifestyle, location, and opportunity in the heart of Wine Country.