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SHEPHERDSTOWN

One of the most popular communities provided by Charis Realty Group

SHEPHERDSTOWN

About SHEPHERDSTOWN

Discover Shepherdstown,WV Real Estate 

Welcome to Shepherdstown, WV — One of West Virginia’s Most Charming and Historic Communities!

Nestled along the picturesque banks of the Potomac River, Shepherdstown is renowned for its quaint small-town ambiance, rich history, and vibrant cultural scene. If you’re searching for exceptional real estate opportunities in a friendly, walkable neighborhood, look no further than Shepherdstown, WV.

Why Choose Shepherdstown, WV for Your Next Home?

Shepherdstown is not just a place to live—it’s a lifestyle. This historic town blends beautiful architecture, lush natural scenery, and modern amenities, making it perfect for families, retirees, and anyone seeking a close-knit community.

Top Features of Shepherdstown Real Estate

  • Historic homes with unique character and timeless appeal
  • Modern developments and single-family houses
  • Spacious lots with mature trees and river views
  • Quiet, safe streets ideal for walking and biking

Benefits of Living in Shepherdstown

1. Rich History & Culture

Shepherdstown is the oldest town in West Virginia, offering a unique blend of colonial charm and contemporary arts. Enjoy local galleries, live theater at the Contemporary American Theater Festival, and fascinating museums.

2. Top-Rated Schools

Families appreciate the highly rated local schools, as well as educational opportunities at Shepherd University, located right in the heart of town.

3. Outdoor Recreation

Whether you love hiking the C&O Canal, kayaking on the Potomac, or biking the scenic country roads, there’s always an outdoor adventure waiting.

4. Vibrant Downtown

Stroll through Shepherdstown’s quaint downtown, featuring:

  • Unique boutiques
  • Independent bookstores
  • Farm-to-table restaurants and cozy cafes

5. Community Spirit

Get involved in local events, farmer’s markets, art walks, and annual festivals, where neighbors become friends and memories are made.

Explore Available Properties

Shepherdstown, WV real estate offers diversity for every taste and budget, including:

  • Charming historic homes
  • New construction single-family houses
  • Waterfront properties
  • Townhomes and condos
  • Acreage for custom builds

Explore the latest Shepherdstown, WV real estate listings here.

Invest in Shepherdstown, WV Real Estate Today

Shepherdstown offers a superb quality of life, outstanding investment potential, and timeless beauty—making it one of the best places to buy a home in West Virginia.

Ready to find your dream home in Shepherdstown? Contact a local expert on the Charis Realty Group team for personalized guidan ce and the latest market insights!

Experience the charm, history, and community spirit of Shepherdstown, WV—your perfect new neighborhood awaits.

One of the most popular communities provided by Charis Realty Group
31
# of Listings
4
Avg # of Bedrooms
$394
Avg. $ / Sq.Ft.
$580,028
Med. List Price

Browse SHEPHERDSTOWN Real Estate Listings

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

31 Properties Found. Page 1 of 3.

**** 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.
#WVJF2020174

SHEPHERDSTOWN

105 RABBITS REST LANE

3 Beds

2 Baths

2,500 Sq.Ft.

$975,000

MLS#: WVJF2020174

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.
#WVJF2020612

SHEPHERDSTOWN

1585 GARDNERS LANE

6 Beds

6 Baths

3,692 Sq.Ft.

$1,600,000

MLS#: WVJF2020612

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.
#WVJF2020542

SHEPHERDSTOWN

1585 GARDNERS LANE

10 Beds

None Baths

3,692 Sq.Ft.

$1,600,000

MLS#: WVJF2020542

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 it’s 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.
#WVJF2020498

SHEPHERDSTOWN

414 MCMURRAN FARM LANE

5 Beds

4 Baths

5,641 Sq.Ft.

$1,599,999

MLS#: WVJF2020498

Beautiful 20.62± acres featuring a large metal barn, an already-dug well (see septic and well records), and a fully fenced property currently used for cattle. Property includes a nice gravel driveway, a cleared house site, and a perfect blend of lovely, wooded areas and open pasture for animals. Located less than 10 minutes from downtown Shepherdstown, this property offers the ideal balance of privacy and convenience. Come enjoy nature, peace, and wide-open space just minutes from Shepherdstown. Two lots being sold together: 14.76 AC LOT 1 & MERGER P/O PCL 12.1 EATON SD (14.76 AC, Managed Timber) is located in Berkeley County, and LT 2 NEEDY FARM (5.86 AC) is located in Jefferson County. Buyer shall perform their own due diligence regarding all county-specific requirements, property characteristics, and intended uses. There is an existing grave site on the property. Buyer is responsible for conducting all investigations related to this gravel site and any associated permissions, restrictions, or operations. Seller makes no representations or warranties and shall not be held responsible for any findings related to the gravel site or buyer’s intended use of the property.
#WVJF2020628

SHEPHERDSTOWN

160 OTTER RUN PLACE

None Beds

None Baths

20.62 acres

$1,100,000

MLS#: WVJF2020628

PRIME LAND adjacent to Shepherd University, Domino's, and, across the street from WVU Medical PRIME LAND adjacent to Shepherd University, Domino's, and, across the street from WVU Medical Facility and ROC's convenience store! SENECA CROSSING NORTHSIDE apartment concept... 40 units have been approved for this site...five buildings of eight units each. Perfect site for much needed apartments. House on the property is unlivable and there is approval to teardown. Approved trail connectivity out back corner of lot to Shepherd University's Wellness Center. Engineering completed by Mills Group. All plans available for review. Vesting good for approximately 34 additional months before construction must begin. DOH entrance permit in hand and bonded with $25000. Capacity letter in hand for Shepherdstown water and sewer. DHHR permit in hand. NOTICE: ALL Approvals may need updated or renewed.
#WVJF2010760

SHEPHERDSTOWN

8285 MARTINSBURG PIKE

None Beds

None Baths

3.7 acres

$825,000

MLS#: WVJF2010760

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.
#WVJF2021778

SHEPHERDSTOWN

48 FIELD CREST COURT

5 Beds

4 Baths

4,583 Sq.Ft.

$715,000

MLS#: WVJF2021778

***PRICED BELOW CURRENT APPRAISAL*** The George Washington Hollida House | 4781 Scrabble Rd, Shepherdstown, WV 25443
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 property’s 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 artist’s 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.
#WVBE2038756

SHEPHERDSTOWN

4781 SCRABBLE ROAD

5 Beds

2 Baths

2,721 Sq.Ft.

$695,000

MLS#: WVBE2038756

Nestled just minutes from the heart of historic Shepherdstown, this home offers the charm of small town living with unbeatable convenience. Known for its vibrant arts scene, cozy cafes, local boutiques and one of the oldest universities in the country, Shepherdstown has a warmth and culture all its own. Home to Shepherd University; a vibrant campus with many events including theatre shows, art festivals and the Wellness Center providing plenty of indoor events and is literally just down the road a few miles. Outdoor recreation like hiking and kayaking on the Potomac river provide nature's enjoyment. This home's premier location is in the Cress Creek golf course neighborhood of Fernbank and just minutes from Cress Creek Golf Club, the C & O towpath, the Bavarian Inn and a vibrant downtown, rich with historic architecture and youthful energy. This home boasts a private 3 season addition to relax on as well as a low maintenance deck featuring a Sun setter electric shade Recently refreshed with paint throughout as well as new carpeting upstairs, this home is ready for your next lifestyle adventure. Features include built in speakers for the custom sound set up in the living room, library and bonus room, hardwood floors, custom made shelves and cabinets in the library , a utility room with sink and a walk in pantry. A whole house Generac generator comes on without fuss if the power goes out. Close to 480 for direct access to the MARC commuter rail station in Harpers Ferry which goes to Washington DC Union Station. Membership packages in "The Club" vary - see the Cress Creek website for more information about the golf course, swimming pool and tennis courts (or pickleball).
#WVJF2022094

SHEPHERDSTOWN

63 HACKBERRY CIRCLE

3 Beds

2 Baths

2,345 Sq.Ft.

$649,900

MLS#: WVJF2022094

Major price improvement! 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!
#WVJF2020060

SHEPHERDSTOWN

104 E GERMAN STREET

None Beds

None Baths

4,416 Sq.Ft.

$599,900

MLS#: WVJF2020060

LAST RIVER FRONT lot available at Shepherds Cove 5.4 Acre beautiful wooded lot sited on a bluff overlooking the Potomac River. BEAUTIFUL UNOBSTRUCTED VIEWS UP AND DOWN THE RIVER. Located in the shadow of historic Shepherdstown ,Shepherds Cove is a unique community for those selective home buyers who prefer woods and natural topography as their view , and golf carts as their preferred means to go to their boat, the putting green, the pavilion overlooking the Potomac, or just visiting a neighbor. It's a resort-like community for a small group of selective owners. A setting of unspoiled natural dramatic beauty. .Offering extensive hiking and biking paths and private access to twelve navigable miles of the beautiful Potomac River . Enjoy fishing, boating, swimming in a peaceful secure setting. Away from it all yet convenient location. Minutes to downtown Shepherdstown, Shepherd University , boutique shops, Great restaurants. An area of interesting folks, and cultural activities. Daily MARC Commuter Train to DC, 50 miles to Washington DC and Baltimore. Exceptional opportunity. Motivated seller. CALL FOR A TOUR
#WVBE2032288

SHEPHERDSTOWN

Lot 9 SHEPHERDS COVE SWIFT RIVER WAY

None Beds

None Baths

5.3 acres

$562,000

MLS#: WVBE2032288

Welcome to 185 Shepherd Lane, a charming and spacious home just minutes from downtown Shepherdstown, WV. Situated on 2.5076 acres in a peaceful, established neighborhood with large lots, this 4-bedroom, 2.5-bath home offers both comfort and opportunity. A covered front porch welcomes you into the main level, which features a formal living room and dining room (both with beautiful hardwood floors) perfect for hosting, and a cozy family room with a wood-burning fireplace (currently capped) and built-in shelving. There's also a private office or bonus room with natural light and a generously sized mud/laundry room for daily convenience. Upstairs, you'll find all four bedrooms, including a primary suite with its own ensuite bath, while the three additional bedrooms share a full hall bath. The kitchen remains in its original condition—clean and well-kept—providing a great opportunity to update and make it your own. The unfinished basement offers plenty of storage or future expansion possibilities. Recent updates include a new roof in 2025 and a modern HVAC system installed within the past few years. Outside, the in-ground pool is currently not operational, but it remains in place for buyers who wish to restore or reimagine the space. This home offers a rare combination of space, charm, and location—ready for your next chapter in beautiful Shepherdstown.
#WVJF2021232

SHEPHERDSTOWN

185 SHEPHERD LANE

4 Beds

2 Baths

2,176 Sq.Ft.

$550,000

MLS#: WVJF2021232

Platted as Seneca Crossing. DRIVE THROUGH WINDOWS ALLOWED! Bring on the fast food, coffee shop, bakery, etc. This parcel was part of a 4.44 parcel that was sold to WVU Medical Center which is adjacent. ROCS's convenience store is also adjacent. Dominos' is across the road. A 40 unit apartment complex has been approved for across the road as well! This pad will be available for mixed use. Also, another pad (Lot 3) would be available at additional cost. If you need to combine two lots, Jefferson County Planning Co. would have to approve. Water and sewer available. Shepherd University and the corporation pedestrian friendly!
#WVJF2018260

SHEPHERDSTOWN

Lot 2 MARTINSBURG PIKE

None Beds

None Baths

0.67 acres

$500,000

MLS#: WVJF2018260

Drive through windows allowed! Bring on the fast food, coffee or bakery! This Lot 3 parcel, was part of a 4.44 acre piece that WV Medical purchased part of and built the medical center adjacent. Lot 2, is also available at an additional cost. ROC's convenience store is adjacent as well! Combining the lots would need Jefferson County Planning Co. approval. Water and sewer available. Property appraised. Shepherd University and the town within pedestrian distance! 40 unit apartment building has been approved by the county across the road! Lots of exciting things happening in our town! Bring your ideas!
#WVJF2018258

SHEPHERDSTOWN

Lot 3 MARTINSBURG PIKE

None Beds

None Baths

0.79 acres

$500,000

MLS#: WVJF2018258

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!
#WVJF2021592

SHEPHERDSTOWN

126 RIDERWOOD WAY

5 Beds

3 Baths

2,914 Sq.Ft.

$499,990

MLS#: WVJF2021592

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