CHARIS REALTY GROUP
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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

13 Properties Found. Page 1 of 1.

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

Quick Move In! Located in Tollhouse Woods, Shepherdstown's newest community located just a mile from the downtown area and University. This property backs to a tree line and sits on a private homesite. This 2 Story single family home marries features and affordability and comes with everything included. 4 Bedrooms, LVP floors in the main living spaces, included kitchen appliances, granite countertops and white cabinets give the updated look you've always wanted. Located next to Morgan's Grove Park and just down the street from Downtown Shepherdstown!
#WVJF2020720

SHEPHERDSTOWN

95 RIDERWOOD WAY

4 Beds

2 Baths

2,148 Sq.Ft.

$452,490

MLS#: WVJF2020720

Welcome home to this beautiful colonial right in the heart of Shepherdstown, but just outside of city limits. This home features the perfect blend of historic charm and modern living , where every detail invites you to call it home. This charming, well maintained 1920 Colonial-style home boasts two bedrooms, two full baths and over 1,500 sq. ft. of living space! Featuring stunning wood floors that exude warmth and character. The thoughtfully designed interior includes a combination kitchen/dining area, perfect for entertaining. The kitchen is equipped with energy-efficient appliances, including a refrigerator, oven/range, and dishwasher. Right off of the kitchen is a cozy study with exposed brick, and leads you into the perfect sized living room. Also on the main level, you will find a full bathroom and laundry room. Upstairs you will find an expansive primary bedroom, with a private deck, and loft. The additional space of the loft is perfect for a reading nook, study, or office space. Indulge in comfort and relaxation with a luxurious soaking tub in the primary ensuite! The additional bedroom upstairs is also of amble size. In the fenced in backyard you will find two more outdoor living spaces, AND a sizeable shed that has electric and can be imagined into any additional space your family wants! With off-street parking and a spacious driveway, convenience of strolling to downtown Shepherdstown and Shepherd University at your doorstep- what more could you want! Enjoy fine dining, shopping, college football games, nail salons, weekly farmer's market- with out ever starting your car! The current homeowners used this property as a very profitable AirBnB, imagine a home that not only offers aesthetic charm but also promises strong returns in a desirable location. This home is perfect for everyone!
#WVJF2020712

SHEPHERDSTOWN

8709 SHEPHERDSTOWN PIKE

2 Beds

2 Baths

1,530 Sq.Ft.

$450,000

MLS#: WVJF2020712

Quick Move In! Main Level Primary Bedroom! Large Lot! This inviting Neuville floor plan offers the perfect blend of style & functionality, all on a single level for your comfort & convenience. Relax & enjoy the charming front porch, accentuated with tasteful stone accents. This spacious home boasts 4 bedrooms & 2 full bathrooms, providing ample space for family living. The open floor is designed for effortless entertaining. A generously sized kitchen island with elegant granite countertops serves as the centerpiece for both culinary creativity & casual dining. LVP flooring in the main area and carpet in the bedrooms. An oversized 2-car garage includes automatic opener. Thoughtful planning includes rough-ins for future ceiling fans in the family room & bedrooms, allowing you to customize your comfort. This home is one-level living combining practicality with a touch of elegance. Don't miss out on the opportunity to make this beautiful house your new home.
#WVJF2020722

SHEPHERDSTOWN

121 RIDERWOOD LANE

4 Beds

2 Baths

1,698 Sq.Ft.

$433,490

MLS#: WVJF2020722

Elegant Three-Level Townhome in 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!
#WVJF2018752

SHEPHERDSTOWN

420 STARKEYS LANDING

4 Beds

2 Baths

2,880 Sq.Ft.

$375,000

MLS#: WVJF2018752

Holiday Price Reduction!!! This charming split-level home rests on nearly half of an acre at the end of a cul-de-sac within five minutes of downtown, historic Shepherdstown! Hardwood flooring runs throughout the living areas on the main floor including the living, dining and kitchen spaces while large windows throughout provide an abundance of natural light. The main living area transitions to the hallway with three bedrooms along with one full and one half bathrooms. An additional full bathroom is located on the lower level!!! This lower space also provides additional finished living room; currently used as a second primary sleeping area. The multiple windows provide natural light while the full glass door leads to a level walk out side entry. A long paved driveway provides plenty of off street parking. Enjoy restful evenings grilling on the long rear deck or relaxing in the partially fenced-in backyard. Recent upgrades include a NEW ROOF in 2024, along with new refrigerator, microwave, and water heater in 2025!! Don't miss this adorable home, tucked away at the end of the cul-de-sac and ready for a new owner!
#WVJF2020606

SHEPHERDSTOWN

99 EXETER COURT

3 Beds

2 Baths

1,169 Sq.Ft.

$339,900

MLS#: WVJF2020606

Welcome to 286 Starkeys Landing, a spacious 3-bedroom, 2.5-bath townhome quietly set within the established Starkeys Landing community of Shepherdstown, West Virginia. Offering just over 2,100 square feet of finished living space, this home blends warmth, comfort, and light in a way that feels immediately like home. The lower level opens through a bright two-story foyer where sunlight filters through tall transom windows and warm oak railings rise toward the main living space above. This entry level includes a flexible finished area with wide-plank floors, a charming barn-style door, and large daylight windows—an inviting setting for a recreation room, home gym, or quiet office retreat. A laundry area and ample storage complete this thoughtfully designed level. Upstairs, the main level unfolds in an open, effortless flow designed for everyday living. Handsome wood-look floors run throughout, leading from the spacious family room—anchored by large windows and an airy ceiling fan—to the adjoining dining area and kitchen beyond. The kitchen offers abundant oak cabinetry, dark granite countertops, and stainless-steel appliances, with generous workspace for cooking or gathering. A cheerful breakfast nook framed by triple windows opens to the deck, extending the living space outdoors for easy entertaining or peaceful evenings under the stars. The upper level is filled with natural light and calm energy. The primary suite serves as a private retreat, featuring a sitting area framed by bright windows, dual closets, and a well-appointed bath with dual vanities, a soaking tub, and a separate shower. Two additional bedrooms, both with ceiling fans and double closets, share a full hall bath with neutral finishes and warm tile floors. Set within a peaceful Shepherdstown enclave, this home enjoys close proximity to Morgan’s Grove Park, Shepherd University, and the historic charm of downtown’s cafés and shops. Commuters will appreciate easy access to Route 340 and the nearby MARC Train station for travel into Maryland, Northern Virginia, and D.C. Blending modern comfort with small-town character, 286 Starkeys Landing captures the essence of Shepherdstown living—a light-filled home in a community that feels both connected and quietly removed, where every space invites you to slow down and simply feel at home.
#WVJF2020240

SHEPHERDSTOWN

286 STARKEYS LANDING

3 Beds

2 Baths

2,680 Sq.Ft.

$339,000

MLS#: WVJF2020240

Interior town home, 3BR, 2 1/2 bath, with over 2,220 finished square feet in the highly desired community of Colonial Hills Subdivision. 3 levels: Main level with foyer, half bath, laundry, rec room with sliding glass door to rear yard, potential 4th bedroom and a 1 car garage. Second level consists of a large living room, eat-in kitchen and sunroom/breakfast room. Third level consists of the master suite with walk-in closet/bathroom with soaking tub/dual vanity/separate shower, hallway full bath and two additional bedrooms. Located just directly across from Morgan's Grove Park and close proximity to Historic Shepherdstown, Shepherd University, Potomac River, shopping at many local retail shops and restaurants. Prepped and ready for your immediate occupancy.
#WVJF2018280

SHEPHERDSTOWN

115 SWEARINGEN WAY

4 Beds

2 Baths

2,220 Sq.Ft.

$299,900

MLS#: WVJF2018280

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