CHARIS REALTY GROUP
One of the most popular communities provided by {{page_data.agentName}}

SHEPHERDSTOWN

One of the most popular communities provided by Charis Realty Group

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
34
# of Listings
3
Avg # of Bedrooms
$257
Avg. $ / Sq.Ft.
$573,770
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

34 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.

$535,000

MLS#: WVJF2023750

As soon as you enter this beautiful home you realize this is a well maintained one! Nice open stairway and two-story foyer to the second floor. Sparkling wood floors and laminate floors as well. First floor offers living room as well as a family room off the kitchen. Formal dining but breakfast room also and, counter seating in a beautifully laid out kitchen. Granite counters, gas stove, built in microwave, oversized refrigerator and matching dishwasher. Breakfast room has lots of windows and wonderful sunlight coming in. Dark laminate floor flows nicely and easy clean. Only steps away to a large paved patio area and wrought iron fenced backyard. Yard backs to one of the common areas, allowing nice privacy in the rear as well as additional play yard! All four of the upstairs bedrooms are carpeted. Primary bedroom is extra large with an ensuite bath with separate tub and shower. The primary bedroom closet has custom built- in shelving. Another bath off the other 3 bedrooms rounds out the second floor. Downstairs finds a large finished area which could be playroom, office, hobby or even an extra bedroom. A half bath services that area and an outside walkup entrance. Lots of updated lighting and ceiling fans. New roof in 2025, new HW heater, 8 yr. old heat pump, and paneled garage door! Guardian alarm system and Ring cameras. Minutes to the grocery store, pharmacy, gas stations and restaurants! 5 minutes from downtown historic Shepherdstown and Shepherd University (walking/biking path to Shepherd in the neighborhood!) Be at the Antietam Battlefield in 10 minutes and Harpers Ferry in 20 minutes. And, lots of outdoor activities from hiking, and fishing and boating on the Potomac River.
#WVJF2024326

SHEPHERDSTOWN

65 MADDEX FARM DRIVE

4 Beds

2 Baths

3,902 Sq.Ft.

$515,000

MLS#: WVJF2024326

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

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.

$439,000

MLS#: WVJF2024604

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.

$425,000

MLS#: WVJF2024878

Main level living never looked so easy in this newly renovated and move-in ready contemporary home in the desirable Maddex Farm community with its connecting pathways to the town and University. Brand new architectural shingle roof, freshly painted with hardwood floors, and new carpet in the bedrooms and luxury vinyl tile in the bathrooms - this home has been renovated on all levels, inside and out! The hybrid floor plan features an updated kitchen space with brand new appliances, connecting to an open dining and family room with beautiful vaulted ceilings, a balcony overlook, and a sliding glass walkout to the refinished deck and private backyard. There's a primary bedroom and bathroom suite on the main floor and two guest bedrooms, with cubby hole storage, that share a guest bath upstairs. A finished walkout basement provides great versatility with an additional half bathroom and flexible living space. A HUGE storage room highlights the lower level. This original section of the Maddex Farm community has great accessibility to all Shepherdstown offers with mature landscaping and shade trees.
#WVJF2024250

SHEPHERDSTOWN

122 HENSEL DRIVE

3 Beds

2 Baths

1,754 Sq.Ft.

$420,000

MLS#: WVJF2024250

Price Improvement! Premier, three-level, corner lot townhome located 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!
#WVJF2024452

SHEPHERDSTOWN

420 STARKEYS LANDING

4 Beds

2 Baths

2,880 Sq.Ft.

$348,000

MLS#: WVJF2024452

Welcome to this Sun-Drenched and Spacious Townhome with Brick Façade, Serene Wooded Views, 3 Bedrooms, 2 Full Bathrooms, and 2 Half Baths. Recent updates include Refinished Hardwood Floors, Newly Installed Redefined Pine Floors, recent New Deck Floor Boards, and an almost new HVAC System that was installed in 2024. Comcast cable and Xfinity are available. Enjoy the perfect blend of town and country! This home is conveniently located near the new Shepherdstown Library, Morgan’s Grove Park, and the unique restaurants and shops of historic downtown Shepherdstown. Your options for adventure are nearly endless, with the Potomac River, C&O Canal, Harpers Ferry, Charles Town, Martinsburg, the Appalachian Trail, and lots of Outdoor Recreation with MARC commuter and Amtrak passenger train stations in the area. Visit https://shepherdstown.info/ for more information, to request the email newsletter, and to view the calendar of local events.
#WVJF2024904

SHEPHERDSTOWN

39 SWEARINGEN WAY

3 Beds

2 Baths

2,220 Sq.Ft.

$329,000

MLS#: WVJF2024904

New on site 1 day ago
Welcome to 45 Ryan Court, where low-maintenance living meets the charm and character of historic Shepherdstown. Nestled in the desirable Maddex Farm community, this spacious three-level townhome offers approximately 1,900 square feet of comfortable living space with 3 bedrooms, 2 full baths, and 2 half baths. The inviting main level features a bright, open floor plan that seamlessly connects the living and dining areas, creating an ideal space for everyday living and entertaining. The kitchen offers ample cabinetry and workspace with easy access to outdoor living. Upstairs, the spacious primary suite provides a private retreat complete with an en-suite bath, while two additional bedrooms offer flexibility for family, guests, or a home office. The finished lower level expands your living space and is perfect for a recreation room, media room, fitness area, or work-from-home setup, complete with an additional half bath. Enjoy the convenience of living just minutes from downtown Shepherdstown, where you'll find locally owned restaurants, coffee shops, boutiques, and year-round community events. Outdoor enthusiasts will appreciate nearby walking trails, parks, the Potomac River, and easy access to the C&O Canal Towpath. Commuters will enjoy convenient access to Charles Town, Martinsburg, Harpers Ferry, and Maryland and Northern Virginia. Whether you're looking for your first home, a weekend getaway, or an investment opportunity, this move-in-ready townhome offers the perfect combination of comfort, convenience, and the unique lifestyle that makes Shepherdstown one of West Virginia's most sought-after communities.
#WVJF2025168

SHEPHERDSTOWN

45 RYAN COURT

3 Beds

2 Baths

1,750 Sq.Ft.

$325,000

MLS#: WVJF2025168

None
#WVJF2021398

SHEPHERDSTOWN

19 CARDINAL DRIVE

3 Beds

1 Baths

1,352 Sq.Ft.

$309,000

MLS#: WVJF2021398

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

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

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 3 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 may be 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, Great restaurants. An area of interesting folks, and cultural activities. Minutes to Marc commuter train to DC, 50 miles to Washington DC 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

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