CHARIS REALTY GROUP
SHEPHERDSTOWN community

SHEPHERDSTOWN Real Estate

Explore properties and local insights in SHEPHERDSTOWN.

About SHEPHERDSTOWN

About SHEPHERDSTOWN

Shepherdstown, WV Real Estate and Community

Welcome to Shepherdstown, West Virginia

Discover the charm and allure of Shepherdstown, a historic town nestled in the Eastern Panhandle of West Virginia. With its rich heritage and vibrant community, Shepherdstown offers an exceptional quality of life alongside diverse real estate opportunities.

Why Live in Shepherdstown?

A Rich History

  • Founded in 1734, Shepherdstown is one of the oldest towns in West Virginia.
  • Home to significant historical landmarks, such as the Shepherd University and the Antietam National Battlefield.

Vibrant Community Life

  • Enjoy a tight-knit community with friendly neighbors and local events.
  • Participate in year-round activities like the Shepherdstown Street Fest, art openings, and farmers’ markets.

Natural Beauty

  • Surrounded by stunning landscapes, including the Potomac River and nearby Appalachian Mountains.
  • Ideal for outdoor enthusiasts: hiking, biking, and fishing abound in the area.

Real Estate in Shepherdstown

Diverse Property Options

  • Single-family homes: Ranging from historic charm to modern designs.
  • Condos and townhomes: Perfect for those seeking low-maintenance living.
  • Vacant land: Opportunities to build your dream home amidst nature.

Market Insights

  • Shepherdstown boasts a competitive real estate market, making it ideal for buyers and investors alike.
  • Home prices typically range from $200,000 to over $1 million, catering to various budgets.

Why Invest Now?

  • Growing demand: With its proximity to Washington, D.C., Shepherdstown attracts professionals looking for a quieter lifestyle while maintaining access to urban amenities.
  • Strong community values: Invest in a town that prioritizes its residents and fosters a welcoming environment.

Explore Shepherdstown’s Real Estate Today

Ready to find your dream home in Shepherdstown?

  • Contact us for expert guidance on navigating the local real estate market.
  • Visit our website for the latest listings and market updates.

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  • Sign up for our newsletter for insider tips and community news.

Join us in discovering the beauty and potential of Shepherdstown, WV! Your new home awaits.

SHEPHERDSTOWN community
43
# of Listings
3
Avg # of Bedrooms
$280
Avg. $ / Sq.Ft.
$526,109
Med. List Price

Homes for Sale in SHEPHERDSTOWN

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.

Nestled in the serene Willow Springs Acres, this charming Colonial home offers a perfect blend of comfort and elegance. With 5 spacious bedrooms and 3.5 bathrooms, this residence is designed for both relaxation and entertaining. Step inside to discover an inviting open floor plan adorned with crown moldings and chair railings, creating a warm ambiance throughout. The heart of the home is the beautifully appointed kitchen, featuring upgraded countertops, a convenient island, and stainless steel appliances, including a double oven and cooktop. Enjoy casual meals in the breakfast area or host formal dinners in the separate dining room. The family room, complete with a cozy wood stove, flows seamlessly from the kitchen, making it ideal for gatherings. Retreat to the primary suite, where you'll find a luxurious bathroom with a soaking tub and walk-in shower, providing a spa-like experience at home. Additional highlights include a partially finished basement, perfect for a home office or play area, and a laundry room conveniently located on the main floor. Outside, the expansive 0.52-acre lot backs to lush trees, offering privacy and a picturesque view of the garden and woods. Enjoy evenings on the patio or porch, surrounded by nature. The property also features an attached side-entry garage and a paved driveway for ample parking. This home is not just a place to live; it's a sanctuary where memories are made. Experience the perfect blend of comfort, style, and tranquility in this delightful residence.
#WVJF2026538

SHEPHERDSTOWN

49 APPOMATTOX LANE

5 Beds

3 Baths

3,950 Sq.Ft.

$579,900

MLS#: WVJF2026538

Major price improvement! This property is listed as a commercial listing under MLS# WVJF2020060 and multi-family property under MLS# WVJF2023040. 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!
#WVJF2023042

SHEPHERDSTOWN

104 E GERMAN STREET

5 Beds

None Baths

4,416 Sq.Ft.

$579,900

MLS#: WVJF2023042

Major price improvement! This property is listed as a commercial listing under MLS# WVJF2020060 and multi-family property under MLS# WVJF2023040. 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 E GERMAN STREET

None Beds

None Baths

4,416 Sq.Ft.

$579,900

MLS#: WVJF2020060

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

Discover the epitome of luxury living in this exquisite new construction ranch-style home, set to be completed in 2027. Nestled on a sprawling 2.01-acre lot in a serene rural setting, this residence offers an exclusive lifestyle that harmonizes modern elegance with the tranquility of nature. Step inside to find a thoughtfully designed layout featuring three spacious bedrooms and two full bathrooms, perfect for both relaxation and entertaining. The heart of the home boasts a stunning kitchen equipped with high-end stainless steel appliances, including a built-in microwave, electric oven/range, and a sleek refrigerator, ensuring culinary excellence at your fingertips. The open-concept living area is enhanced by a cozy gas fireplace, creating a warm ambiance for gatherings. Enjoy the convenience of main-floor laundry and an attached three-car garage, providing ample space for vehicles and storage. The luxurious finishes extend to the flooring, featuring elegant ceramic tile and luxury vinyl plank, combining style with durability. With no association amenities, you have the freedom to create your own outdoor oasis. The expansive lot offers endless possibilities for landscaping or outdoor entertainment. Experience the charm of rural living while being just a short drive from urban conveniences. This property is not just a home; it's a lifestyle choice that embodies comfort, sophistication, and the promise of cherished memories. Embrace the opportunity to make this dream home your own.
#WVBE2054614

SHEPHERDSTOWN

Lot B17 CEDAR LANE

3 Beds

2 Baths

1,797 Sq.Ft.

$559,900

MLS#: WVBE2054614

Large Price Improvement!!! Welcome to 262 Canal Way, Shepherdstown, WV, where thoughtful upgrades and an exceptional location come together in one beautiful home. Nestled in one of Shepherdstown's most desirable neighborhoods, this spacious residence offers the perfect blend of elegance, comfort, and functionality. Step inside to find beautiful hardwood floors flowing throughout the main living areas, creating a warm and inviting atmosphere. The open-concept design is ideal for both everyday living and entertaining, centered around a gourmet kitchen featuring an oversized center island, double wall ovens, abundant cabinetry, and generous prep space. Comfort-height kitchen and bathroom countertops add a touch of luxury and convenience throughout the home. Upstairs, the private primary suite serves as a peaceful retreat, complete with a spacious en suite bathroom and generous walk-in closets, offering comfort, privacy, and ample storage. Additional bedrooms provide flexible space for family, guests, or a home office. The finished lower level expands the home's versatility with a stunning floor-to-ceiling stone fireplace that creates a warm, cozy gathering space. A wet bar rough-in is already in place, making it easy to design the entertainment area of your dreams—whether it's a game room, media room, home gym, or guest suite. Thoughtful details throughout the home include ceiling fans in most rooms, a central vacuum system for added convenience, and quality finishes designed for comfortable everyday living. Major updates—including a roof replaced in 2020 and an HVAC system replaced in 2021—provide added value and peace of mind for years to come. Located just minutes from historic downtown Shepherdstown, you'll enjoy easy access to charming boutiques, award-winning restaurants, coffee shops, parks, walking trails, the Potomac River, and the C&O Canal Towpath. Convenient commuter routes to Charles Town, Martinsburg, Maryland, and Northern Virginia make this location as practical as it is picturesque. Beautifully maintained, tastefully upgraded, and ideally located, 262 Canal Way offers the opportunity to enjoy everything that makes Shepherdstown one of the Eastern Panhandle's most sought-after places to call home. Schedule your private showing today and experience it for yourself!
#WVJF2025190

SHEPHERDSTOWN

262 CANAL WAY

4 Beds

2 Baths

4,530 Sq.Ft.

$559,000

MLS#: WVJF2025190

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

Nestled in the charming Fernbank community, this delightful twin home offers a perfect blend of comfort and convenience. Built in 1999, this villa-style residence features 3 spacious bedrooms and 2 full bathrooms, providing ample space for relaxation and gatherings. The fully finished daylight basement adds versatility, perfect for a home office or entertainment area. Enjoy serene views of the nearby golf course from your backyard, creating a peaceful retreat right at home. The 0.38-acre lot provides plenty of outdoor space for gardening or leisure activities. With an attached garage and driveway parking, convenience is at your fingertips. Fernbank is known for its welcoming atmosphere, with nearby parks and recreational facilities that encourage an active lifestyle. Local schools are highly regarded, ensuring quality education for all. The community also benefits from efficient public services, including snow removal, making winter months hassle-free. Experience the warmth of this neighborhood and make this lovely property your new home!
#WVJF2026308

SHEPHERDSTOWN

260 FERNBANK DRIVE

3 Beds

2 Baths

2,376 Sq.Ft.

$450,000

MLS#: WVJF2026308

Historic Shepherdstown Villa – Spacious, Flexible Living! Located in historic Shepherdstown, WV, this well-appointed villa offers 4 bedrooms, 3 full bathrooms, and plenty of space for comfortable living and entertaining. The versatile floor plan features 2 bedrooms on the main level and 2 additional bedrooms on the lower level, making it ideal for guests, a home office, or extended living arrangements. The main level offers an eat-in kitchen, formal dining room, and spacious living room, along with a primary bedroom featuring a private bath and walk-in closet. Step outside to enjoy the rear deck, perfect for relaxing or entertaining. The lower level provides additional living space with a recreation room, two bedrooms, and a full bathroom, large laundry and separate utility room for storage plus convenient access to the rear patio. Situated on a corner lot, the property also features a 2-car garage and paved driveway. New roof and gutters coming in October, 2026! A great opportunity to enjoy the comfort and convenience of villa living in the charming and historic Shepherdstown area!
#WVJF2026614

SHEPHERDSTOWN

43 BON AIRE DRIVE

4 Beds

3 Baths

2,500 Sq.Ft.

$449,900

MLS#: WVJF2026614

Multi-unit Property! Unique opportunity in the heart of Shepherdstown! This versatile property features two separate living spaces under one roof, each with its own kitchen, making it ideal for multi-generational living, in-law suite, rental income potential, or owner-occupancy with additional living quarters. Keep units separate or combine them back together to create a larger single residence. Enjoy private rear porches overlooking the backyard, providing inviting outdoor space for relaxing or entertaining. Conveniently located near downtown Shepherdstown, Shepherd University, shopping, dining, and local amenities.
#WVJF2025730

SHEPHERDSTOWN

7 OLD PROSPECT AVENUE

4 Beds

2 Baths

2,146 Sq.Ft.

$425,000

MLS#: WVJF2025730

Discover the charm of this beautifully renovated Cape Cod home nestled in the desirable Maddex Farm community. With a major renovation completed in 2026, this residence boasts an excellent condition and upgrades throughout. The upgraded countertops and luxury vinyl plank flooring add a touch of elegance, while the breakfast area invites casual dining. This home features three comfortable bedrooms, including a main level primary en-suite with a walk-in closet, ensuring ample storage. Outside, the lot is situated on a peaceful cul-de-sac, providing a safe environment for outdoor activities. Across the street is community common space with a wooded stream area and just across from the intersection of Oatfield and Hensell is the community playground and picnic area. The community offers fantastic amenities, including basketball courts, playgrounds, and a paved walking path to the Shepherd University grounds at the Wellness Center. Using this path, literally 200 yards from your home, you can access safe travel to Shepherd University, downtown Shepherdstown, and the C and O Canal, all within walking or biking distance. With an attached garage and paved driveway, parking is a breeze.
#WVJF2024134

SHEPHERDSTOWN

35 OATFIELD COURT

3 Beds

2 Baths

1,536 Sq.Ft.

$349,900

MLS#: WVJF2024134

Charming home just outside of town limits. Walking distance to downtown Shepherdstown with convenient access to local restaurants, shops, parks, and the University. This residence features a welcoming atmosphere with spacious living areas, abundant natural light, and lots of character. Enjoy outdoor living with a beautiful back yard and mature landscaping. Close to commuter routes while maintaining the charm and tranquility of one of West Virginia's most sought-after historic communities.
#WVJF2024878

SHEPHERDSTOWN

17 OLD PROSPECT AVENUE

3 Beds

1 Baths

1,560 Sq.Ft.

$330,000

MLS#: WVJF2024878

New on site 1 day ago
Welcome to this delightful ranch-style home nestled just outside Shepherdstown. Built in 1968, this brick residence offers 1,176 sq. ft. of comfortable living space, featuring a full basement and three spacious bedrooms and a full bathroom. The expansive 0.46-acre lot provides ample outdoor space for gardening, play, or relaxation. The neighborhood is known for its strong sense of community, with nearby parks perfect for outdoor activities and leisurely strolls. Enjoy the convenience of off-street parking and a driveway, making access a breeze. With its blend of classic design and modern potential, this home is a perfect canvas for your personal touch. Experience the vibrant community spirit and local amenities that make Shepherdstown a wonderful place to call home. Don't miss this opportunity to embrace a lifestyle of comfort and convenience!
#WVJF2026758

SHEPHERDSTOWN

7464 MARTINSBURG PIKE

3 Beds

2 Baths

1,176 Sq.Ft.

$270,000

MLS#: WVJF2026758

New on site 1 day ago
Nestled in the charming Mecklenburg Heights close to downtown Shepherdstown where you can enjoy dining and shopping, This nice ranch-style home includes a full walkout basement. With three spacious bedrooms and one and a half baths, the traditional floor plan invites you to create lasting memories. The country-style kitchen, complete with eat-in space, is perfect for casual gatherings, featuring appliances including an electric oven/range and a front-loading washer and dryer for your convenience. inviting atmosphere. The full basement offers endless possibilities for customization, whether you envision a cozy retreat or a vibrant entertainment space. Outside, the generous 0.24-acre lot provides ample room for outdoor activities or serene relaxation on the raised platform serving as mini wooden deck. Experience the lifestyle this home offers, blending comfort with functionality in a sought-after neighborhood.
#WVJF2026902

SHEPHERDSTOWN

523 SANDPIPER LANE

3 Beds

1 Baths

1,056 Sq.Ft.

$265,000

MLS#: WVJF2026902

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