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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
70
# of Listings
3
Avg # of Bedrooms
$229
Avg. $ / Sq.Ft.
$479,033
Med. List Price

Browse SHEPHERDSTOWN Real Estate Listings

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$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

70 Properties Found. Page 2 of 5.

Come tour this fantastic move-in ready home located in Shepherdstown, WV. Boasting 4 bedrooms and 4.5 baths, this property sits on a corner lot with a partially fenced backyard and a new Trex deck. Numerous upgrades include a new upstairs A/C unit, fresh paint throughout all three floors, new basement carpeting, new washer and dryer, and professional landscaping. The main level features hardwood floors and a dual staircase. A private office is located to the right upon entry, and to the left a spacious den opens into the dining room. The kitchen showcases dark-stained cabinetry, light granite countertops, and stainless steel appliances, including a double oven. The kitchen flows into an open dining area and two-story living room with a stone fireplace and vaulted ceiling. A rear door leads to the Trex deck—ideal for relaxing or entertaining. Upstairs offers four bedrooms and a laundry room with extra cabinets. The primary suite includes French doors, a massive walk-in closet, and a private bath with dual vanities, soaking tub, and walk-in shower. Bedroom two has its own attached bath, while bedrooms three and four share a Jack and Jill bath. The finished basement includes a large recreation room with backyard walkout, a full bath, and two unfinished rooms for storage or a home gym. Located in The Point subdivision just three miles from downtown Shepherdstown, this home is convenient to The Club at Cress Creek, Martinsburg, Charles Town, and Harpers Ferry—Best part it's only 80 miles from Washington, D.C. and Baltimore.
#WVJF2015562

SHEPHERDSTOWN

60 HORNER FARM LANE

4 Beds

4 Baths

5,497 Sq.Ft.

$710,000

MLS#: WVJF2015562

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.

$679,900

MLS#: WVJF2018212

Welcome to Fernbank at Cress Creek, a neighborhood just down the road from Cress Creek Golf Club, and the well known Bavarian Inn of historic Shepherdstown. Enjoy the Cress Creek community complete with plenty of amenities not just catering to the golfer, with a swimming pool, tennis/pickle ball courts, 18 hole golf course, clubhouse, restaurant/bar facilities and wedding venue. This home was lovingly custom built with extra touches such as a private sunroom and deck in the rear, a large bonus room above the garage, and is completely wired for sound throughout the home. There are custom built cabinets and shelving in the front room as well as a golf cart garage/extra storage in the garage. Visit the close by wonderful, historic town amenities with Shepherd University just down the road (enjoy theatre there), downtown restaurants, or kayaking on the Potomac River and return home a short distance to a peaceful and private home on a cul-de-sac. Enjoy large decorative windows on the each floor front, ample storage in the basement and the bonus room over the garage with wonderful shelving and storage baskets just off the primary bedroom. Added value with a whole house Generac generator with instant on if power goes out! 2-10 Home Warranty included. Floor plans in documents.
#WVJF2016738

SHEPHERDSTOWN

63 HACKBERRY CIRCLE

3 Beds

2 Baths

2,945 Sq.Ft.

$659,900

MLS#: WVJF2016738

Absolutely gorgeous 4-bedroom, 3-bathroom, home with approximately 2878 total finished square feet, sitting on 8 UNRESTRICTED, PRIVATE ACRES in Shepherdstown. This property is in a great location, only 2.5 miles from Shepherd University and about 5 minutes from downtown Shepherdstown. Updates include: a NEW ROOF, NEW HVAC, new hot water heater, new siding, fresh paint from top to bottom, new wide plank LVP flooring, 3 new bathrooms, new hardware and fixtures. The kitchen has been renovated with new cabinets, new quartz counter tops, and new stainless-steel appliances. The fully finished basement has a new full bathroom. The front porch wraps around the side of the house and features new maintenance free Trex decking boards. 3 outbuilding convey with this property! Don't miss out! Schedule a showing TODAY!
#WVJF2016728

SHEPHERDSTOWN

89 MORGAN GROVE ROAD

4 Beds

3 Baths

2,978 Sq.Ft.

$650,000

MLS#: WVJF2016728

Absolutely gorgeous 4-bedroom, 3-bathroom, home with approximately 2878 total finished square feet, sitting on 8 UNRESTRICTED, PRIVATE ACRES in Shepherdstown. This property is in a great location, only 2.5 miles from Shepherd University and about 5 minutes from downtown Shepherdstown. Updates include: a NEW ROOF, NEW HVAC, new hot water heater, new siding, fresh paint from top to bottom, new wide plank LVP flooring, 3 new bathrooms, new hardware and fixtures. The kitchen has been renovated with new cabinets, new quartz counter tops, and new stainless-steel appliances. The fully finished basement has a new full bathroom. The front porch wraps around the side of the house and features new maintenance free Trex decking boards. 3 outbuilding convey with this property! Don't miss out! Schedule a showing TODAY!
#WVJF2016752

SHEPHERDSTOWN

89 MORGAN GROVE ROAD

4 Beds

3 Baths

2,978 Sq.Ft.

$650,000

MLS#: WVJF2016752

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

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

**Price Reduced** From the moment you arrive the curb appeal makes an impression. In the beautiful neighborhood of Willow Springs Acres, this corner lot stretches across .93 acres, with fresh landscaping and raised decorative brick flower beds just waiting to showcase your favorite blooms. The fully fenced backyard is a private oasis where kids and pets can play freely, complete with a wooden play set and trampoline that convey with the home. A large deck overlooks the yard, making it the perfect place to host summer cookouts or unwind in the evenings. Fruit trees—apples, peaches, and pears—add both beauty and bounty, while the oversized shed keeps your lawn and garden tools neatly stored. With a spacious driveway, there’s plenty of room for family and guests to park with ease. Luxury Inside and Out: Step inside the Sequoia model home and feel the grandeur of 9-foot ceilings, sun-filled rooms, and an open floor plan that’s ideal for both everyday living and entertaining. The kitchen has been thoughtfully updated with quartz countertops, white subway tile backsplash, luxury vinyl plank flooring, and a double oven. Expansive counters and 42-inch cabinets provide both function and style, while the open layout ensures you’re always part of the conversation. The family room, anchored by a cozy gas fireplace, flows seamlessly into the light-filled sunroom overlooking the backyard—an inspiring spot for morning coffee or an afternoon read. Upstairs, the master suite is nothing short of a retreat. A double-sided fireplace warms both the master bedroom and private sitting area, creating a space as inviting as it is spacious. The walk-in closet is exceptionally large, offering amazing organization, and the newly renovated master bath feels like a spa, complete with a free-standing soaking tub and oversized shower. Space for Everyone: The finished basement expands your options even further. With a full bathroom, sink, and mini kitchen cabinetry, plus its own washer and dryer, this space is perfect for a guest suite, in-law quarters, or even a private apartment. Whether you need a home office, a media room, or a teen hangout, this level offers endless flexibility. Peace of Mind Upgrades: Practical upgrades give this home long-lasting value: a brand-new roof installed in 2025 (with transferable warranty), new ceiling fans throughout, and a tankless hot water heater that ensures your family will never run out of hot water, and new paint in multiple rooms. Perfectly Located: Beyond the property itself, the location is unmatched. In just minutes you can be in historic Shepherdstown, exploring the shops, restaurants, and cultural gems that make it so special. Outdoor enthusiasts will love the easy access to Harpers Ferry, the Potomac River, and scenic hiking trails. Commuters will appreciate the convenience of Route 9, I-81, and the MARC train, putting Loudoun County, Charles Town, and the entire tri-state region within easy reach. This home offers the rare combination of elegance, space, and location. From hosting large gatherings to enjoying quiet nights by the fire, from planting gardens in spring to harvesting fruit in the fall—this is a home designed for the life you’ve been dreaming of.
#WVJF2019346

SHEPHERDSTOWN

27 COSTEN CIRCLE

5 Beds

3 Baths

4,850 Sq.Ft.

$625,000

MLS#: WVJF2019346

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 home has been meticulously cleaned, and the work is done!
#WVJF2020062

SHEPHERDSTOWN

79 CHANDLER DRIVE

4 Beds

3 Baths

2,460 Sq.Ft.

$589,900

MLS#: WVJF2020062

New on site 4 days ago
COMING SOON! Heads up on this over 4400 sq.ft. two story with a finished basement! Freshly painted throughout, almost all new carpeting and vinyl; and beautifully refinished hardwood floors. Few things left for your finishing touches. Celestory windows in great room with high ceilings beckon you in PLUS an eat-in kitchen and formal dining area or use as an office space. Lower level student or in-law suite possible. Totally finished. Has a br and full bath, and, there is an outside entrance. List of items repaired and or, upgraded will be included in the documents. Backyard is partially fenced but finish and put in a run-in shed or small barn and bring on the animals. Horses allowed. More pictures forthcoming. See floor plan for room layouts and measurements. Only 5 minutes to Leisure Acres common area for river access. Also, behind this house runs the lane to Dam #4! Ten minutes to downtown Shepherdstown, Shepherd University, restaurants and food shopping. Easy proximity to NCTC (the home of the US forest fish and wildlife) and a giant sycamore tree with a famous eagle nest visible from the road that can also be watched on eagle cam. This can be appealing to many young and adults... a nest Watch "Live! From the NCTC Eagle Nest - Camera 1" on YouTube.
#WVJF2019892

SHEPHERDSTOWN

79 LEISURE WAY

4 Beds

3 Baths

4,455 Sq.Ft.

$585,000

MLS#: WVJF2019892

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

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 on site today
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

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