CHARIS REALTY GROUP
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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 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 Group
43
# of Listings
4
Avg # of Bedrooms
$321
Avg. $ / Sq.Ft.
$609,301
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

43 Properties Found. Page 2 of 3.

Terrific floor plan for the buyers that need a bedroom on the first floor! Lots of nice landscaping surrounds the house. Architectural shingled roof is only two years old. Inside, the two story foyer beckons you to an open, bright (also two story) great room accented by a beautiful Palladian window. Wood burning gas fireplace (gas pipe there for an easy conversion) and the balcony overlook highlight the room! An easy flow to the large eat in gourmet kitchen and formal dining room on one side and then the master suite is off to the right on the other. Large master bath was just redone a few years ago. A living room (or future office) is also off the foyer entrance. The great room opens to the deck and the kitchen opens to a beautiful screened porch. Laundry is on the first floor off the kitchen and garage. A surprise back stairway off the kitchen leads to a really nice finished bonus room (which could be a 4th bedroom) upstairs plus two more bedrooms and a bath! Another stairway is off the foyer, making this a fun adventure for children and grandchildren. to run and hide in circles! This home offers lots of light and has many updates besides the roof, from a new furnace to some new floors. Located in the beautiful golf course community of Cress Creek. See "The Club" at Cress Creek, Shepherdstown online! All different kinds of memberships available from a full membership to just swimming, golf, or tennis. Located on 5 minutes out of Shepherdstown and Shepherd University as well as commuter routes.
#WVJF2016544

SHEPHERDSTOWN

44 N TAMARAC DRIVE

3 Beds

2 Baths

2,975 Sq.Ft.

$625,000

MLS#: WVJF2016544

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. Offered with a ONE-YEAR HOME WARRANTY. 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, a new tiled backsplash, abundant cabinetry, and a recently professionally painted interior. 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, wild turkeys, and the birds from the adjoining bird sanctuary. Enjoy 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 is close to perfection!
#WVJF2020062

SHEPHERDSTOWN

79 CHANDLER DRIVE

4 Beds

3 Baths

2,460 Sq.Ft.

$569,900

MLS#: WVJF2020062

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

In Cress Creek’s coveted golf community, opportunities like this almost never appear. Only three double villas were ever built here — and the last one sold nearly a decade ago. Now, one of these rare homes is finally available, perfectly positioned on a beautiful .344‑acre lot with sweeping golf course views. Inside, sunlight fills the cathedral‑ceiling great room, creating an airy, open feel from the moment you walk in. The main level is designed for easy living with a comfortable primary suite, a flexible second bedroom or office, and a kitchen that flows effortlessly into the living and dining spaces. Step out to the screened porch or rear deck and take in the peaceful course views — your own private backdrop for morning coffee or evening unwinding. Upstairs, a spacious loft adds a third bedroom, a full bath, and a huge storage room, while the side‑load garage and main‑level laundry keep life simple. Dual‑zone heating and cooling ensure year‑round comfort. This is more than a villa — it’s a rare chance to live the Cress Creek lifestyle, where golf, dining, and the charm of historic Shepherdstown are just minutes away.
#WVJF2020058

SHEPHERDSTOWN

200 MEADOW RIDGE DRIVE

3 Beds

3 Baths

2,446 Sq.Ft.

$549,000

MLS#: WVJF2020058

New Reduced Price! 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.

$510,000

MLS#: WVJF2020426

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

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

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 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.

$482,500

MLS#: WVJF2020848

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

2,914 Sq.Ft.

$469,990

MLS#: WVJF2018712

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.

$460,000

MLS#: WVJF2020494

Immediate Move In! Backs to Trees! Walk out Basement w/ finished Rec Room! Located in Downtown Shepherdstown! This property and sits on a flat and spacious homesite, one of the largest in the community! 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!
#WVJF2021040

SHEPHERDSTOWN

144 RIDERWOOD WAY

4 Beds

2 Baths

2,969 Sq.Ft.

$449,990

MLS#: WVJF2021040

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

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

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