Shepherdstown Homes for Sale

Shepherdstown Homes for Sale

Welcome to Shepherdstown, West Virginia—a charming town steeped in history and natural beauty. Nestled along the banks of the Potomac River in Jefferson County, Shepherdstown is the oldest town in West Virginia, boasting a rich heritage that dates back to 1734. This picturesque community offers a unique blend of small-town charm and vibrant cultural experiences, making it an ideal place to call home.

As you stroll through the tree-lined streets, you'll discover beautifully preserved historic buildings, quaint shops, and delightful eateries that reflect the town's artistic spirit. The annual events, such as the Shepherdstown Street Fest and the Contemporary American Theater Festival, bring the community together and celebrate local talent. Outdoor enthusiasts will appreciate the nearby hiking trails, parks, and the scenic river, perfect for kayaking and fishing.

When it comes to real estate, Shepherdstown offers a diverse selection of homes for sale, catering to various lifestyles and preferences. Whether you're looking for a cozy cottage, a spacious family home, or a charming historic residence, you'll find it here. Many properties feature stunning views, lush gardens, and easy access to local amenities, ensuring that you can enjoy both comfort and convenience.

With its welcoming atmosphere, vibrant arts scene, and rich history, Shepherdstown is more than just a place to live—it's a place to thrive. Explore the homes for sale in this enchanting town and discover the perfect backdrop for your next chapter. Your dream home awaits in Shepherdstown!

Newest Shepherdstown Homes for Sale

$649,900
4 Beds ⋅ 3 Baths ⋅ WVJF2025658 MLS
**Refined Country Living in Historic Shepherdstown** Experience the perfect balance of luxury, privacy, and timeless charm at 277 Shveda Way. Set on 1.82 beautifully landscaped acres just minutes from the heart of historic Shepherdstown, this exceptional ranch residence offers sophisticated one-level living in one of West Virginia's most sought-after locations. Thoughtfully designed for both elegant entertaining and everyday comfort, the open-concept floor plan is filled with natural light and seamlessly connects the living, dining, and kitchen spaces. The main level features three generously sized bedrooms and two full bathrooms, creating a comfortable and functional layout, while a private fourth-bedroom suite with its own full bath is tucked above the garage. This secluded space is perfectly suited for overnight guests, multigenerational living, an executive home office, an au pair suite, or a quiet retreat, offering exceptional flexibility while maintaining privacy from the main living areas. The expansive walkout basement presents an extraordinary opportunity to create additional luxury living space tailored to your lifestyle. Envision a custom home theater, wine cellar, fitness studio, game room, or guest quarters—the unfinished lower level provides a blank canvas with endless possibilities while adding significant long-term value. Outside, nearly two acres of beautifully tree-lined grounds create an idyllic setting for outdoor entertaining, gardening, or simply enjoying the peace and privacy of your own estate-like setting. Beyond the property, discover the unmatched lifestyle that has made Shepherdstown one of the Mid-Atlantic's most cherished destinations. Stroll charming streets lined with boutique shops, acclaimed restaurants, art galleries, and inviting cafés. Enjoy live theater, farmers markets, festivals, and the cultural influence of Shepherd University, or spend weekends exploring the scenic Potomac River, nearby wineries, golf courses, and miles of outdoor recreation. Ideally located for commuters while offering the serenity of country living, 277 Shveda Way provides convenient access to Martinsburg, Charles Town, Maryland, Northern Virginia, and Washington, D.C. Whether you're seeking a full-time residence or a sophisticated weekend escape, this remarkable property delivers an exceptional combination of quality, versatility, and location. Rarely does a home offer this blend of refined craftsmanship, flexible living spaces, an estate-sized homesite, and proximity to one of West Virginia's most celebrated historic towns. **277 Shveda Way is more than a home—it's an invitation to experience a lifestyle defined by elegance, tranquility, and enduring appeal.

277 Shveda Way, Shepherdstown
$285,000
3 Beds ⋅ 1 Baths ⋅ WVJF2025646 MLS
Unique Mixed-Use Opportunity! Rare corner lot offering residential, light industrial, and commercial zoning, providing exceptional flexibility for homeowners, investors, or business owners. The property features a cozy home ready for comfortable living along with a spacious shed ideal for storage, a workshop, or hobby space. High-visibility location with convenient access to Shepherdstown, Martinsburg, and major commuter routes. Whether you're looking for a live-work property, investment opportunity, or a site with future potential, this versatile property offers endless possibilities. Don't miss your chance to own this one-of-a-kind property with multiple permitted uses in a desirable location. Schedule your private showing today!

7628 Martinsburg Pike, Shepherdstown
$560,000
4 Beds ⋅ 3 Baths ⋅ WVJF2025516 MLS
This well-maintained rancher built in 2018 is completely move in ready and situated on 2 private acres in Shepherdstown off Persimmons Lane. Offering 4 bedrooms and 3 full bathrooms, this home features an open floor plan with cathedral ceilings, creating a bright and spacious feel centered around a cozy fireplace—perfect for relaxing or entertaining. The well-appointed kitchen offers granite countertops, stainless steel appliances, and a convenient eat-in dining area, while a separate formal dining room provides the perfect space for hosting family gatherings. The updated primary suite is a true retreat, featuring a beautifully renovated bath and an oversized walk-in closet. A unique loft suite offers flexible space for guests, a home office, or a private getaway. The full walk-out basement provides abundant storage and endless possibilities for future finished living space. Additional updates include master bedroom and bathroom, new luxury vinyl plank flooring, new sliding glass door and a whole-house water treatment system for added peace of mind. Combining modern finishes, functional living space, acreage, and a sought-after location, this property truly offers the versatility today's buyers are looking for. Home inspection already done for buyers' convenience, some items have been repaired, septic recently pumped/inspected, check documents for inspection and invoice.

50 Lamar Ln, Shepherdstown
$400,000
3 Beds ⋅ 3 Baths ⋅ WVJF2025616 MLS
Welcome to 207 Sandpiper Lane, a beautifully maintained, like new, 3-bedroom, 3-full-bath home situated on nearly one acre in desirable Shepherdstown, West Virginia. Built in 2018, this inviting property offers a thoughtful layout with generous living space and a fully finished walkout lower level. The main level offers an open floor plan, hardwood floors in the main living areas, a spacious living room, kitchen and dining area with access to the deck. The primary bedroom includes a full private bathroom. Two more nice size bedrooms and a 2nd full bathroom round out the main level. The lower level includes a spacious recreation room, 3rd full bathroom, laundry room and a door leading to the backyard. The home features a two-car side-load garage, adding both convenience and attractive curb appeal. You'll love entertaining on the 12' x 16' rear deck overlooking the beautiful backyard that backs to mature trees, creating a peaceful and private setting for relaxing and enjoying the outdoors. Conveniently located near historic charm of downtown Shepherdstown, this home offers the ideal combination of space, privacy, modern construction, and accessibility. Don’t miss the opportunity to make this exceptional Shepherdstown property your own!

207 Sandpiper Ln, Shepherdstown
$749,000
3 Beds ⋅ 3 Baths ⋅ WVJF2025332 MLS
This is a unique Home On 3+ Private Acres Located Just 2 Miles From The Public Boat Ramp To The Potomac River In Shepherdstown, WV. This 3 Bedroom, 3 Bath Home Spread Over 2 Floors Sitting On A Hill Outside Shepherdstown With Beautiful Sunrise And Sunsets. Six Years Young...Windows, Doors, Electrical, Plumbing, HVAC, Spray Foam Insulation, Drywall, Floors, Lighting, Oversized Fans, All Appliances And More! Craftsman FinishesThroughout, Glass Transoms, Solid Doors, 12' Slider, Chef's Kitchen, Open Floor Plan, Tiled Bathrooms and Showers, EV ChargePoint Fast Charger And Much More...Bring Your Wife, Her Horse, Bring Your Bow, Bring Your Fishing Kayak, Don't Forget The Kids! Carport Is Large Enough For An RV. This Large Comfortable Home With Several "Flex Spaces" Offers A Great Place To Raise A Family Within 60 Miles Of DC , Baltimore And Much Of Northern VA.

92 Fidlers Way, Shepherdstown
$597,000
4 Beds ⋅ 4 Baths ⋅ WVJF2025190 MLS
Welcome to 262 Canal Way, Shepherdstown, WV, where thoughtful upgrades and an exceptional location come together in one beautiful home. Nestled in one of Shepherdstown's most desirable neighborhoods, this spacious residence offers the perfect blend of elegance, comfort, and functionality. Step inside to find beautiful hardwood floors flowing throughout the main living areas, creating a warm and inviting atmosphere. The open-concept design is ideal for both everyday living and entertaining, centered around a gourmet kitchen featuring an oversized center island, double wall ovens, abundant cabinetry, and generous prep space. Comfort-height kitchen and bathroom countertops add a touch of luxury and convenience throughout the home. Upstairs, the private primary suite serves as a peaceful retreat, complete with a spacious en suite bathroom and generous walk-in closets, offering comfort, privacy, and ample storage. Additional bedrooms provide flexible space for family, guests, or a home office. The finished lower level expands the home's versatility with a stunning floor-to-ceiling stone fireplace that creates a warm, cozy gathering space. A wet bar rough-in is already in place, making it easy to design the entertainment area of your dreams—whether it's a game room, media room, home gym, or guest suite. Thoughtful details throughout the home include ceiling fans in most rooms, a central vacuum system for added convenience, and quality finishes designed for comfortable everyday living. Major updates—including a roof replaced in 2020 and an HVAC system replaced in 2021—provide added value and peace of mind for years to come. Located just minutes from historic downtown Shepherdstown, you'll enjoy easy access to charming boutiques, award-winning restaurants, coffee shops, parks, walking trails, the Potomac River, and the C&O Canal Towpath. Convenient commuter routes to Charles Town, Martinsburg, Maryland, and Northern Virginia make this location as practical as it is picturesque. Beautifully maintained, tastefully upgraded, and ideally located, 262 Canal Way offers the opportunity to enjoy everything that makes Shepherdstown one of the Eastern Panhandle's most sought-after places to call home. Schedule your private showing today and experience it for yourself.

262 Canal Way, Shepherdstown
$425,000
3 Beds ⋅ 1 Baths ⋅ WVJF2024878 MLS
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
$575,000
4 Beds ⋅ 4 Baths ⋅ WVJF2024806 MLS
Move In Ready, 4 bed, 3.5 bath Farmette on 2.25 Unrestricted acres in Shepherdstown. This home has many updates including a NEW ROOF, 2 New HVAC Units, New Hot Water Heater, New bathrooms with custom tile and quartz tops, New LVP flooring, fresh paint from top to bottom, New hardware and fixtures. The brand new kitchen features stainless steel appliances and quartz counter tops. Other features include: 3 bedrooms on the upper level, and 1 bedroom/home office on the main level, a front and rear covered porch, an oversized 2 car garage, a barn, and a fully finished basement.

637 Persimmon Ln, Shepherdstown
$635,000
4 Beds ⋅ 3 Baths ⋅ WVJF2024712 MLS
Set on 4.07 acres just minutes from downtown Shepherdstown, this spacious home offers room to spread out, a peaceful setting, and the opportunity to make it your own. A covered front porch leads into a well-designed main level with formal living and dining rooms featuring hardwood floors, a comfortable family room with built-in shelving and a wood-burning fireplace that is currently capped, a private office or bonus room filled with natural light, and a generously sized mudroom and laundry area with wash sink and built-in cabinetry that adds everyday function. The eat-in kitchen is clean and well maintained in its original condition, offering a solid starting point for future updates. All four bedrooms are located upstairs, including a primary suite with its own bath, while three additional bedrooms share a full hall bath. An unfinished basement provides excellent storage and room for expansion over time. Recent improvements include a new roof in 2025 and a newer HVAC system installed within the past few years. Outside, the in-ground pool is not currently operational but remains in place for a buyer who wants to restore it or redesign the outdoor space. With acreage, established neighborhood appeal, and close proximity to Shepherdstown, this property offers a rare combination of space, setting, and long-term potential.

185 Shepherd Ln, Shepherdstown
$439,000
3 Beds ⋅ 2 Baths ⋅ WVJF2024604 MLS
Charming Country Retreat nestled on a peaceful 1.63-acre private parcel along a quiet country road just outside historic Shepherdstown, this inviting 1963-built home offers the perfect blend of timeless character and versatile living space. With approximately 2500 total square feet, 3 bedrooms, and 2 bathrooms, this single-family residence sits on unrestricted land—ideal for those seeking freedom and flexibility in the Eastern Panhandle. Step inside to discover lovely hardwood flooring that flows throughout the main living areas, creating a warm and welcoming atmosphere. The spacious layout is filled with natural light and provides ample room for comfortable everyday living and entertaining. The finished basement presents exciting possibilities—easily transform it into a fourth bedroom, a creative hobby room, home office, or additional living space to suit your lifestyle. Outside, the property truly shines as a gardener's and nature lover's paradise. It's loaded with mature fruit trees, berry bushes, and an abundance of trees that provide privacy, shade, and seasonal beauty. A private deck off the back offers a serene spot to relax, enjoy the views, or entertain family and friends while surrounded by your own personal woodland setting. Conveniently located near Shepherdstown's vibrant arts scene, dining, and amenities, yet tucked away for privacy, this home is a rare find for those who appreciate country living with easy access to everything the area has to offer. Whether you're looking for a peaceful primary residence, a hobby farm setup, or a versatile property with room to grow, 561 Billmyer Mill Road delivers endless potential.

561 Billmyer Mill Rd, Shepherdstown
$515,000
4 Beds ⋅ 4 Baths ⋅ WVJF2024326 MLS
As soon as you enter this beautiful home you realize this is a well maintained one! Nice open stairway and two-story foyer to the second floor. Sparkling wood floors and laminate floors as well. First floor offers living room as well as a family room off the kitchen. Formal dining but breakfast room also and, counter seating in a beautifully laid out kitchen. Granite counters, gas stove, built in microwave, oversized refrigerator and matching dishwasher. Breakfast room has lots of windows and wonderful sunlight coming in. Dark laminate floor flows nicely and easy clean. Only steps away to a large paved patio area and wrought iron fenced backyard. Yard backs to one of the common areas, allowing nice privacy in the rear as well as additional play yard! All four of the upstairs bedrooms are carpeted. Primary bedroom is extra large with an ensuite bath with separate tub and shower. The primary bedroom closet has custom built- in shelving. Another bath off the other 3 bedrooms rounds out the second floor. Downstairs finds a large finished area which could be playroom, office, hobby or even an extra bedroom. A half bath services that area and an outside walkup entrance. Lots of updated lighting and ceiling fans. New roof in 2025, new HW heater, 8 yr. old heat pump, and paneled garage door! Guardian alarm system and Ring cameras. Minutes to the grocery store, pharmacy, gas stations and restaurants! 5 minutes from downtown historic Shepherdstown and Shepherd University (walking/biking path to Shepherd in the neighborhood!) Be at the Antietam Battlefield in 10 minutes and Harpers Ferry in 20 minutes. And, lots of outdoor activities from hiking, and fishing and boating on the Potomac River.

65 Maddex Farm Drive, Shepherdstown
$420,000
3 Beds ⋅ 3 Baths ⋅ WVJF2024250 MLS
Main level living never looked so easy in this newly renovated and move-in ready contemporary home in the desirable Maddex Farm community with its connecting pathways to the town and University. Brand new architectural shingle roof, freshly painted with hardwood floors, and new carpet in the bedrooms and luxury vinyl tile in the bathrooms - this home has been renovated on all levels, inside and out! The hybrid floor plan features an updated kitchen space with brand new appliances, connecting to an open dining and family room with beautiful vaulted ceilings, a balcony overlook, and a sliding glass walkout to the refinished deck and private backyard. There's a primary bedroom and bathroom suite on the main floor and two guest bedrooms, with cubby hole storage, that share a guest bath upstairs. A finished walkout basement provides great versatility with an additional half bathroom and flexible living space. A HUGE storage room highlights the lower level. This original section of the Maddex Farm community has great accessibility to all Shepherdstown offers with mature landscaping and shade trees.

122 Hensel Dr, Shepherdstown
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