CHARIS REALTY GROUP
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SHEPHERDSTOWN

One of the most popular communities provided by Charis Realty Group - Christine Issler, Broker

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.

Connect with Us

  • Follow us on Facebook to stay updated.
  • 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.

One of the most popular communities provided by Charis Realty Group - Christine Issler, Broker
35
# of Listings
3
Avg # of Bedrooms
$294
Avg. $ / Sq.Ft.
$561,859
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

35 Properties Found. Page 2 of 3.

Overlooking Cress Creek Golf Club in Shepherdstown, this villa-style duplex offers a setting that feels peaceful, established, and easy to enjoy. Hardwood floors run throughout the main level, where the layout balances comfort and function with a formal dining room, an eat-in kitchen with table space, and a spacious living room centered around a wood burning fireplace with built-in shelving. A large bay window with window seat brings in natural light, and the covered porch extends the living space outdoors with a view of Cress Creek Golf Course, that adds something special to daily life. The upper level includes a primary suite with ensuite bath, a second bedroom, full hall bath, and stacked washer and dryer. On the walkout lower level, a private bedroom suite with full bath, walkthrough closet, and patio access creates flexible space for guests, hobbies, or extended stays. Complete with a 2-car attached garage, this 3 bedroom, 3.5 bath home combines a scenic golf course backdrop with a floor plan designed for comfort, privacy, and ease. All this with easy access to all the restaurants, culture, and community that Shepherdstown, WV has to offer, just an hour outside of Washington, DC.
#WVJF2023750

SHEPHERDSTOWN

20 DRENNEN COURT

3 Beds

3 Baths

2,295 Sq.Ft.

$525,000

MLS#: WVJF2023750

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

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

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.

$495,000

MLS#: WVJF2025730

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.

$495,000

MLS#: WVJF2026308

Charming Country Retreat nestled on a peaceful 1.63-acre private parcel along a quiet country road just outside historic Shepherdstown, this inviting 1963-built home offers the perfect blend of timeless character and versatile living space. With approximately 2500 total square feet, 3 bedrooms, and 2 bathrooms, this single-family residence sits on unrestricted land—ideal for those seeking freedom and flexibility in the Eastern Panhandle. Step inside to discover lovely hardwood flooring that flows throughout the main living areas, creating a warm and welcoming atmosphere. The spacious layout is filled with natural light and provides ample room for comfortable everyday living and entertaining. The finished basement presents exciting possibilities—easily transform it into a fourth bedroom, a creative hobby room, home office, or additional living space to suit your lifestyle. Outside, the property truly shines as a gardener's and nature lover's paradise. It's loaded with mature fruit trees, berry bushes, and an abundance of trees that provide privacy, shade, and seasonal beauty. A private deck off the back offers a serene spot to relax, enjoy the views, or entertain family and friends while surrounded by your own personal woodland setting. Conveniently located near Shepherdstown's vibrant arts scene, dining, and amenities, yet tucked away for privacy, this home is a rare find for those who appreciate country living with easy access to everything the area has to offer. Whether you're looking for a peaceful primary residence, a hobby farm setup, or a versatile property with room to grow, 561 Billmyer Mill Road delivers endless potential.
#WVJF2024604

SHEPHERDSTOWN

561 BILLMYER MILL ROAD

3 Beds

2 Baths

2,611 Sq.Ft.

$419,500

MLS#: WVJF2024604

Back on the market, buyer got called cold feet. Welcome to 207 Sandpiper Lane, a beautifully maintained, like new, 3-bedroom, 3-full-bath home situated on nearly one acre in desirable Shepherdstown, West Virginia. Built in 2018, this inviting property offers a thoughtful layout with generous living space and a fully finished walkout lower level. The main level offers an open floor plan, hardwood floors in the main living areas, a spacious living room, kitchen and dining area with access to the deck. The primary bedroom includes a full private bathroom. Two more nice size bedrooms and a 2nd full bathroom round out the main level. The lower level includes a spacious recreation room, 3rd full bathroom, laundry room and a door leading to the backyard. The home features a two-car side-load garage, adding both convenience and attractive curb appeal. You'll love entertaining on the 12' x 16' rear deck overlooking the beautiful backyard that backs to mature trees, creating a peaceful and private setting for relaxing and enjoying the outdoors. Conveniently located near historic charm of downtown Shepherdstown, this home offers the ideal combination of space, privacy, modern construction, and accessibility. Don’t miss the opportunity to make this exceptional Shepherdstown property your own!
#WVJF2025616

SHEPHERDSTOWN

207 SANDPIPER LANE

3 Beds

3 Baths

1,740 Sq.Ft.

$400,000

MLS#: WVJF2025616

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.

$399,000

MLS#: WVJF2024878

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.

$369,900

MLS#: WVJF2024134

This 2-unit duplex just outside Shepherdstown offers incredible flexibility and income potential. Whether you're an investor seeking a strong rental opportunity or an owner-occupant looking to offset your mortgage, this property checks all the boxes. Live in one unit and rent the other, or maximize income by leasing both. Ideal for those with students attending Shepherd University, this property provides a smart housing solution—live on-site while generating rental income from the second unit or additional bedrooms. Set on a large lot backing to trees, the outdoor space offers privacy and room to enjoy nature. Each unit features its own private driveway and parking area for added convenience. A storage building conveys, and the nicely landscaped yard enhances the property's overall appeal. Conveniently located with easy access to Route 45, this property combines peaceful surroundings with commuter-friendly accessibility.
#WVJF2022890

SHEPHERDSTOWN

202 OLD MARTINSBURG ROAD

5 Beds

None Baths

1,920 Sq.Ft.

$300,000

MLS#: WVJF2022890

Spacious, move-in ready, and just minutes from the heart of Shepherdstown! Welcome to 45 Ryan Court, a three-level townhome in the desirable Maddex Farm community offering approximately 1,900 square feet of finished living space, 3 bedrooms, 2 full baths, 2 half baths, and plenty of room to spread out. Step inside to a bright, open main level designed for easy everyday living and entertaining. The living and dining spaces flow naturally together, while the kitchen offers abundant cabinetry, generous workspace, and convenient access to outdoor living. Upstairs, retreat to the spacious primary suite with its own private en-suite bath. Two additional bedrooms and another full bath provide plenty of flexibility for family, guests, or a home office. Need even more space? The finished lower level adds an entire additional living area—perfect for a family room, home theater, game room, gym, office, or guest space—and includes an additional half bath. One of the best features of 45 Ryan Court is its location. Enjoy the charm and lifestyle of Shepherdstown without the maintenance and price point of many downtown properties. Restaurants, coffee shops, boutiques, Shepherd University, community events, the Potomac River, and C&O Canal Towpath are all just minutes away. Charles Town, Martinsburg, Harpers Ferry, and Maryland are also within easy reach. With nearly 1,900 square feet across three finished levels, multiple living spaces, four bathrooms, and a convenient Shepherdstown location, 45 Ryan Court offers a lot of home for the money. Whether you're a first-time buyer, downsizing, looking for a weekend home, or searching for an investment property, this one deserves a closer look. Come see how much space, flexibility, and convenience 45 Ryan Court has to offer!
#WVJF2025168

SHEPHERDSTOWN

45 RYAN COURT

3 Beds

2 Baths

1,750 Sq.Ft.

$299,900

MLS#: WVJF2025168

Unique Mixed-Use Opportunity! Rare corner lot offering residential, light industrial, and commercial zoning, providing exceptional flexibility for homeowners, investors, or business owners. The property features a cozy home ready for comfortable living along with a spacious shed ideal for storage, a workshop, or hobby space. High-visibility location with convenient access to Shepherdstown, Martinsburg, and major commuter routes. Whether you're looking for a live-work property, investment opportunity, or a site with future potential, this versatile property offers endless possibilities. Don't miss your chance to own this one-of-a-kind property with multiple permitted uses in a desirable location. Schedule your private showing today!
#WVJF2025646

SHEPHERDSTOWN

7628 MARTINSBURG PIKE

3 Beds

1 Baths

1,000 Sq.Ft.

$275,000

MLS#: WVJF2025646

New on site 1 day ago
Rare opportunity to own 5.68 beautiful acres just 1.5 miles from historic downtown Shepherdstown! This cleared, level homesite features open grassy fields and lovely views overlooking Cress Creek Golf Course. With a perc test already in hand, the property is ready for you to begin planning your dream home, gentleman’s farm, garden, or private retreat. Enjoy the peaceful setting while remaining close to Shepherd University, shopping, dining, outdoor recreation, and a commuter rail station. Privacy, views, acreage, and an incredible location—this special property offers the perfect opportunity to create the lifestyle you have been dreaming of!
#WVJF2026372

SHEPHERDSTOWN

5.68AC SHEPHERD GRADE RD

None Beds

None Baths

5.68 acres

$250,000

MLS#: WVJF2026372

Nestled on an expansive 5.96-acre canvas, in the private, gated community Shepherds Cove, this exceptional land opportunity offers a rare blend of natural beauty and luxurious potential. Imagine crafting your dream home surrounded by the serene embrace of towering trees and lush woods, where every sunrise and sunset paints the sky in breathtaking hues. The phenomenal sellers have crafted a true masterpiece in a "modern colonial" with expansive windows throughout. They are graciously offering to convey the house plans they created in conjunction with a local drafting company at closing. The plan was brought to life for this specific lot in mind lending itself to take in the picturesque native spring wildflowers, stone outcroppings, and lush wooded backdrop (see listing photos for illustration of house rendering). Shepherds Cove boasts exclusive community access to the Potomac River, inviting you to indulge in a lifestyle defined by tranquility and adventure. Where you can enjoy leisurely afternoons kayaking, fishing, or simply soaking in the peaceful ambiance that a riverfront location can provide. The gentle sounds of flowing water and the rustle of leaves create a symphony of nature that enhances the sense of home and comfort. The expansive nearly 6 acre lot is amongst the largest in the 19-lot community and offers ample space for your vision, whether it be a luxurious estate, a charming cottage, or a modern masterpiece. The possibilities are endless, allowing you to design a residence that reflects your personal style while harmonizing with the natural surroundings. Outdoor living spaces include a community riverfront pavilion with a kitchen/BBQ space, long meandering community hiking trails, gazebo, fire pit, bocce court, and marina storage space that seamlessly blend with the landscape, where you can entertain guests or unwind in solitude, all while enjoying the stunning views of the woods & river that envelop you. The proximity to the Potomac River enhances the allure, providing a perfect backdrop for outdoor activities and a peaceful retreat from the hustle and bustle of everyday life. With nearly 12 miles of navigable waters just steps away at the community river access, you can explore the river's beauty at your leisure, creating cherished memories. The lush greenery and natural features of the land offer a sense of privacy and seclusion, making it an ideal sanctuary where every day feels like a getaway. This is more than just land; it's a canvas for your dreams, a place where you can cultivate a lifestyle that celebrates the beauty of nature and the comforts of home. Discover the potential that awaits you in this extraordinary property, where luxury meets the great outdoors all within 1.5 hours of DC, Baltimore, MD, and Northern Virginia and in close proximity to MARC commuter train locations. Outside of the community, a leisurely stroll on the 184.5 mile C & O Canal Towpath, membership options at Cress Creek Golf Club or dining & entertainment options downtown Shepherdstown are all waiting to be explored. Nearby Shepherd University offers a range of activities to the community including a Wellness Center, the Life Long Learning program, as well as athletic events, concerts, lectures and plays throughout the year. Living in Shepherdstown embraces a lifestyle filled with community and local charm which was emphasized by its recognition as a 2026 recipient of the USA TODAY Readers’ Choice Top 10 Award for Best Historic Small Towns. Reach out today to gain access to explore this wonderful land opportunity!
#WVBE2050696

SHEPHERDSTOWN

SWIFT RIVER WAY, LOT 6

None Beds

None Baths

5.96 acres

$215,000

MLS#: WVBE2050696

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