CHARIS REALTY GROUP
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SHEPHERDSTOWN

One of the most popular communities provided by Charis Realty

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
50
# of Listings
3
Avg # of Bedrooms
$317
Avg. $ / Sq.Ft.
$544,069
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

50 Properties Found. Page 3 of 4.

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

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.

$429,990

MLS#: WVJF2020720

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

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. Motivated seller
#WVBE2033938

SHEPHERDSTOWN

Lot #20 SHEPHERDS COVE SWIFT RIVER WAY

None Beds

None Baths

4.36 acres

$209,000

MLS#: WVBE2033938

``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 Motivated seller
#WVBE2013862

SHEPHERDSTOWN

Lot #2 SHEPHERDS COVE SWIFT RIVER

None Beds

None Baths

3.79 acres

$195,000

MLS#: WVBE2013862

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. Motivated seller
#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

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

Scenic 2.07-Acre Residential Raw Land Homesite in Shepherdstown Discover the perfect blend of privacy, location, and opportunity with this 2.07-acre residential vacant lot tucked just off Shepherd Lane in Shepherdstown, West Virginia. Set within an established neighborhood of well-spaced homes, this rolling, wooded parcel offers an ideal setting for a custom home surrounded by nature while remaining minutes from town. The property features gentle topography, mature trees, and a private feel, with clearly defined boundaries and neighboring homes that reinforce long-term residential use. With over 90,000 square feet, there’s ample room for a thoughtfully designed residence, outdoor living spaces, gardens, or additional structures—subject to county approvals. Conveniently located near historic downtown Shepherdstown, Shepherd University, the C&O Canal, and the Potomac River, this lot offers easy access to dining, culture, outdoor recreation, and commuter routes—making it equally attractive for a primary residence or future investment. Bring your builder and your vision—this is a rare opportunity to secure usable acreage in one of Jefferson County’s most desirable areas.
#WVJF2019244

SHEPHERDSTOWN

Lot 8-6.1 SHEPHERD LANE

None Beds

None Baths

2.07 acres

$140,000

MLS#: WVJF2019244

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

Prime real estate offering high visibility and robust traffic count, making it the perfect location for your business. Situated on a corner lot with dual access from Martinsburg Pike and Old Martinsburg Road, this property offers a surplus of parking spaces. Ideal for medical or professional offices. Tenants are responsible for any improvements required to create their ideal workspace. Featuring 3870 square feet (auditorium side) of customizable space, lease the entire 7600 square feet main floor (lease price is based on $15/sq ft plus NNN). The landlord is open to a five-year lease agreement, ensuring stability for your business.
#WVJF2016146

SHEPHERDSTOWN

7595 MARTINSBURG PIKE A

None Beds

None Baths

N/A

$6,450

MLS#: WVJF2016146

Prime real estate offering high visibility and robust traffic count, making it the perfect location for your business. Situated on a corner lot with dual access from Martinsburg Pike and Old Martinsburg Rd, this property offers a surplus of parking spaces. Ideal for medical or professional offices. Tenants are responsible for any improvements required to create their ideal workspace. Featuring 2,000 square feet of space, including five private offices or rooms, a generous 16x19 reception area, two separate restrooms or powder rooms, make it an excellent choice for a variety of businesses. The landlord is open to five year lease agreement, ensuring stability for your business.
#WVJF2016144

SHEPHERDSTOWN

7595 MARTINSBURG PIKE D

None Beds

None Baths

N/A

$3,350

MLS#: WVJF2016144

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