Just two blocks from the vibrant Shepherdstown Historic District and set along the quiet tree-lined street of Fairmont Avenue, this charming brick colonial offers a rare and compelling balance: immediate access to the character, walkability, and charm of historic Shepherdstown—while enjoying the flexibility and ease of living just outside the district’s formal guidelines. Beyond the main residence, a detached structure with additional full bathroom and bedroom currently operating as a successful Airbnb, offers turnkey potential for a short or long-term rental. With 4 bedrooms and 3 full baths, the home blends timeless character with thoughtful, modern updates. Most of the original hardwood floors have been recently refinished, enhancing the warmth and continuity throughout. A newly added main-level bath, finished with a beautifully lime-washed wall, brings both style and functionality to the first floor. A slate-tiled foyer welcomes you inside and flows seamlessly to a private screened-in porch, creating an effortless connection between indoor and outdoor living. The main level offers a classic, circular layout ideal for both daily life and entertaining. The living room is rich with character, featuring wood paneling, arched built-ins, and a large picture window that draws in natural light and garden views. A dedicated dining room transitions into the kitchen and family room, forming a comfortable, open gathering space. Upstairs, four well-proportioned bedrooms and two full baths provide a peaceful retreat, anchored by an oversized primary suite with its own ensuite bath and walk-in closet. A large attic offers exceptional additional storage. The lower level provides usable footprint and storage consistent with the home’s original structure, adding further flexibility. Outdoors, a cozy garden and spacious yard create space for relaxation, entertaining, and play. A rear lean-to structure includes additional garden storage, thoughtfully tucked into the landscape. Beyond the main home, a fully renovated detached cottage—approximately 800 sq ft and completed in 2025—adds exceptional versatility and value. Equipped with energy-efficient mini-split systems to help manage utility costs, this separate dwelling includes a full kitchen, living space, bedroom, and full bath. It is currently operating as a savvy income-generating Airbnb, offering immediate revenue potential or flexibility for guests, extended family, or private workspace. Additional upgrades include a whole-home water treatment system featuring dual filtration and UV purification, as well as an advanced ozonator laundry system designed to reduce or eliminate the need for detergent—enhancing both efficiency and sustainability. The home also features two fireplaces, one of which is currently covered, preserving its character while offering future optionality. Located just moments from the heart of Shepherdstown, you’re within easy walking distance to schools, shops, restaurants, and everyday essentials, as well as the charm of German Street and the surrounding community. Here, you can enjoy the architectural richness and lifestyle of a historic town—without the added layer of oversight—making this an especially rare opportunity in one of West Virginia’s most beloved communities.