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$550,000
3 Beds ⋅ 2 Baths
Charming brick home located just outside of town limits and moments from the heart of historic Shepherdstown. This 3-bedroom, 1.5-bath residence offers approximately 1,592 square feet of living space, a full unfinished basement, fireplace, and a spacious lot with room to enjoy outdoor living. From the front porch to the back porch, this home is filled with character. Conveniently located near local shops, restaurants, Shepherd University, and the Potomac River, this property combines classic character with everyday convenience in one of West Virginia's most sought-after small towns.

416 S Church St, Shepherdstown

Listing courtesy of Path Realty. Contact: 3042796950
$665,000
4 Beds ⋅ 3 Baths
Why Wait for New? Welcome to 91 Marsh Hawk Way, Shepherdstown, WV—an exceptional Craftsman Colonial home situated on a beautiful 1-acre home site, offering the perfect combination of elegance, space, and modern comfort. Built in 2022, this stunning 4-bedroom, 2.5-bath home features 2,684 square feet of thoughtfully designed living space with quality finishes throughout. Rich hardwood floors enhance the main level, while the open-concept floor plan is ideal for both everyday living and entertaining. The beautifully appointed kitchen showcases stainless steel appliances, abundant cabinetry, generous granite counter space, cooktop, wall oven and a large center island that flows seamlessly into the spacious family room and dining area. Upstairs, the impressive primary suite serves as a private retreat, featuring a spacious bedroom, a luxurious ensuite bath with a soaking tub, separate shower, dual vanities, and ample closet space. Three additional bedrooms and a full bath provide plenty of room for family, guests, or a home office. This residence offers exceptional craftsmanship, stylish finishes, and modern energy-efficient construction. The expansive 1-acre lot provides endless opportunities for outdoor entertaining, gardening, recreation, or simply enjoying the peaceful surroundings. Conveniently located just minutes from historic downtown Shepherdstown, local restaurants, shopping, parks, schools, and major commuter routes, this move-in-ready home offers the ideal balance of luxury, comfort, and convenience. Don't miss your opportunity to own this beautifully maintained home that truly stands out from the rest. Schedule your private showing today!

91 Marsh Hawk Way, Shepherdstown

Listing courtesy of Young & Associates. Contact: (304) 707-0086
$589,000
4 Beds ⋅ 4 Baths
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.

262 Canal Way, Shepherdstown

Listing courtesy of Samson Properties. Contact: 3049305621
$310,000
3 Beds ⋅ 4 Baths
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.

45 Ryan Ct, Shepherdstown

Listing courtesy of Samson Properties. Contact: 3049305621
$324,000
3 Beds ⋅ 4 Baths
Welcome to this Convenient 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! PRICE REDUCED & SELLER OFFERS BUYER A $5,000 CREDIT AT CLOSING. 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.

39 Swearingen Way, Shepherdstown

Listing courtesy of Snyder Bailey & Associates. Contact:

$425,000
3 Beds ⋅ 1 Baths
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.

17 Old Prospect Ave, Shepherdstown

Listing courtesy of Path Realty. Contact: 3042796950
$575,000
4 Beds ⋅ 4 Baths
Move In Ready, 4 bed, 3.5 bath Farmette on 2.25 Unrestricted acres in Shepherdstown. This home has many updates including a NEW ROOF, 2 New HVAC Units, New Hot Water Heater, New bathrooms with custom tile and quartz tops, New LVP flooring, fresh paint from top to bottom, New hardware and fixtures. The brand new kitchen features stainless steel appliances and quartz counter tops. Other features include: 3 bedrooms on the upper level, and 1 bedroom/home office on the main level, a front and rear covered porch, an oversized 2 car garage, a barn, and a fully finished basement.

637 Persimmon Ln, Shepherdstown

Listing courtesy of Freedom Real Estate Group, LLC.. Contact: (304) 279-4162
$515,000
4 Beds ⋅ 4 Baths
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.

65 Maddex Farm Drive, Shepherdstown

Listing courtesy of Greentree Associates of Shepherdstown, Inc.. Contact: 304-876-3737
$420,000
3 Beds ⋅ 3 Baths
Don't let first looks fool you!  This 3 bedroom, 2.5 bathroom contemporary home is move-in ready and designed for easy living.  The open floor plan features easily accessible entry-level living, two upstairs guest bedrooms, and a full walkout basement.  In 2026 the owners installed a new roof with 30 year architecture singles; renovated the kitchen with new appliances, painted the cabinets, and installed modern hardware; installed new carpet in each bedroom and LVP in the bathrooms.  Set just moments from the town center, the property features a private deck with motorized awning, a secluded patio which backs to trees, and nearby pathways leading to Shepherd University's Wellness Center and the historic downtown Shepherdstown.  The hybrid floor plan features the updated kitchen space connecting to an open dining and living 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 that share a guest bath upstairs. A finished walkout basement provides great versatility with an additional half bathroom and flexible living space.  This original section of the Maddex Farm community features mature landscaping and has great accessibility to Shepherdstown, one of the nation's Best Historic Small Towns (2026 USA Today).

122 Hensel Dr, Shepherdstown

Listing courtesy of Coldwell Banker Premier. Contact:

$579,900
5 Beds ⋅ 4 Baths
Price Improvement! Stunning 5-bedroom, 3.5-bath Colonial tucked away on a private half-acre lot backing to mature trees in the sought-after Willow Springs Acres community of Shepherdstown, WV. Offering spacious living across three finished levels, this home combines timeless style, functional design, and peaceful outdoor living. Step inside to a dramatic 2-story foyer flanked by a private home office and elegant formal living room that seamlessly flows into the formal dining room—perfect for entertaining. The spacious eat-in kitchen is the heart of the home and features granite countertops, new stainless-steel appliances, a center island with breakfast bar seating, pantry, and sunny dining area. The kitchen opens to the expansive family room highlighted by a cozy wood stove and direct access to the screened-in porch overlooking the tree-lined backyard. A convenient half bath and laundry room complete the main level. Upstairs, the spacious primary suite offers a large walk-in closet and private en suite bath featuring dual vanities, a soaking tub, and separate shower. The additional bedrooms are all nicely sized, with Bedrooms 3 and 4 connected by a Jack-and-Jill bathroom for added convenience and functionality. The mostly finished lower level provides exceptional flexibility with a large recreation room, 5th bedroom, full bath, and abundant storage space—ideal for guests, multi-generational living, hobbies, or a home gym. Additional highlights include a side-entry 2-car garage, oversized driveway with ample parking, open-concept layout, and a serene backyard setting with added privacy. Conveniently located near historic Shepherdstown, commuter routes, dining, shopping, and outdoor recreation.

49 Appomattox Ln, Shepherdstown

Listing courtesy of Dandridge Realty Group, LLC. Contact: 3048857645
$687,000
5 Beds ⋅ 5 Baths
SELLER MOTIVATED! Don’t lose the opportunity to own this AMAZING BREATHTAKING VIEWS! on a property located in one of the nicest subdivisions in Jefferson County. Amazing views from all windows, Home over 5,600 finished square feet. Kitchen with updated stainless appliances, breakfast area adjacent to living room. Beautiful wood floors throughout most of the house. Basement has a bedroom and full bath, large rec room, gym area and plenty of storage. Rear deck off the living room backs to orchard and walking trail. Extensive hardscape, stone retaining wall, and rear patio off basement, bonus room. NEW SECURITY SISTEM 4 Cameras around the house. 5 K in BLINDS. A/C and Heat WITH DUAL type of fuel ROOF AROUND 3 years old. Must see.

48 Field Crest Ct, Shepherdstown

Listing courtesy of Spring Hill Real Estate, LLC.. Contact: 7038914520