Shepherdstown Real Estate

Shepherdstown Real Estate

Welcome to Shepherdstown, West Virginia—a charming community steeped in history and nestled along the banks of the Potomac River. As one of the oldest towns in West Virginia, Shepherdstown boasts a rich heritage that dates back to the late 18th century, providing a unique blend of historic charm and modern amenities.

This picturesque subdivision is renowned for its vibrant arts scene, cozy cafes, and boutique shops that line the quaint streets. Residents and visitors alike are drawn to the historic architecture, including the iconic Shepherdstown Opera House and the beautifully preserved homes that reflect the town’s storied past. The community is also home to Shepherd University, which adds a youthful energy and a variety of cultural events throughout the year.

Nature enthusiasts will find plenty to love about Shepherdstown, with its proximity to the beautiful Appalachian landscapes. Outdoor activities abound, from hiking and biking along the scenic C&O Canal Towpath to kayaking on the Potomac River. The nearby Antietam National Battlefield offers a glimpse into American history, making it a perfect spot for history buffs and nature lovers alike.

Shepherdstown is not just a place to live; it’s a lifestyle. With its friendly community atmosphere, excellent schools, and a calendar full of local events, you’ll find that this charming town is the perfect place to call home. Whether you’re looking for a quiet retreat or an active lifestyle, Shepherdstown welcomes you with open arms and endless possibilities. Discover your new beginning in this enchanting subdivision where history and modern living harmoniously intertwine!

Newest Listings in Shepherdstown

$425,000
3 Beds ⋅ 1 Baths
Charming home just outside of town limits. Walking distance to downtown Shepherdstown with convenient access to local restaurants, shops, parks, and the University. This residence features a welcoming atmosphere with spacious living areas, abundant natural light, and lots of character. Enjoy outdoor living with a beautiful back yard and mature landscaping. Close to commuter routes while maintaining the charm and tranquility of one of West Virginia's most sought-after historic communities.

17 Old Prospect Ave, Shepherdstown

Listing courtesy of Path Realty. Contact: 3042796950
$850,000
4 Beds ⋅ 3 Baths
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.

22 Fairmont Ave, Shepherdstown

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

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