CHARIS REALTY GROUP
One of the most popular communities provided by {{page_data.agentName}}

SHEPHERDSTOWN

One of the most popular communities provided by Charis Realty

SHEPHERDSTOWN

About SHEPHERDSTOWN

Shepherdstown, WV Real Estate: Discover Your Perfect Home

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 Shepherdstown real estate agent for personalized guidance 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
54
# of Listings
3
Avg # of Bedrooms
$296
Avg. $ / Sq.Ft.
$520,878
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

54 Properties Found. Page 2 of 4.

This all-brick colonial is a true classic. It sits of over 3 and 1/2 acres of Jefferson County's finest land. Your large lot is surrounded with trees for tons of privacy. Once you clear the trees on your long driveway you will be taken away by this home's curb appeal. A beautiful concrete path leads you from the driveway, passed the manicured landscaping, to the lovely front porch. Can't you just see yourself enjoying a cup of coffee or a glass of wine and taking in the beautiful views? Inside the front door you are greeted by a grand two-story foyer with hardwood floors and handsome transoms. To your left you have the formal living room with carpet, a ceiling fan, and tons of natural light. This space could also serve as a great office. Glass paned lead out to the kitchen. To the right of the foyer, you have the formal dining room. Here you'll find hardwood floors, built in bookshelves, and a gar fireplace. A butler's door to the pantry and kitchen make hosting dinner parties a breeze. The pantry is huge with wood shelving and provides plenty of space for your storage needs. Beyond this you have the open kitchen. It features a large two-tier island for extra storage and breakfast bar seating. This space is topped off by stainless appliances, recessed lighting, and crown molding. There is a large breakfast nook with hardwood floors and access to the rear deck. A decorative light fixture defines the space. Down the hall you have a large laundry room with easy-care vinyl floors and storage shelves. The main level full bath features vinyl floors, pedestal sink, and walk-in shower, so convenient for guests. The kitchen and breakfast nook are open to your spacious family room. This space features carpet, crown molding, and a gas fireplace. This set up is great for entertaining all year round. The large windows bathe you in natural light. Up the stairs you have a hall with hardwood floors. Bedroom 2 features carpet and is a junior suite with a private ensuite full bath. The ensuite features an extended single bowl vanity for ample storage and an acrylic tub/shower. Bedroom 3 features carpet ceiling fan and ample closet storage. Bedroom 4 features hardwood floors and chair railing molding. Bedrooms 3 & 4 share a large Jack and Jill bath. The bath features separate, extended single bowl vanities, and a water closet with toilet and tub/shower. The primary suite is carpeted and features vaulted ceilings and ceiling fan. Your suite includes a private ensuite bathroom with double bowl vanity, large soaking tub a walk-in shower. The suite is topped off by a huge walk-in closet with wood shelving. You will want for nothing in this private oasis. The 3 car garage keeps you, your car, and your yard tools/toys of out the weather. What a blessing in this heat! Outside you have a large rear deck that is perfect for hosting your summer BBQ's. A ramp provides access to the driveway and your rear yard. Rear yard has been cleared and is nice and level with mature trees all around. There is no shortage of privacy no matter where you are on your lot.
#WVJF2018212

SHEPHERDSTOWN

150 MORGANA DRIVE

4 Beds

4 Baths

3,060 Sq.Ft.

$649,900

MLS#: WVJF2018212

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 GERMAN STREET E

None Beds

None Baths

4,416 Sq.Ft.

$649,900

MLS#: WVJF2020060

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 !!!!!
#WVJF2019978

SHEPHERDSTOWN

55 HIDDEN VALLEY CIRCLE

4 Beds

3 Baths

4,278 Sq.Ft.

$599,900

MLS#: WVJF2019978

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!
#WVJF2019968

SHEPHERDSTOWN

7765 MARTINSBURG PIKE

4 Beds

2 Baths

3,582 Sq.Ft.

$574,900

MLS#: WVJF2019968

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. 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, new tiled backsplash, abundant cabinetry, and recently professionally painted. 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 and wild turkeys, and 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 perfected! The home has been meticulously cleaned, and the work is done!
#WVJF2020062

SHEPHERDSTOWN

79 CHANDLER DRIVE

4 Beds

3 Baths

2,460 Sq.Ft.

$569,900

MLS#: WVJF2020062

MOTIVATED SELLER LAST CHANCE Last river front lot available at Shepherds Cove. Beautiful wooded lot sited on a bluff overlooking the Potomac River. BEAUTIFUL UNOBSTRUCTED VIEWS UP AND DOWN THE RIVER. Exceptional opportunity.
#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.
#WVJF2019608

SHEPHERDSTOWN

185 SHEPHERD LANE

4 Beds

2 Baths

2,176 Sq.Ft.

$550,000

MLS#: WVJF2019608

Rare Villa Opportunity in Sought-After Cress Creek Golf Community A rare find in one of Shepherdstown’s most desirable neighborhoods—only three double villa units like these were ever built in Cress Creek, and the last one sold nine years ago! Perfectly sited on a beautiful .344-acre lot with golf course views, this home offers refined comfort and effortless living. Step inside to an open-concept layout featuring a cathedral-ceiling great room filled with natural light. The main-level primary en-suite provides easy one-level living, while a second main-level bedroom or flex space offers versatility for guests or a home office. The kitchen with peninsula opens seamlessly to the living and dining areas, ideal for both everyday living and entertaining. Enjoy the outdoors from the screened porch or rear deck, both overlooking the scenic course. Additional highlights include main-level laundry, a side-load two-car garage, and an upper-level loft with a third bedroom, third full bath, and huge storage room. Comfort is ensured year-round with a dual-zone heat pump system. Experience the Cress Creek lifestyle—where golf, dining, and the charm of historic Shepherdstown are just minutes from your door.
#WVJF2020058

SHEPHERDSTOWN

200 MEADOW RIDGE DRIVE

3 Beds

3 Baths

2,446 Sq.Ft.

$549,000

MLS#: WVJF2020058

New Listing in Shepherdstown, West Virginia! 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!
#WVJF2020426

SHEPHERDSTOWN

104 STONEHOUSE LANE

3 Beds

2 Baths

2,006 Sq.Ft.

$525,000

MLS#: WVJF2020426

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

Great Commercial lot right next to Morgan Grove Park containing almost 3 acres with Kearneysville Pike Road frontage. There are endless possibilities with this lot. Public water and sewer is right up the street. Come take a look.
#WVJF2010846

SHEPHERDSTOWN

KEARNEYSVILLE PIKE

None Beds

None Baths

N/A

$499,900

MLS#: WVJF2010846

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.
#WVJF2020494

SHEPHERDSTOWN

207 W HIGH STREET

4 Beds

2 Baths

2,748 Sq.Ft.

$499,000

MLS#: WVJF2020494

Quick Move In! Walkout Basement and Finished Rec Room! Sits on nearly a 1/4 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!
#WVJF2018712

SHEPHERDSTOWN

92 OPEN GATE LANE

5 Beds

3 Baths

3,129 Sq.Ft.

$495,990

MLS#: WVJF2018712

New on site 3 days ago
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 brick sidewalks, quirky 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.
#WVJF2020848

SHEPHERDSTOWN

4381 ENGLE MOLERS

2 Beds

1 Baths

1,064 Sq.Ft.

$487,500

MLS#: WVJF2020848

1 2 3 4

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here