Property located in one of the nicest subdivisions in Jefferson County. Home over 5,600 finished square feet, kitchen with updated stainless appliances, breakfast area adjacent to living room. Beautiful wood floors throughout most of the house. Basement has a bedroom and full bath, large rec room, gym area and plenty of storage. Amazing views from all windows, rear deck off the living room backs to orchard and walking trail. Extensive hardscape, stone retaining wall, and rear patio off basement bonus room. it just breath taking. Seller expended over 5K in blinds. A/C and Heat with dual type of fuel Roof around 3 years old Must see.
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!
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! 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!
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!
Welcome to historic Shepherdstown living! This adorable 3-bedroom, 1-bath home is perfectly situated just off Main Street in the heart of downtown. Surrounded by the charm and history of one of West Virginia's oldest towns, this property is also conveniently located near Shepherd University. The current owners have thoughtfully updated the home with a new HVAC system, roof, kitchen, bathroom, flooring, new deck and fresh interior paint. On-street parking adds to the ease of downtown living. A rare chance to enjoy modern comforts wrapped in historic small-town charm.
Shepherdstown on a Half Acre and NO HOA! Close to downtown Shepherdstown and Shepherd University for UNDER 300K!! This cozy home features 3 bedrooms, 2.5 baths, fireplace and fully fenced back and Side fenced area. Large separate dog kennel area that is perfect for dog owners! Is also a good college student rental option. New stainless-steel dishwasher, riding lawn mower and outside Shed included. Seller is motivated, just lowered price! Appraised for $310,000 recently.
PRIME LOCATION!! This 3 bedroom / 1.5 bathroom rancher has new paint and is ready for its new owners! Conveniently located in the popular Shepherdstown zip code, this property provides a private country setting, but has easy access to all of the modern amenities and historic attractions visitors travel from all across the country to experience! Don't miss this unique opportunity! Schedule your appointment TODAY!
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 property’s 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. It’s 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.
Historic Downtown Charm Meets Modern Comfort Welcome to 103 E New St — a distinctive historic home in the heart of Shepherdstown, West Virginia, just steps from cafes, shops, Shepherd University, and the C&O Canal National Historical Park. This thoughtfully updated 3-bedroom, 2.5-bath residence blends the warmth of original character with modern conveniences. Step inside to find rich original hardwood floors, tall windows, built-in shelving, and a cozy pellet stove anchoring the living space. The kitchen offers charming custom wood cabinetry, butcher-block counters, and stainless-steel appliances, while the formal dining room showcases period built-ins and timeless trim details. The second level includes 2 additional bedrooms and a primary suite with private balcony, ideal for morning coffee or sunset views. The updated primary full bath features a walk in closet and a large glass-enclosed shower, air jet spa tub, and tile accents — a relaxing retreat. Additional features include in-home laundry, efficient systems, and a standing-seam metal roof. Enjoy the fenced backyard with off-street parking with gardens full of perennials and just a short stroll from everything Shepherdstown offers. Perfect as a primary residence, investment property, or weekend retreat, this home captures the charm of small-town living with convenient access to commuter routes to DC/NOVA.
Welcome to 207 W High Street located in beautiful and historic Shepherdstown, West Virginia. With Shepherdstown being established in 1762 and one of the oldest towns in West Virginia, this 1790 built home plays a strong role in the community and holds historical significance. The Shepherdstown Historic District was established and added to the National Register of Historic Places in 1973, with a boundary expansion to include the entire town in 1987. One block from Shepherd University and one block from German Street, walkable to the shopping, restaurants, bars, entertainment, arts, and culture, this is the perfect location for both functionality and entertainment. A highlight of this property is it sits on a lot that borders the Shepherd University football field. The lot is adorned with garden areas, mature trees, a wide range of foliage, bamboo grove, flagstone walk/steps, and a large barn storage/shed. Upper and lower decks present, so whether you're hosting friends or enjoying a quiet evening, the outdoor space is designed to be loved by all. The tall bamboo allows you to enjoy the lower back deck and outdoor shower area with privacy. Upon entering the home, you are greeted with timeless charm. The updated kitchen features granite counter tops, state of the art counter-top gas range, stainless steel refrigerator, attractive birch cabinetry, ceramic earth toned tiles, opening to the dining area and French doors to the back upper deck. The rest of the main level has stunning hardwood floors, a library/ study with built-in floor-to-ceiling bookshelves, and tall windows giving plenty of natural light. The living room contains a woodstove on its custom brick hearth in front of the high brick wall and mantel. Upstairs, you’ll love the three light-filled bedrooms, wood floors and full bath with pedestal sink. The larger main bedroom has a separate attached dressing room. The sizable basement, with concrete floors, interior stairs and exit to lower-level deck, houses the laundry room, storage shelving and shop areas. This property is an undeniably amazing location and is full of potential. Call today for more information and schedule a showing.
Quick Move In! Located in Tollhouse Woods, Shepherdstown's newest community located just a mile from the downtown area and University. This property backs to a tree line and sits on a private homesite. 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!
New Reduced Price! Welcome home to this charming rancher nestled on 1.8 acres in beautiful Shepherdstown. Enjoy the ease of one-level living with the added potential of a full, walk-out basement—perfect for future expansion or storage. Inside, you’ll find all NEW gorgeous LVP flooring, new carpets in bedrooms, Upgraded kitchen & new appliances, a cozy fireplace area and a spacious primary suite with a large bathroom. The breezeway off the kitchen leads to a convenient two-car garage, combining charm and functionality in one package. This home offers comfort, character, and plenty of room to make it your own!
Welcome home to this beautiful colonial right in the heart of Shepherdstown, but just outside of city limits. This home features the perfect blend of historic charm and modern living , where every detail invites you to call it home. This charming, well maintained 1920 Colonial-style home boasts two bedrooms, two full baths and over 1,500 sq. ft. of living space! Featuring stunning wood floors that exude warmth and character. The thoughtfully designed interior includes a combination kitchen/dining area, perfect for entertaining. The kitchen is equipped with energy-efficient appliances, including a refrigerator, oven/range, and dishwasher. Right off of the kitchen is a cozy study with exposed brick, and leads you into the perfect sized living room. Also on the main level, you will find a full bathroom and laundry room. Upstairs you will find an expansive primary bedroom, with a private deck, and loft. The additional space of the loft is perfect for a reading nook, study, or office space. Indulge in comfort and relaxation with a luxurious soaking tub in the primary ensuite! The additional bedroom upstairs is also of amble size. In the fenced in backyard you will find two more outdoor living spaces, AND a sizeable shed that has electric and can be imagined into any additional space your family wants! With off-street parking and a spacious driveway, convenience of strolling to downtown Shepherdstown and Shepherd University at your doorstep- what more could you want! Enjoy fine dining, shopping, college football games, nail salons, weekly farmer's market- with out ever starting your car! The current homeowners used this property as a very profitable AirBnB, imagine a home that not only offers aesthetic charm but also promises strong returns in a desirable location. This home is perfect for everyone!
**** 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, it’s a retreat for the soul, offering space, beauty, and enduring peace in one of West Virginia’s most sought-after locations.
PRICE IMPROVEMENT...A MID WINTER OPPORTUNITY! In Cress Creek’s 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 .344-acre lot with sweeping golf course views. Inside, sunlight fills the cathedral-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 side-load garage and main-level laundry keep life simple. Dual-zone heating and cooling ensure year-round comfort. This is more than a villa — it’s a rare chance to live the Cress Creek lifestyle, where golf, dining, and the charm of historic Shepherdstown are just minutes away.
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 Shepherdstown’s 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.
Beautifully Renovated Retreat on 3 Acres in Oakleigh Acres – A Rare Shepherdstown Find with four bedrooms and 3 bathrooms! Welcome to your dream home—a fully renovated, move-in-ready gem tucked away on three-level acres in the highly sought-after Oakleigh Acres community of Shepherdstown, WV. Offered with a ONE-YEAR HOME WARRANTY. This property delivers the perfect fusion of sleek modern style and serene country living, just minutes from golf courses, Shepherd University, coffee shops, and the scenic Potomac River. Step Inside & Be Wowed! The main level showcases a designer kitchen featuring a bold waterfall granite island, stainless steel appliances, newly installed hardwood floors, a new tiled backsplash, abundant cabinetry, and a recently professionally painted interior. Updated lighting fixtures added. Newly updated stylish lighting fixture just added! A brand-new picture window frames a sun-soaked living room with wall molding in the dining and living areas. The open dining area flows seamlessly to a brand-new deck—ideal for hosting or relaxing under the stars. Comfort Meets Style Upstairs: Three spacious bedrooms and three luxurious, fully updated bathrooms provide comfort and elegance, all finished with today’s most stylish touches. Lower Level Bonus Living: Enjoy a massive great room with a cozy brick accent wall, a dedicated office or study nook, and convenient walk-out access to the backyard. A large laundry room adds exceptional storage and utility space. Dream Bonus Building: Don’t miss the oversized two-story detached building with new electric, perfect for a workshop, studio, possible garage apartment, loft, or ultimate storage solution. Let your imagination run wild! Get the best of both worlds! Enjoy peaceful rural views, daily visits from deer, wild turkeys, and the birds from the adjoining bird sanctuary. Enjoy the freedom of open space—all just minutes from downtown Shepherdstown. Whether you're looking for a retreat, a family home, or a unique work-from-home haven, this one checks every box. Homes like this rarely come available—especially with land, luxury, and location. Put this one on your list today! The inspection has been done, and the home is close to perfection!
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 Morgan’s Grove Park, Shepherd University, and the historic charm of downtown’s 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.
What a home and property! Nearly one-and-a-half park-like acres in Shepherdstown set the stage for this stately colonial-style home. A fenced rear yard is great for two-legged and four-legged friends and a mixture of mature trees and open spaces in all directions provides a magical and private sensation. Despite this far, far away feeling, modern conveniences are readily at hand. Comcast Xfinity IS available and Shepherdstown is only a very short drive away. Additionally, there are great neighbors in all directions. Though the home is beautiful everywhere, pay special attention to the light and airy kitchen, with a brand new dishwasher and countertops clad in exquisite quartz, as well as to the massive primary bedroom and bathroom that is a picture of luxury and modernity. A wood stove on the main level brings comfort on the especially chilly nights and the mostly-finished basement is a great place to gather, watch TV, play games, and for guests to call it a night. This home feeds the well-loved Shepherdstown Elementary and Shepherdstown Middle Schools and the NEW Shepherdstown Elementary is extremely close by. However, if the concern is for older students, rather than younger ones, then of course Shepherd University is only a short drive away as well. Commuting to Maryland/Northern Virginia is easy as well, as the home is only about 30 minutes from I-70 and less than an hour from Dulles. Additional peace-of-mind comes from a roof, gutters, and downspouts that were JUST replaced in August. Don't miss this special and unique property! IF YOU LIKE WHAT YOU SEE, CALL !!!!!
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!
Shepherdstown is located in West Virginia. Shepherdstown, West Virginia has a population of 1,529. Shepherdstown is more family-centric than the surrounding county with 45.87% of the households containing married families with children. The county average for households married with children is 33.51%.
The median household income in Shepherdstown, West Virginia is $53,125. The median household income for the surrounding county is $86,711 compared to the national median of $69,021. The median age of people living in Shepherdstown is 21.8 years.
The average high temperature in July is 86.3 degrees, with an average low temperature in January of 20.9 degrees. The average rainfall is approximately 40.7 inches per year, with 20 inches of snow per year.
