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$649,900
4 Beds ⋅ 3 Baths
**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

Listing courtesy of ERA Liberty Realty. Contact: (304) 728-2000
$285,000
3 Beds ⋅ 1 Baths
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

Listing courtesy of Path Realty. Contact: 3042796950
$560,000
4 Beds ⋅ 3 Baths
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

Listing courtesy of Exit Success Realty. Contact: 3043501281
$400,000
3 Beds ⋅ 3 Baths
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

Listing courtesy of Real Estate Teams, LLC. Contact: 3016953020
$1,799,900
An exceptional opportunity to own one of historic Shepherdstown’s most iconic mixed-use commercial properties in the heart of West Virginia’s oldest town! Prominently situated on a .173-acre commercially zoned corner parcel along East German Street, this landmark building, originally constructed in 1906, offers an impressive 9,000 + total square feet of versatile space, blending timeless architectural character with outstanding investment potential. Spanning approximately 9,000 square feet, the property presents a versatile layout well-suited for a variety of commercial, hospitality, retail, office, or mixed-use opportunities. The main level features expansive restaurant and pub space with large storefront windows, prominent street frontage, inviting dining areas, bar service, and a commercial infrastructure established presence along one of the town’s most traveled corridors create exceptional exposure for any business venture. An upper-level leased commercial business unit offers the added benefit of supplemental rental income, also creating an attractive investment opportunity. Steeped in history and prominently positioned within Shepherdstown’s vibrant downtown business district, the property also enjoys exceptional visibility and year-round pedestrian traffic from residents, visitors, tourists, and the Shepherd University community. Surrounded by locally owned boutiques, acclaimed restaurants, galleries, entertainment venues, historical landmarks, and just moments from the Potomac River, this location places your investment at the center of one of the region’s most charming and thriving destinations. Whether preserving its legacy as a celebrated dining and gathering place, transforming it into a boutique hospitality destination, or capitalizing on its mixed-use potential, the possibilities are remarkable. Properties of this size, prominence, and historic significance rarely become available in downtown Shepherdstown!

201 E German St, Shepherdstown

Listing courtesy of Path Realty. Contact: 3042796950
$800,000
3.85 acres. General Commercial. The Gateway to Shepherdstown! Position your next investment just minutes from downtown Shepherdstown and Shepherd University. This location benefits from a steady flow of local residents, university traffic, commuters, and tourists drawn to the area's historic charm, shopping, dining, and cultural attractions. Rarely does a parcel of this size, visibility, and strategic location become available in the Shepherdstown market. The building is in need of substantial renovation and is being offered as-is, with the property's greatest value in its outstanding commercial location and redevelopment potential.

7174 Martinsburg Pike, Shepherdstown

Listing courtesy of Mclntosh Realty Group. Contact: (304) 582-1852
$749,000
3 Beds ⋅ 3 Baths
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

Listing courtesy of Burch Real Estate Group, LLC. Contact: (681) 252-3002
$597,000
4 Beds ⋅ 4 Baths
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

Listing courtesy of Samson Properties. Contact: 3049305621
$325,000
3 Beds ⋅ 4 Baths
Welcome to 45 Ryan Court, where low-maintenance living meets the charm and character of historic Shepherdstown. Nestled in the desirable Maddex Farm community, this spacious three-level townhome offers approximately 1,900 square feet of comfortable living space with 3 bedrooms, 2 full baths, and 2 half baths. The inviting main level features a bright, open floor plan that seamlessly connects the living and dining areas, creating an ideal space for everyday living and entertaining. The kitchen offers ample cabinetry and workspace with easy access to outdoor living. Upstairs, the spacious primary suite provides a private retreat complete with an en-suite bath, while two additional bedrooms offer flexibility for family, guests, or a home office. The finished lower level expands your living space and is perfect for a recreation room, media room, fitness area, or work-from-home setup, complete with an additional half bath. Enjoy the convenience of living just minutes from downtown Shepherdstown, where you'll find locally owned restaurants, coffee shops, boutiques, and year-round community events. Outdoor enthusiasts will appreciate nearby walking trails, parks, the Potomac River, and easy access to the C&O Canal Towpath. Commuters will enjoy convenient access to Charles Town, Martinsburg, Harpers Ferry, and Maryland and Northern Virginia. Whether you're looking for your first home, a weekend getaway, or an investment opportunity, this move-in-ready townhome offers the perfect combination of comfort, convenience, and the unique lifestyle that makes Shepherdstown one of West Virginia's most sought-after communities.

45 Ryan Ct, Shepherdstown

Listing courtesy of Samson Properties. Contact: 3049305621
$722,400
Discover a remarkable 17.2-acre lot, perfectly poised for investment or your dream retreat. This parcel offers a level terrain, ensuring ease of development while providing a serene escape from the hustle and bustle. Nestled on a no-thru street, it guarantees privacy and tranquility, making it an ideal canvas for your vision. Imagine waking up to breathtaking views of lush pastures and towering trees, creating a picturesque backdrop for your future home or investment property. The absence of nearby developments enhances the sense of seclusion, while still being conveniently accessible. This lot presents a unique opportunity for investors seeking to capitalize on the growing demand for spacious, nature-rich properties. With its expansive size and desirable features, the potential for appreciation is significant. Embrace the chance to create a legacy in this idyllic setting, where comfort meets opportunity. Don't miss out on this exceptional investment!

Otter Run Pl Unit #LOT 3, Shepherdstown

Listing courtesy of Samson Properties. Contact: 3049305621
$800,000
3.85 acres. General Commercial. The Gateway to Shepherdstown! Position your next investment just minutes from downtown Shepherdstown and Shepherd University. This location benefits from a steady flow of local residents, university traffic, commuters, and tourists drawn to the area's historic charm, shopping, dining, and cultural attractions. Rarely does a parcel of this size, visibility, and strategic location become available in the Shepherdstown market.

7174 Martinsburg Pike, Shepherdstown

Listing courtesy of Mclntosh Realty Group. Contact: (304) 582-1852
$329,000
3 Beds ⋅ 4 Baths
Welcome to this Sun-Drenched and Spacious Townhome with Brick Façade, Serene Wooded Views, 3 Bedrooms, 2 Full Bathrooms, and 2 Half Baths. Recent updates include Refinished Hardwood Floors, Newly Installed Redefined Pine Floors, recent New Deck Floor Boards, and an almost new HVAC System that was installed in 2024. Comcast cable and Xfinity are available. Enjoy the perfect blend of town and country! SELLER OFFERS BUYER A $5,000 CREDIT AT CLOSING. This home is conveniently located near the new Shepherdstown Library, Morgan’s Grove Park, and the unique restaurants and shops of historic downtown Shepherdstown. Your options for adventure are nearly endless, with the Potomac River, C&O Canal, Harpers Ferry, Charles Town, Martinsburg, the Appalachian Trail, and lots of Outdoor Recreation with MARC commuter and Amtrak passenger train stations in the area. Visit https://shepherdstown.info/ for more information, to request the email newsletter, and to view the calendar of local events.

39 Swearingen Way, Shepherdstown

Listing courtesy of Snyder Bailey & Associates. Contact:

$3,500,000
Rare commercial opportunity in Shepherdstown offering exceptional visibility, flexibility, and investment potential. Ideally situated directly off Route 45 at a signalized intersection and just minutes from Historic Shepherdstown, this prime corner property benefits from dual access from Martinsburg Pike and Old Martinsburg Road, ensuring convenient ingress and egress. The property features more than 15,000 square feet of commercial space, including a large open-concept area, office space, and two sets of bathrooms. The layout offers potential for multiple tenants with both lower and upper-level spaces, creating an excellent opportunity for owner occupancy or income-producing investment. A substantial parking area accommodates 100+ vehicles, providing ample parking for employees, clients, and visitors. This high-visibility location with strong traffic counts makes it ideal for medical, professional, educational, institutional, or office use. Tenants are responsible for any improvements necessary to customize the space to their business needs. The owner is open to a five-year lease agreement, providing long-term stability for prospective occupants. Located near vibrant downtown Shepherdstown, home to Shepherd University, the area offers an array of restaurants, boutiques, and cultural attractions. Convenient commuter access includes the Shepherdstown MARC train station and proximity to major transportation routes. The property is approximately 50 miles from the Washington, DC Beltway and offers convenient access to Eastern WV Regional Airport, Washington County Regional Airport, Dulles International Airport, Ronald Reagan Washington National Airport, and Baltimore/Washington International Airport.

7595 Martinsburg Pike, Shepherdstown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (304) 263-7800
$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
$171,950
3 Beds ⋅ 1 Baths
3 Bedroom 1 Bath home conveniently located in Shepherdstown. Convenient to shops, restaurants, college, and recreational C&O Canal & River. Buyers should exercise due diligence to verify all information & property details.

7341 Martinsburg Pike, Shepherdstown

Listing courtesy of Prime Location Realty, LLC. Contact: (304) 262-0800
$575,000
4 Beds ⋅ 4 Baths
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

Listing courtesy of Freedom Real Estate Group, LLC.. Contact: (304) 279-4162
$635,000
4 Beds ⋅ 3 Baths
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

Listing courtesy of Dandridge Realty Group, LLC. Contact: 3048857645
$439,000
3 Beds ⋅ 2 Baths
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

Listing courtesy of Samson Properties. Contact: 3049305621
$344,999
4 Beds ⋅ 3 Baths
New Price Improvement! The premier, three-level, corner lot townhome located in the Colonial Hills neighborhood of historic Shepherdstown, WV! Welcome to this beautifully renovated, move-in ready townhome, ideally located across from Morgan’s Grove Park and just minutes from downtown Shepherdstown’s shops, dining, and cultural charm. Offering almost 2,900 finished square feet across three thoughtfully designed levels, this 4-bedroom, 2.5-bath home blends modern luxury with timeless appeal. From the moment you arrive, the home impresses with its freshly painted exterior, professional landscaping, and carefully cleared surroundings for enhanced beauty and safety. Step inside to discover a fully finished lower level, a rare feature in the area, offering the ideal space for a telecommuting professional that is complete with a private home office, studio, and green screen. The heart of the home lies on the main living level, where a gourmet kitchen takes center stage with upgraded cabinetry, brand-new appliances, custom backsplash, and elegant lighting. Enjoy meals in the eat-in kitchen or the adjoining morning room, which flows effortlessly into a spacious living room with an electric fireplace that is perfect for cozy evenings or stylish entertaining. Throughout the home, no detail has been overlooked: Real wood floors on the second level and in the upstairs foyer, engineered wood flooring on the first floor (foyer, hallway, office), new wood steps throughout, marble flooring in the upstairs bathrooms and laundry room, new washer and dryer, first-floor toilet, and updated bath fixtures, crown molding and custom paintwork on the second level, modern circuit breaker and rebuilt heat pump with upgraded components, all-new recessed dimmable lighting, smoke detectors, and mounted TV with soundbar, and a brand-new Trex deck off the morning room, ideal for outdoor living. The third level hosts a serene primary suite retreat, featuring a walk-in closet, luxurious bath with sunken tub, separate shower, and double vanities. Two additional bedrooms share a full hall bath, offering comfortable accommodations for family or guests. With its generous space, elegant updates, and unbeatable location, this home offers a rare opportunity to enjoy the best of Shepherdstown living while being steps from nature, moments from town, and fully ready for modern life. Also, conveniently located to the nearby MARC Train, Shepherd University, C&O Canal, local shopping center, and so much more. Schedule your showing today and experience this exceptional home firsthand!

420 Starkeys Lndg, Shepherdstown

Listing courtesy of Path Realty. Contact: 3042796950
$515,000
4 Beds ⋅ 4 Baths
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

Listing courtesy of Greentree Associates of Shepherdstown, Inc.. Contact: 304-876-3737
$420,000
3 Beds ⋅ 3 Baths
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

Listing courtesy of Coldwell Banker Premier. Contact:

$374,900
3 Beds ⋅ 3 Baths
Discover the charm of this beautifully renovated Cape Cod home nestled in the desirable Maddex Farm community. With a major renovation completed in 2026, this residence boasts an excellent condition and upgrades throughout. The upgraded countertops and luxury vinyl plank flooring add a touch of elegance, while the breakfast area invites casual dining. This home features three comfortable bedrooms, including a main level primary en-suite with a walk-in closet, ensuring ample storage. Outside, the lot is situated on a peaceful cul-de-sac, providing a safe environment for outdoor activities. Across the street is community common space with a wooded stream area and just across from the intersection of Oatfield and Hensell is the community playground and picnic area. The community offers fantastic amenities, including basketball courts, playgrounds, and a paved walking path to the Shepherd University grounds at the Wellness Center. Using this path, literally 200 yards from your home, you can access safe travel to Shepherd University, downtown Shepherdstown, and the C and O Canal, all within walking or biking distance. With an attached garage and paved driveway, parking is a breeze.

35 Oatfield Ct, Shepherdstown

Listing courtesy of Samson Properties. Contact: 3049305621
$535,000
3 Beds ⋅ 4 Baths
Overlooking Cress Creek Golf Club in Shepherdstown, this villa-style duplex offers a setting that feels peaceful, established, and easy to enjoy. Hardwood floors run throughout the main level, where the layout balances comfort and function with a formal dining room, an eat-in kitchen with table space, and a spacious living room centered around a wood burning fireplace with built-in shelving. A large bay window with window seat brings in natural light, and the covered porch extends the living space outdoors with a view of Cress Creek Golf Course, that adds something special to daily life. The upper level includes a primary suite with ensuite bath, a second bedroom, full hall bath, and stacked washer and dryer. On the walkout lower level, a private bedroom suite with full bath, walkthrough closet, and patio access creates flexible space for guests, hobbies, or extended stays. Complete with a 2-car attached garage, this 3 bedroom, 3.5 bath home combines a scenic golf course backdrop with a floor plan designed for comfort, privacy, and ease. All this with easy access to all the restaurants, culture, and community that Shepherdstown, WV has to offer, just an hour outside of Washington, DC.

20 Drennen Ct, Shepherdstown

Listing courtesy of Dandridge Realty Group, LLC. Contact: 3048857645
$579,900
5 Beds ⋅ 4 Baths
Price Improvement! Stunning 5-bedroom, 3.5-bath Colonial tucked away on a private half-acre lot backing to mature trees in the sought-after Willow Springs Acres community of Shepherdstown, WV. Offering spacious living across three finished levels, this home combines timeless style, functional design, and peaceful outdoor living. Step inside to a dramatic 2-story foyer flanked by a private home office and elegant formal living room that seamlessly flows into the formal dining room—perfect for entertaining. The spacious eat-in kitchen is the heart of the home and features granite countertops, new stainless-steel appliances, a center island with breakfast bar seating, pantry, and sunny dining area. The kitchen opens to the expansive family room highlighted by a cozy wood stove and direct access to the screened-in porch overlooking the tree-lined backyard. A convenient half bath and laundry room complete the main level. Upstairs, the spacious primary suite offers a large walk-in closet and private en suite bath featuring dual vanities, a soaking tub, and separate shower. The additional bedrooms are all nicely sized, with Bedrooms 3 and 4 connected by a Jack-and-Jill bathroom for added convenience and functionality. The mostly finished lower level provides exceptional flexibility with a large recreation room, 5th bedroom, full bath, and abundant storage space—ideal for guests, multi-generational living, hobbies, or a home gym. Additional highlights include a side-entry 2-car garage, oversized driveway with ample parking, open-concept layout, and a serene backyard setting with added privacy. Conveniently located near historic Shepherdstown, commuter routes, dining, shopping, and outdoor recreation.

49 Appomattox Ln, Shepherdstown

Listing courtesy of Dandridge Realty Group, LLC. Contact: 3048857645
$215,000
Nestled on an expansive 5.96-acre canvas, in the private, gated community Shepherds Cove, this exceptional land opportunity offers a rare blend of natural beauty and luxurious potential. Imagine crafting your dream home surrounded by the serene embrace of towering trees and lush woods, where every sunrise and sunset paints the sky in breathtaking hues. The phenomenal sellers have crafted a true masterpiece in a "modern colonial" with expansive windows throughout. They are graciously offering to convey the house plans they created in conjunction with a local drafting company at closing. The plan was brought to life for this specific lot in mind lending itself to take in the picturesque native spring wildflowers, stone outcroppings, and lush wooded backdrop (see listing photos for illustration of house rendering). Shepherds Cove boasts exclusive community access to the Potomac River, inviting you to indulge in a lifestyle defined by tranquility and adventure. Where you can enjoy leisurely afternoons kayaking, fishing, or simply soaking in the peaceful ambiance that a riverfront location can provide. The gentle sounds of flowing water and the rustle of leaves create a symphony of nature that enhances the sense of home and comfort. The expansive nearly 6 acre lot is amongst the largest in the 19-lot community and offers ample space for your vision, whether it be a luxurious estate, a charming cottage, or a modern masterpiece. The possibilities are endless, allowing you to design a residence that reflects your personal style while harmonizing with the natural surroundings. Outdoor living spaces include a community riverfront pavilion with a kitchen/BBQ space, long meandering community hiking trails, gazebo, fire pit, bocce court, and marina storage space that seamlessly blend with the landscape, where you can entertain guests or unwind in solitude, all while enjoying the stunning views of the woods & river that envelop you. The proximity to the Potomac River enhances the allure, providing a perfect backdrop for outdoor activities and a peaceful retreat from the hustle and bustle of everyday life. With nearly 12 miles of navigable waters just steps away at the community river access, you can explore the river's beauty at your leisure, creating cherished memories. The lush greenery and natural features of the land offer a sense of privacy and seclusion, making it an ideal sanctuary where every day feels like a getaway. This is more than just land; it's a canvas for your dreams, a place where you can cultivate a lifestyle that celebrates the beauty of nature and the comforts of home. Discover the potential that awaits you in this extraordinary property, where luxury meets the great outdoors all within 1.5 hours of DC, Baltimore, MD, and Northern Virginia and in close proximity to MARC commuter train locations. Outside of the community, a leisurely stroll on the 184.5 mile C & O Canal Towpath, membership options at Cress Creek Golf Club or dining & entertainment options downtown Shepherdstown are all waiting to be explored. Nearby Shepherd University offers a range of activities to the community including a Wellness Center, the Life Long Learning program, as well as athletic events, concerts, lectures and plays throughout the year. Living in Shepherdstown embraces a lifestyle filled with community and local charm which was emphasized by its recognition as a 2026 recipient of the USA TODAY Readers’ Choice Top 10 Award for Best Historic Small Towns. Reach out today to gain access to explore this wonderful land opportunity!

Swift River Way, Unit #LOT 6, Shepherdstown

Listing courtesy of Greentree Associates of Shepherdstown, Inc.. Contact: 304-876-3737
$179,900
Build your dream home on this one of kind opportunity. Property features 0.75 Acres with public water and sewer available. One of the last remaining lots located in the North Hills section of The Club at Cress Creek which is the Eastern Panhandles only Private Country Club that features Golf, Tennis, Swimming, and Dining.

Lot #14 (North Hills) Briar Mountain Drive, Shepherdstown

Listing courtesy of Path Realty. Contact: 3042796950
$579,900
Major price improvement! This property is listed as a commercial listing under MLS# WVJF2020060 and multi-family property under MLS# WVJF2023040. Prime investment opportunity in the heart of historic Shepherdstown! This mixed-use property offers over 4,000 square feet of space and features five fully-leased rental units, generating steady monthly and annual income. With a strong rental history and a diverse tenant mix, this property provides a solid, turn-key investment opportunity. Ideally located just steps from popular shops, restaurants, and the campus of Shepherd University, the property benefits from consistent foot traffic and a dynamic community atmosphere. The combination of residential and commercial spaces within the building ensures a balanced and reliable income stream. Tenants enjoy proximity to everything downtown has to offer, while investors benefit from a stable return and long-term growth potential. This is a rare chance to own a high-performing income-producing asset right in the heart of Shepherdstown’s downtown district. Whether you’re looking to expand your real estate portfolio or invest in a highly desirable location with proven returns, this property checks every box. Schedule your private tour today and experience the value and potential this unique opportunity has to offer!

104 E German St, Shepherdstown

Listing courtesy of Path Realty. Contact: 3042796950
$535,000
3 Beds ⋅ 3 Baths
MOTIVATED SELLER...REDUCED $15k....This delightful semi detached home offers a perfect blend of comfort and style with an association that covers lawn care, snow removal, and common area maintenance, you can spend more time enjoying your home and less time on upkeep. Built in 2008, the villa-style residence boasts 2 spacious bedrooms and the adjoining room can easily be converted to 3rd and 2.5 bathrooms. Step inside to discover an inviting open floor plan that seamlessly connects the main level kitchen and living areas, enhanced by beautiful wood floors and natural light streaming through skylights and sliding doors that lead to the outdoor patio. The eat-in kitchen is an entertainer's dream, featuring upgraded countertops, an island for casual dining, plus a large pantry. Enjoy cozy evenings by the fireplace in the living room, or unwind in the primary suite, complete with a walk-in closet and a spa-like bathroom featuring a soaking tub and separate walk-in shower. The home is set on a well-maintained lot situated on a peaceful cul-de-sac. The attached garage provides convenient parking, with additional driveway space for guests. This property is not just a house; it’s a place to create lasting memories. Don’t miss the opportunity to make it your own! ALSO LISTING AGENT LIVES IN THE NEIGHBORHOOD! REACH OUT FOR ANY QUESTIONS!

61 Hartzell Dr, Shepherdstown

Listing courtesy of Coldwell Banker Premier. Contact:

$300,000
This 2-unit duplex just outside Shepherdstown offers incredible flexibility and income potential. Whether you're an investor seeking a strong rental opportunity or an owner-occupant looking to offset your mortgage, this property checks all the boxes. Live in one unit and rent the other, or maximize income by leasing both. Ideal for those with students attending Shepherd University, this property provides a smart housing solution—live on-site while generating rental income from the second unit or additional bedrooms. Set on a large lot backing to trees, the outdoor space offers privacy and room to enjoy nature. Each unit features its own private driveway and parking area for added convenience. A storage building conveys, and the nicely landscaped yard enhances the property's overall appeal. Conveniently located with easy access to Route 45, this property combines peaceful surroundings with commuter-friendly accessibility.

202 Old Martinsburg Rd, Shepherdstown

Listing courtesy of Century 21 Modern Realty Results. Contact: 304-263-2346
$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: