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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
40
# of Listings
3
Avg # of Bedrooms
$283
Avg. $ / Sq.Ft.
$477,081
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

18 Properties Found. Page 1 of 2.

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

New on site 1 day ago
A rare gem nestled on over two pristine acres in a coveted water-access community, this stunning brick rancher offers the perfect blend of elegance, comfort, and natural beauty. Boasting four generously sized bedrooms and two full baths on the main level, the home is thoughtfully designed for both everyday living and effortless entertaining. Step into the impressive living room, where a vaulted ceiling and a warm gas fireplace create an inviting, light-filled space, beautifully shared with the owner’s suite for a touch of everyday luxury. Unwind in the tranquil glass-enclosed sunroom, where panoramic, park-like views showcase mature landscaping and abundant wildlife, offering a peaceful retreat in every season. With direct access from both the owner’s suite and the dining room, this space seamlessly connects indoor comfort with outdoor charm. The partially finished basement expands the home’s versatility, featuring a full kitchen and full bath—ideal for guests, extended living, or entertaining. Enhanced by recent updates throughout, this exceptional property is truly move-in ready and poised to deliver the lifestyle you’ve been waiting for.
#WVBE2048594

SHEPHERDSTOWN

238 COMSTOCK DRIVE

4 Beds

3 Baths

3,192 Sq.Ft.

$499,900

MLS#: WVBE2048594

To Be Built — an exciting opportunity to create your dream home in a peaceful setting with a sought-after Shepherdstown address. This thoughtfully designed rancher will offer over 1,700 square feet of comfortable, single-level living, all situated on more than two unrestricted acres. The home will feature attractive board-and-batten siding, a stylish hip roof, and a welcoming front porch—perfect for enjoying the surrounding countryside. Set against a tranquil, farm-like backdrop, the property provides expansive front and backyard space, ideal for relaxing, entertaining, or simply taking in the open, serene landscape. Inside, you’ll find modern finishes including 9-foot ceilings, recessed lighting, and a well-planned layout designed for both everyday living and effortless entertaining. A cozy fireplace will serve as a focal point for the main living area, adding warmth and charm, while the spacious 3-car garage offers ample room for vehicles, storage, or hobbies. One of the best advantages of this home is the timing—there’s still an opportunity to secure it before completion and truly get in on the ground floor of something special. Please note: buyer to pay transfer tax stamps at closing. Don’t miss your chance to own a beautiful new home in a peaceful setting with room to grow. Reach out today for more details and to explore this incredible opportunity.
#WVBE2049868

SHEPHERDSTOWN

Lot B-13 FOREMAN ROAD

3 Beds

2 Baths

1,700 Sq.Ft.

$484,900

MLS#: WVBE2049868

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.

$479,990

MLS#: WVJF2021592

Quick Move In w/ walkout basement! Nearly a 1/4 acre homesite and mountain views. Complete with main level bedroom, and finished basement rec room! Only a stone's throw away from Morgan's Grove Park Entrance. This 2 Story single family home marries features and affordability and comes with everything included. 5 Bedrooms, LVP floors in the main living spaces, included kitchen appliances, granite countertops and Espresso cabinets give the updated look you've always wanted. Located next to Morgan's Grove Park and just down the street from Downtown Shepherdstown!
#WVJF2023208

SHEPHERDSTOWN

124 OPEN GATE LANE

5 Beds

3 Baths

2,914 Sq.Ft.

$469,990

MLS#: WVJF2023208

New on site today
None
#WVJF2022732

SHEPHERDSTOWN

6 RAMS COURT

5 Beds

2 Baths

2,911 Sq.Ft.

$465,000

MLS#: WVJF2022732

Don't miss out on this rare opportunity to own nearly 8 UNRESTRICTED acres in Shepherdstown. Sweeping sunset views make this a perfect location to lay down roots and build your forever home. Build with confidence as major groundwork is already complete. Perc-approved for a 4-bedroom house with well already in place. Experience true flexibility to build your dream home with NO HOA. Although the property itself does not have an HOA, it is situated off of a state maintained road making it accessible but private. Lot is conveniently located close to Route 9, ideal for commuters. If country living with access to modern conveniences is what you seek, then look no further than this picturesque property.
#WVJF2020954

SHEPHERDSTOWN

RIDGE ROAD

None Beds

None Baths

7.85 acres

$449,900

MLS#: WVJF2020954

Back on the market with a price improvement. Our loss is your gain! Welcome to this beautifully maintained all-brick rancher situated on a picturesque one-acre lot surrounded by pastoral and mountain views. Offering two bedrooms and one full bath, this home provides comfortable single-level living in a peaceful rural setting while still being conveniently located. Step outside and discover the property’s standout feature—an impressive, recently built 30' x 48' x 16' top-of-the-line pole barn. Perfect for hobbyists, contractors, car enthusiasts, or RV owners, this structure includes: separate underground electric service, fully insulated interior, epoxy-coated concrete floors, two mini splits to condition the space, four overhead garage doors with remotes for easy access and a dedicated office space. You are sure to be impressed, Additional exterior features add even more value, including an RV dump station with water supply, rear chain link fencing, and a storage shed that conveys with a riding lawn mower. Enjoy peaceful mornings and quiet evenings surrounded by serene landscapes, open skies, and the tranquility of country living. This property combines charm, functionality, and privacy—a rare find in a truly serene location. Close to the ammenities of Shepherdstown, you will find downtown Shepherdstown feels like stepping into a well-kept 18th-century village. Most of the buildings are historic, and everything is close together, so you can park once and explore on foot. Expect unique storefronts and lots of preserved architecture. You can wander without a plan and enjoy all the town has to offer. Most cafés, shops, and restaurants are within a 5-minute stroll of each other. The town feels peaceful and lived-in — not touristy or commercial.P op into a local book store with character, find handmade crafts and local art, antiques and vintage treasures, outdoor and bike shops, cozy gift shops and specialty stores. It’s the kind of town where you walk into a store and end up chatting with the owner. If this sounds like something you are looking for, schedule your showing today and make this your home.
#WVJF2020848

SHEPHERDSTOWN

4381 ENGLE MOLERS ROAD

2 Beds

1 Baths

864 Sq.Ft.

$445,000

MLS#: WVJF2020848

Welcome to 183 Riderwood Way—situated on nearly a 1/3 acre homesite, this spacious two-story home blends comfort, style, and affordability. Featuring 4 bedrooms, a second-floor loft, and durable LVP flooring throughout the main living areas, there’s room for everyone to live and grow. The kitchen comes fully equipped with included appliances, granite countertops, and white cabinetry, delivering the modern look you’ve been searching for. A finished rec room in the basement provides valuable additional living space—perfect for a media room, play area, or home gym. Located next to Morgan’s Grove Park and just down the street from Downtown Shepherdstown, you’ll enjoy both convenience and charm. Why wait to build when you can move now? This less-than-a-year-old home is in pristine condition and shows like a model. Perfect for outdoor enthusiasts, with nearby hiking trails and close proximity to the Potomac River for endless adventure. It’s also an excellent location for commuters—offering easy access to surrounding areas—while still allowing you to return home to the peaceful feel of a small-town community.
#WVJF2022778

SHEPHERDSTOWN

183 RIDERWOOD WAY

1 Beds

5 Baths

2,969 Sq.Ft.

$435,000

MLS#: WVJF2022778

Quick Move In! Back to Trees private quarter acre homesite! Located in Tollhouse Woods, Shepherdstown's newest community located just a mile from the downtown area and university. This property backs to a tree line and sits on a private homesite. This 2 Story single family home marries features and affordability and comes with everything included. 4 Bedrooms, LVP floors in the main living spaces, included kitchen appliances, granite countertops and white cabinets give the updated look you've always wanted. Located next to Morgan's Grove Park and just down the street from Downtown Shepherdstown!
#WVJF2023210

SHEPHERDSTOWN

42 RIDERWOOD WAY

4 Beds

3 Baths

2,401 Sq.Ft.

$429,990

MLS#: WVJF2023210

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

2,048 Sq.Ft.

$425,000

MLS#: WVJF2020494

Discover the charm of this beautifully maintained colonial townhouse nestled in the desirable Maddex Farm community, an ideal location, offering quiet streets and convenient access to all of the area's amenities. Wonderfully updated with LVP flooring throughout the main floor, an appealing kitchen design that is just as functional, and a fully finished walkout basement that adds lifestyle flexibility, this townhouse is a move-in ready gem. With three well-sized bedrooms, three full bathrooms, and a fully finished basement with space for a 4th bedroom, office, or secondary living area, there is plenty of space for relaxation and privacy. Outside are a peaceful deck and patio that both back to trees for quiet enjoyment. Freshly cleaned and painted, and located in a vibrant neighborhood offering easy access to local amenities, University and wellness center, and convenient shopping, it's a perfect place to call home. Experience the perfect blend of comfort, style, and community in this exceptional townhouse. Don’t miss your chance to make it yours!
#WVJF2022920

SHEPHERDSTOWN

43 RYAN COURT

3 Beds

3 Baths

1,835 Sq.Ft.

$329,900

MLS#: WVJF2022920

None
#WVJF2021398

SHEPHERDSTOWN

19 CARDINAL DRIVE

3 Beds

1 Baths

1,352 Sq.Ft.

$309,000

MLS#: WVJF2021398

1 2
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Calculating Capital Gains
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