Exceptional opportunity in the heart of Healdsburg's historic district - just three blocks from the Plaza. This rare property features two separate homes plus two detached accessory spaces on an ~8,060 SF lot, offering incredible flexibility for multi-generational living, rental income, or a primary residence with guest accommodations. The front home (circa 1939) has been thoughtfully restored, blending timeless character with modern updates. Period details such as coved ceilings, archways, and hardwood floors are complemented by a renovated kitchen, updated windows, and a beautifully preserved vintage bath. A detached studio with full bath and an attached garage add versatility. The newer rear bungalow (built 2010) offers a bright, open-concept layout with 9-foot ceilings, abundant natural light, and seamless indoor-outdoor flow. Features include a well-appointed kitchen, gas fireplace, heated bathroom floors, and its own detached accessory room - ideal for a home office, studio, or guest overflow. Both residences enjoy private outdoor spaces with mature landscaping, patios, grape arbors, and fruit trees, creating a peaceful compound setting just moments from world-class dining, tasting rooms, and the vibrant Healdsburg Plaza. A unique blend of historic charm and modern convenience in an unbeatable in-town location.