Shepherdstown WV Real Estate & Homes for Sale

347 Maddex Drive is the one you have been waiting for. Loved by only 1 owner since it's 2007 build. This beautiful brick front home welcomes you with the quaint sitting area near the front stoop. Hardwood flooring that was refinished a few years ago on almost the entire main level greeting you as soon as you open the front door. BRAND NEW CARPET on the entire upstairs and living room. Freshly painted in many areas throughout! Amazing Kitchen extension giving you ample space to dine and entertain but still providing the formal dining area for a more intimate space. The family room is perfectly positioned in the heart of the home with a gas fireplace sitting center stage accented with a beautiful hearth. The main level flex space is currently used as a second living room but would be the perfect space to setup an office, hobby room, play area, or other uses that may fit your needs. Upstairs provides a great primary suite with cathedral ceiling, double closets, and a bathroom that gives you all the necessities. It offers a large soaking tub, separate stand-up shower, double sinks and private water closet. 3 additional bedrooms share a hall bathroom, all of which offering their own design touch and generous space. Add to your home enjoyment with the partially finished basement with a wet bar stub and media box ready for you to setup the ultimate cave with a fully finished bathroom. Unfinished area has a nice, dedicated gym area off the laundry space. Backyard patio area perfect for those summer BBQ's, Fall Evenings, or a great coffee spot on spring mornings. Let's get your tour scheduled and make this home YOUR next home.

Private Back to Trees Homesite! Walkout Basement and Finished Rec Room! Sits on nearly a 1/3 acre homesite with great views! Complete with a main level bedroom and full bath, great for guests. This 2 Story single family home marries features and affordability and comes with everything included. 5 Bedrooms a 2nd floor loft, LVP floors in the main living spaces, included kitchen appliances, granite countertops and white cabinets give the updated look you've always wanted. Located next to Morgan's Grove Park and just down the street from Downtown Shepherdstown!

Quick Move In! Back to Trees! Located in our Tollhouse Woods community on the edge of Downtown Shepherdstown! This 2 Story single family home marries features and affordability and comes with everything included. 4 Bedrooms, LVP floors in the main living spaces, included kitchen appliances, granite countertops and white cabinets give the updated look you've always wanted. Located next to Morgan's Grove Park and just down the street from Downtown Shepherdstown!

Quick Move In! Walk out Basement w/ finished Rec Room! Located in Downtown Shepherdstown! This property and sits on a flat and spacious homesite, one of the largest in the community! This 2 Story single family home marries features and affordability and comes with everything included. 4 Bedrooms, LVP floors in the main living spaces, included kitchen appliances, granite countertops and White cabinets give the updated look you've always wanted. Located next to Morgan's Grove Park and just down the street from Downtown Shepherdstown!

Welcome to this beautifully maintained all-brick rancher situated on a picturesque one-acre lot surrounded by pastoral and mountain views. Offering two bedrooms and one full bath, this home provides comfortable single-level living in a peaceful rural setting while still being conveniently located. Step outside and discover the propertys standout feature-an impressive, recently built 30' x 48' x 16' top-of-the-line pole barn. Perfect for hobbyists, contractors, car enthusiasts, or RV owners, this structure includes: separate underground electric service, fully insulated interior, epoxy-coated concrete floors, two mini splits to condition the space, four overhead garage doors with remotes for easy access and a dedicated office space. You are sure to be impressed, Additional exterior features add even more value, including an RV dump station with water supply, rear chain link fencing, and a storage shed that conveys with a riding lawn mower. Enjoy peaceful mornings and quiet evenings surrounded by serene landscapes, open skies, and the tranquility of country living. This property combines charm, functionality, and privacy-a rare find in a truly serene location. Close to the ammenities of Shepherdstown, you will find downtown Shepherdstown feels like stepping into a well-kept 18th-century village. Most of the buildings are historic, and everything is close together, so you can park once and explore on foot. Expect unique storefronts and lots of preserved architecture. You can wander without a plan and enjoy all the town has to offer. Most cafés, shops, and restaurants are within a 5-minute stroll of each other. The town feels peaceful and lived-in - not touristy or commercial.P op into a local book store with character, find handmade crafts and local art, antiques and vintage treasures, outdoor and bike shops, cozy gift shops and specialty stores. Its the kind of town where you walk into a store and end up chatting with the owner. If this sounds like something you are looking for, schedule your showing today and make this your home.

Holiday Price Reduction!!! This charming split-level home rests on nearly half of an acre at the end of a cul-de-sac within five minutes of downtown, historic Shepherdstown! Hardwood flooring runs throughout the living areas on the main floor including the living, dining and kitchen spaces while large windows throughout provide an abundance of natural light. The main living area transitions to the hallway with three bedrooms along with one full and one half bathrooms. An additional full bathroom is located on the lower level!!! This lower space also provides additional finished living room; currently used as a second primary sleeping area. The multiple windows provide natural light while the full glass door leads to a level walk out side entry. A long paved driveway provides plenty of off street parking. Enjoy restful evenings grilling on the long rear deck or relaxing in the partially fenced-in backyard. Recent upgrades include a NEW ROOF in 2024, along with new refrigerator, microwave, and water heater in 2025!! Don't miss this adorable home, tucked away at the end of the cul-de-sac and ready for a new owner!

Welcome to 136 Woodcock Ave - a spacious 3-bedroom, 1.5-bath rancher set on nearly half an acre in the established Mecklenburg Heights community. Offering comfortable one-level living and a wide, gently wooded lot, this home blends everyday ease with the quiet charm of a well-loved neighborhood just minutes from historic Shepherdstown. Step inside to a bright living room that sets a warm, welcoming tone and leads naturally into the updated kitchen. Modern finishes, ample counter space, and an efficient layout make cooking and daily routines feel effortless. Low-maintenance flooring extends throughout, and the adjoining mud/laundry room adds convenience right off the kitchen. * Professional Photos will be added shortly * The bedroom wing features 3 comfortable rooms with easy access to a full bath plus an additional half bath, creating a practical layout that works well for residents and guests. Soft natural light brightens each space, giving the home a relaxed and inviting feel throughout. Out back, a large deck overlooks the tree-lined edge of the property - perfect for morning coffee, evening dinners outdoors, or quiet moments at home. Recent improvements including newer siding, windows, roof, and HVAC offer added peace of mind and long-term value. Residents of Mecklenburg Heights enjoy the benefits of an established community with modest HOA dues and well-maintained surroundings. The location places you just minutes from Shepherdstowns locally loved cafés, boutiques, and seasonal events, as well as Shepherd University and scenic walking paths along the Potomac River. Commuters will appreciate easy access to Martinsburg, Harpers Ferry, Route 45, and major travel corridors throughout the Eastern Panhandle. With thoughtful updates, effortless one-level living, and a setting that blends convenience with small-town charm, this property is an exceptional opportunity in a sought-after Shepherdstown community.

1585 Gardners Lane: Circa 1850 Farmhouse converted into 6 apartments, 2 cottages and 1 duplex totaling 10 units on 13.2 acres with huge bank barn and fencing/pasture for horses. 100% occupancy, great rental history over past 20 years of ownership. Roughly $11k per month totaling a potential yearly income of $132,910 (2025). Current owner operated and managed these units as short term rentals on month to month leases. Some tenants have remained for many years. One tenant leases a cottage and all the fenced areas and barn for an equestrian business. Tenants pay electric, owner provides Wi-Fi and trash removal. All tenants are on month to month leases. Multiple wells and septic systems. NOTE: 48 HOURS REQUIRED FOR ALL SHOWINGS.

Welcome to 414 McMurran Farm Lane, this remarkable property was built for comfort, leisure, and everyday ease. Offering over 5,600 square feet of beautifully designed living space and an adjoining lot (Lot 6) for a total of 18+ acres, this property delivers a rare combination of luxury, functionality, and rural tranquility. From the moment you arrive, the mature tree lined driveway and expansive 365 degree views create a serene and inviting atmosphere. Inside, the home features new wide plank hardwood floors, new crown molding and wainscoting, and custom built-in carpentry throughout, including desks, bookcases, mudroom lockers, and more. The main level includes a generous primary suite and a thoughtful floor plan enhanced by new granite countertops, several new appliances, exceptional storage, and a convenient dog/utility shower in the mudroom. Two gas fireplaces add warmth and charm, while the fully finished walkout basement provides additional space for comfort, by including its own kitchen & full bathroom making it the perfect space for guests, extended family. Outdoor living is a standout with a heated pool, pergola, granite outdoor bar, hardscape patio, and a built-in fire pit, creating a true retreat for relaxation or hosting gatherings. And if you want to enjoy the best of both indoor and outdoors just relax in the sunroom which is temperature controlled and inviting all year round. You and your guest will always have ample parking for your gatherings with the extended driveway and oversized two car garage. So whether you are lounging poolside or relaxing on the front porch watching the sun go down this home has something for everyone to enjoy. For horse lovers, hobby farmers, and anyone seeking a self-sustaining lifestyle, the property includes an impressive equestrian setup and agricultural features. The barn offers two horse stalls and a dedicated tack area, while the fenced paddocks and lighted riding arena provide an excellent environment for training, exercising, and everyday care. Two run-in sheds offer additional shelter, and the high tunnel is ideal for gardening or year-round growing. The acreage and community allow for horses, goats, chickens, and other small livestock, giving you the freedom to maintain the farm or homestead of your dreams. Plus the finished detached garage functions beautifully as a workshop, home gym, or car enthusiast space. Additional highlights include well-maintained HVAC and home systems, abundant closets and storage throughout, new granite counters, and a built-in security and fire alarm system (subscription required for monitoring). If you commute daily then you will really enjoy that its located within minutes to a MARC station in a peaceful neighborhood with large rural lots, this exceptional estate offers privacy, versatility, and endless possibilities while remaining close to everyday conveniences. 414 McMurran Farm Lane is more than a home, it's a lifestyle waiting to be experienced.

Welcome to 286 Starkeys Landing, a spacious 3-bedroom, 2.5-bath townhome quietly set within the established Starkeys Landing community of Shepherdstown, West Virginia. Offering just over 2,100 square feet of finished living space, this home blends warmth, comfort, and light in a way that feels immediately like home. The lower level opens through a bright two-story foyer where sunlight filters through tall transom windows and warm oak railings rise toward the main living space above. This entry level includes a flexible finished area with wide-plank floors, a charming barn-style door, and large daylight windows-an inviting setting for a recreation room, home gym, or quiet office retreat. A laundry area and ample storage complete this thoughtfully designed level. Upstairs, the main level unfolds in an open, effortless flow designed for everyday living. Handsome wood-look floors run throughout, leading from the spacious family room-anchored by large windows and an airy ceiling fan-to the adjoining dining area and kitchen beyond. The kitchen offers abundant oak cabinetry, dark granite countertops, and stainless-steel appliances, with generous workspace for cooking or gathering. A cheerful breakfast nook framed by triple windows opens to the deck, extending the living space outdoors for easy entertaining or peaceful evenings under the stars. The upper level is filled with natural light and calm energy. The primary suite serves as a private retreat, featuring a sitting area framed by bright windows, dual closets, and a well-appointed bath with dual vanities, a soaking tub, and a separate shower. Two additional bedrooms, both with ceiling fans and double closets, share a full hall bath with neutral finishes and warm tile floors. Set within a peaceful Shepherdstown enclave, this home enjoys close proximity to Morgans Grove Park, Shepherd University, and the historic charm of downtowns cafés and shops. Commuters will appreciate easy access to Route 340 and the nearby MARC Train station for travel into Maryland, Northern Virginia, and D.C. Blending modern comfort with small-town character, 286 Starkeys Landing captures the essence of Shepherdstown living-a light-filled home in a community that feels both connected and quietly removed, where every space invites you to slow down and simply feel at home.

**** Update***** This home comes with unique financing opportunities! The seller is willing to offer partial owner financing, creating additional flexibility for well-qualified buyers. Plus, our preferred lender offers special financing solutions designed to help buyers explore more accessible loan programs. Ask for details Lindal Cedar Home on 10.08 Acres of Peace & Beauty Tucked away on over ten acres of rolling woodland, 105 Rabbits Rest Lane is where timeless architecture meets tranquil living. This striking Lindal Cedar Home captures the essence of peace, privacy, and craftsmanship, created for those who value beauty in both structure and setting. Experience serenity and sophistication just minutes from Historic Shepherdstown, Harpers Ferry, Charles Town, and the Potomac River. This beautifully crafted residence showcases modern timber-frame architecture with a panoramic prow front, walls of glass, and vaulted ceilings that flood the great room with natural light while framing mountain and woodland views. Constructed with premium kiln-dried Western red cedar, the home combines classic elegance with comfortable livability. Inside, pine ceilings, white oak flooring, recessed lighting, and Corian countertops create a warm and inviting atmosphere throughout. The property features a private well and septic system, a 500-gallon buried propane tank that conveys, and a 2015 heat pump upgrade for year-round efficiency. Offering both privacy and convenience, the home is within easy reach of MARC train stations in Duffields, Harpers Ferry, and Brunswick,making commutes to the DC and Baltimore areas effortless. The land is graced by mature hardwoods, spring blooming dogwoods, and abundant wildlife, creating a peaceful, park-like setting that feels like a personal retreat. Covenants allow for domestic animals and select livestock such as horses, cattle, camelids, and poultry with proper containment, while swine are not permitted. With subdivision potential for two five-acre parcels, this property presents a rare opportunity to own a private sanctuary surrounded by nature yet close to everything Shepherdstown has to offer. 105 Rabbits Rest Lane is more than a home, its a retreat for the soul, offering space, beauty, and enduring peace in one of West Virginias most sought-after locations.

PRICE IMPROVEMENT...A MID WINTER OPPORTUNITY! In Cress Creeks coveted golf community, opportunities like this almost never appear. Only three double villas were ever built here - and the last one sold nearly a decade ago. Now, one of these rare homes is finally available, perfectly positioned on a beautiful .344â??acre lot with sweeping golf course views. Inside, sunlight fills the cathedralâ??ceiling great room, creating an airy, open feel from the moment you walk in. The main level is designed for easy living with a comfortable primary suite, a flexible second bedroom or office, and a kitchen that flows effortlessly into the living and dining spaces. Step out to the screened porch or rear deck and take in the peaceful course views - your own private backdrop for morning coffee or evening unwinding. Upstairs, a spacious loft adds a third bedroom, a full bath, and a huge storage room, while the sideâ??load garage and mainâ??level laundry keep life simple. Dualâ??zone heating and cooling ensure yearâ??round comfort. This is more than a villa - its a rare chance to live the Cress Creek lifestyle, where golf, dining, and the charm of historic Shepherdstown are just minutes away.

Experience the charm of this immaculately preserved 1912 stone house, set on over 2 acres in close proximity to historic Shepherdstown. This spacious 4-bedroom, 2-bathroom home features tall ceilings, hardwood floors, and a wide center hall on the main level. You'll also find two large bedrooms, a study, a cozy living room, a full bath, and a convenient laundry area. At the back of the home, the eat-in kitchen boasts a covered porch, perfect for grilling or outdoor dining. Upstairs, two additional large bedrooms await, along with a newly renovated full bath and an open attic space that offers potential for expansion. The exquisite details of this home, including wide window sills, transoms, intricate fireplace surrounds, and custom built-ins, reflect craftsmanship rarely seen in modern construction. Outside, two garage-style outbuildings and a circular drive create an estate-like atmosphere as you approach the front entrance. With numerous possibilities for residential or potential commercial use, this property is currently operated as a successful Airbnb and is move-in ready, impeccably clean, and maintained by the same family for over 60 years!

This all-brick colonial is a true classic. It sits of over 3 and 1/2 acres of Jefferson County's finest land. Your large lot is surrounded with trees for tons of privacy. Once you clear the trees on your long driveway you will be taken away by this home's curb appeal. A beautiful concrete path leads you from the driveway, passed the manicured landscaping, to the lovely front porch. Can't you just see yourself enjoying a cup of coffee or a glass of wine and taking in the beautiful views? Inside the front door you are greeted by a grand two-story foyer with hardwood floors and handsome transoms. To your left you have the formal living room with carpet, a ceiling fan, and tons of natural light. This space could also serve as a great office. Glass paned lead out to the kitchen. To the right of the foyer, you have the formal dining room. Here you'll find hardwood floors, built in bookshelves, and a gar fireplace. A butler's door to the pantry and kitchen make hosting dinner parties a breeze. The pantry is huge with wood shelving and provides plenty of space for your storage needs. Beyond this you have the open kitchen. It features a large two-tier island for extra storage and breakfast bar seating. This space is topped off by stainless appliances, recessed lighting, and crown molding. There is a large breakfast nook with hardwood floors and access to the rear deck. A decorative light fixture defines the space. Down the hall you have a large laundry room with easy-care vinyl floors and storage shelves. The main level full bath features vinyl floors, pedestal sink, and walk-in shower, so convenient for guests. The kitchen and breakfast nook are open to your spacious family room. This space features carpet, crown molding, and a gas fireplace. This set up is great for entertaining all year round. The large windows bathe you in natural light. Up the stairs you have a hall with hardwood floors. Bedroom 2 features carpet and is a junior suite with a private ensuite full bath. The ensuite features an extended single bowl vanity for ample storage and an acrylic tub/shower. Bedroom 3 features carpet ceiling fan and ample closet storage. Bedroom 4 features hardwood floors and chair railing molding. Bedrooms 3 & 4 share a large Jack and Jill bath. The bath features separate, extended single bowl vanities, and a water closet with toilet and tub/shower. The primary suite is carpeted and features vaulted ceilings and ceiling fan. Your suite includes a private ensuite bathroom with double bowl vanity, large soaking tub a walk-in shower. The suite is topped off by a huge walk-in closet with wood shelving. You will want for nothing in this private oasis. The 3 car garage keeps you, your car, and your yard tools/toys of out the weather. What a blessing in this heat! Outside you have a large rear deck that is perfect for hosting your summer BBQ's. A ramp provides access to the driveway and your rear yard. Rear yard has been cleared and is nice and level with mature trees all around. There is no shortage of privacy no matter where you are on your lot.

***PRICED BELOW CURRENT APPRAISAL*** The George Washington Hollida House 4781 Scrabble Rd, Shepherdstown, WV 25443â?¨5 Beds 2.5 Baths 2,721 Sq Ft 5 Unrestricted Acres Step into a piece of West Virginia history with the George Washington Hollida House, a stunning c.1840 brick Colonial I-House nestled on 5 UNRESTRICTED acres in scenic Scrabble, just minutes from historic Shepherdstown and the Potomac River. Rich in character and brimming with income potential, this distinctive property blends period charm with modern versatility. The main residence offers 2,721 square feet of finished living space, including five spacious bedrooms, two full bathrooms, and one half bath. Four bedrooms are located on the upper level with a full bath, while the fifth bedroom (or optional den) and another full bath are conveniently located on the main level. The home has five wood-burning fireplaces and one propane, wide-plank hardwood floors, classic plaster walls, and charming period details like mantelpieces and built-ins. The kitchen has been thoughtfully renovated with upgraded countertops, custom-painted cabinets, and modern appliances, offering a seamless blend of historic appeal and everyday functionality. A formal dining room, living room, and foyer provide multiple gathering spaces, mini split systems, and propane heating ensure year-round comfort. Step outside to enjoy a large front porch, brick courtyard, extensive hardscaping, and peaceful views of the partly wooded and landscaped lot. A metal roof, and solid brick construction speak to the durability and craftsmanship of this historic home. Adding to the propertys appeal is a charming guest cottage, currently operated as a highly-rated Airbnb, complete with a loft bedroom, studio space, full bath, and sauna-perfect for visiting family, a private artists retreat, or a standalone rental. A black walnut bank barn, built in 1945, features a 16x32 workshop and abundant storage. The property previously operated as a highly-rated Airbnb, making it an incredible opportunity for investors or anyone looking to live where they earn. The unrestricted acreage create potential for tiny homes, RV pads, or event spaces. Located in Berkeley County (not within city limits), this one-of-a-kind estate offers easy access to Martinsburg, Shepherdstown, and Potomac River Dam 4-ideal for kayaking, fishing, or simply enjoying the outdoors.

Come tour this fantastic move-in ready home located in Shepherdstown, WV. Boasting 4 bedrooms and 4.5 baths, this property sits on a corner lot with a partially fenced backyard and a new Trex deck. Numerous upgrades include a new upstairs A/C unit, fresh paint throughout all three floors, new basement carpeting, new washer and dryer, and professional landscaping. The main level features hardwood floors and a dual staircase. A private office is located to the right upon entry, and to the left a spacious den opens into the dining room. The kitchen showcases dark-stained cabinetry, light granite countertops, and stainless steel appliances, including a double oven. The kitchen flows into an open dining area and two-story living room with a stone fireplace and vaulted ceiling. A rear door leads to the Trex deck-ideal for relaxing or entertaining. Upstairs offers four bedrooms and a laundry room with extra cabinets. The primary suite includes French doors, a massive walk-in closet, and a private bath with dual vanities, soaking tub, and walk-in shower. Bedroom two has its own attached bath, while bedrooms three and four share a Jack and Jill bath. The finished basement includes a large recreation room with backyard walkout, a full bath, and two unfinished rooms for storage or a home gym. Located in The Point subdivision just three miles from downtown Shepherdstown, this home is convenient to The Club at Cress Creek, Martinsburg, Charles Town, and Harpers Ferry-Best part it's only 80 miles from Washington, D.C. and Baltimore.