Privacy, Hill Country charm, and income potential all just blocks from Fredericksburg's vibrant Main Street. Tucked away on a quiet street with mature landscaping, this versatile property offers a rare combination of location, lifestyle, and opportunity. An expansive covered walkway leads through a main corridor and opens to a private patio, welcoming you into a spacious, light-filled great room featuring living and dining areas centered around a stunning floor-to-ceiling stone gas-log fireplace. With five bedrooms, four baths, two living areas, two kitchens, and two dining spaces, the layout is ideal for multi-generational living or owner-occupancy with income potential. The main living area features an open-concept kitchen with a work island, breakfast bar, breakfast nook, and seamless flow into the formal dining and living spaces. Designed for ultimate flexibility, both residences operate independently with their own private entrances, while remaining discreetly connected via a covered outdoor corridor each with its own locked access and an interior lockable door, allowing owners to effortlessly transition between fully separate living and a unified multi-generational home. The back unit features two private ensuite bedrooms, a hot tub, xeriscaped low-maintenance turf, and additional private parking further enhancing its appeal. With a newly added short-term rental permit licensed for up to 6 guests, it is ready to generate income from day one as a STR, long-term rental, or guest accommodations. The front residence enjoys a beautiful courtyard and shaded garden space, while the back accessory dwelling is accessed privately from the rear of the property. Outdoor living shines with two private cedar-stave enclosed courtyards. A tree-lined concrete driveway leads to the attached two-car garage. All of this just minutes from shopping, dining, wineries, and the heart of downtown Fredericksburg.