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

54 Properties Found. Page 3 of 4.

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

None
#WVJF2015498

SHEPHERDSTOWN

332 W GERMAN STREET

None Beds

None Baths

0.29 acres

$219,900

MLS#: WVJF2015498

MOTIVATED SELLER Price Adjustment Shepherds Cove Potomac River Waterfront Community, Shepherdstown WV Lot 20 is an exceptional opportunity READY TO BUILD, beautiful wooded lot with well installed, lot has been cleared for house construction, community septic. Peaceful, tranquil setting. Shepherd Cove is a small , resort-like community of 19 lots with only 4 remaining. These large private lots have marina privileges, and private river access. Enjoy the beauty of nature in the wooded setting. Hiking trails and Biking paths boating, fishing, swimming, kayak and canoe. Marina with individual dock space available. Cress Creek Country club/golf club nearby. Private access to 12 navigable miles of the beautiful Potomac River. Community Pavilion overlooking the Potomac with outdoor kitchen, picnic gazebo, barbecue and fire pit. Bocce court and putting green. Away from it all yet convenient location. Minutes to downtown Shepherdstown, Shepherd University, boutique shops, good restaurants. An area of interesting folks, and cultural activities. Minutes to Marc commuter train to DC, 50 miles to Washington DC Beltway and Baltimore. Brochure provided in attached documents. For the person who has longed for a water oriented country escape that is both private and convenient, with woods and paths for nature walks, where deer, foxes, wild turkeys and eagles are abundant; this is the proverbial once in a lifetime opportunity. The opportunities for kayaking, fishing, hiking, boating and communing with nature are endless. Available Lots: Lot #2, 3.790 Acres, $195,000, Lot #5 3.98 Acres, $183,000 Lot #20, 4.356 Acres $209,,000 READY TO BUILD, Well installed, lot cleared,, Lot #9 5.3 acres LAST RIVER FRONT LOT Located on a bluff overlooking the Potomac BEAUTIFUL WOODED LOT, BEAUTIFUL BEAUTIFUL VIEWS up and down river $562,000,00. Property is in Berkeley County so no impact fee for construction.
#WVBE2033938

SHEPHERDSTOWN

Lot #20 SHEPHERDS COVE SWIFT RIVER WAY

None Beds

None Baths

4.36 acres

$209,000

MLS#: WVBE2033938

Motivated Seller Shepherds Cove Potomac River Waterfront Community, Shepherdstown WV Home Sites in a small , resort-like community. These the last 4 lots available in a community of 19 lots. Large private lots with marina privileges,. Enjoy the beauty of nature in the wooded setting. Hiking trails and Biking paths boating, fishing, swimming, kayak and canoe. Marina with individual dock space available. Country Private access to 12 navigable miles of the beautiful Potomac River. Community Pavilion overlooking the Potomac with outdoor kitchen, picnic gazebo, barbecue and fire pit. Bocce court and putting green. Away from it all yet convenient location. Minutes to downtown Shepherdstown, Shepherd University, boutique shops, good restaurants. An area of interesting folks, and cultural activities. Minutes to Marc commuter train to DC, 50 miles to Washington DC Beltway and Baltimore. Brochure provided in attached documents. For the person who has longed for a water oriented country escape that is both private and convenient, with woods and paths for nature walks, where deer, foxes, wild turkeys and eagles are abundant; this is the proverbial once in a lifetime opportunity. The opportunities for kayaking, fishing, hiking, boating and communing with nature are endless. Available Lots: Lot #2 3.790 Acres, $195,000, Lot #5 3.98 Acres, $183,000 Lot #20 4.35 acres $209,000 well installed, cleared for construction, ready to build , Lot9 LAST WATERFRONT LOT 5.3 acres BEAUTIFUL WOODED LOT, BEAUTIFUL BEAUTIFUL VIEWS on bluff overlooking the Potomac $592,000 Call for tour . Property is in Berkeley County so no impact fee for construction.
#WVBE2013862

SHEPHERDSTOWN

Lot #2 SHEPHERDS COVE SWIFT RIVER

None Beds

None Baths

3.79 acres

$195,000

MLS#: WVBE2013862

MOTIVATED SELLER Shepherds Cove Potomac River Waterfront Community, Shepherdstown WV Home Sites in a small , resort-like community. Hurry the last 4 lots available in a community of 19 lots. Large private lots with marina privileges,. Enjoy the beauty of nature in the wooded setting. Hiking trails and Biking paths boating, fishing, swimming, kayak and canoe. Marina with individual dock space , Private access to 12 navigable miles of the beautiful Potomac River. Community Pavilion overlooking the Potomac with outdoor kitchen, picnic gazebo, barbecue and fire pit. Bocce court and putting green. Away from it all yet convenient location. Minutes to downtown Shepherdstown, Shepherd University, boutique shops, good restaurants. An area of interesting folks, and cultural activities. Minutes to Marc commuter train to DC, 50 miles to Washington DC Beltway and Baltimore. Brochure provided in attached documents. For the person who has longed for a water oriented country escape that is both private and convenient, with woods and paths for nature walks, where deer, foxes, wild turkeys and eagles are abundant; this is the proverbial once in a lifetime opportunity. The opportunities for kayaking, fishing, hiking, boating and communing with nature are endless. Available Lots: Lot #2 3.790 Acres, $195,000, Lot #5 3.98 Acres, $183,000, LOT 20, $209, 000 READY TO BUILD, well installed, lot cleared for construction. Lot 9 5.3 ACRES $562,000.00 LAST WATERFRONT LOT Sits on bluff overlook the Potomac. BEAUTIFUL BEAUTIFUL VIEWS UP AND DOWN THE RIVER. Property is in Berkeley County so no impact fee for building.
#WVBE2013868

SHEPHERDSTOWN

Lot #5 SHEPHERDS COVE SWIFT RIVER WAY

None Beds

None Baths

3.39 acres

$183,000

MLS#: WVBE2013868

Tucked within one of the Eastern Panhandle’s most sought-after communities, Lot 107 on Reachcliff Drive presents a once-in-a-generation opportunity to build your custom home in Fernbank—known for its natural beauty, welcoming neighbors, and golf course setting. This lot provides 89' of frontage along the 5th fairway. Positioned at the highest elevation in the neighborhood, this wooded lot offers spectacular views of the Cress Creek Golf Course and protected countryside beyond. Located on a quiet cul-de-sac, Reachcliff Drive is prized for its peaceful atmosphere and refined homes valued up to $1M. With public water, sewer, and cable available, and a topography that supports a sunny walkout basement, this lot is ready for your architect and builder. The generous depth allows for privacy while still enjoying sweeping views and golf course access. Just minutes from the Potomac River, downtown Shepherdstown, and MARC commuter rail to DC, Fernbank offers an ideal blend of tranquility and convenience. Don’t miss your chance to own one of the premier homesites in the region.
#WVJF2019398

SHEPHERDSTOWN

REACHCLIFF DRIVE

None Beds

None Baths

0.66 acres

$179,500

MLS#: WVJF2019398

Are you wanting a piece of land with 400 ft of riverfront property in a private community just a few miles from the local town and shops? This 3.5 acre lot along the Potomac River has an array of opportunities waiting for you! This naturally, wooded lot provides the shade and privacy you may desire to enjoy during all seasons along with a bounty of wildlife. This land was previously perc'ed but has expired and will need to be perc'ed again if planning to build. The owners also had a driveway marked with green and yellow markers to be put in off of Steamboat Run Rd. You could keep the driveway entrance where they had it marked or in a new area of your preference. The land also has four markers in place to outline the property. No well or septic, all raw land for you to be able to start your very own project. This location is a flood hazard area within the FEMA 100-year floodplain. Please see the Steamboat Run Community Association website for detailed information regarding building and restrictions. Steamboat Run is a residential community and primarily for residential use only. Also, accompanied by this private community is a shared, open grassland, community recreation, and river access points that are pictured. This could make the perfect location for your dream home or weekend get away. You, don't want to miss out on this unique land space!
#WVJF2019444

SHEPHERDSTOWN

Lot 4A STEAMBOAT RUN ROAD

None Beds

None Baths

3.5 acres

$150,000

MLS#: WVJF2019444

You are in luck! This is one of the last remaining building lots in desireable Steamboat Run. Building site would be high, with a winter view of the river. Seller waiting for buyer to see where they would site the house and then once under contract, a perc test can be ordered. Property corners have been marked and staked with orange survey tape. This all wooded lot will not last!
#WVJF2019860

SHEPHERDSTOWN

STEAMBOAT RUN ROAD

None Beds

None Baths

2.2 acres

$143,500

MLS#: WVJF2019860

Build your dream home on this beautiful lot in the desirable riverfront community of Potomac River Farms. Recently perc’d for a class 2 septic system, this property offers a quiet country setting with a Shepherdstown address while being conveniently located in Berkeley County. Perfect for those who enjoy water recreation, the community river access is just around the curve at the end of the road—be sure to check it out when you visit! With its peaceful surroundings and minimal HOA fee, this is the ideal spot to create your own private retreat.
#WVBE2042662

SHEPHERDSTOWN

COMSTOCK DRIVE

None Beds

None Baths

2.61 acres

$139,900

MLS#: WVBE2042662

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