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SHEPHERDSTOWN

One of the most popular communities provided by Charis Realty

SHEPHERDSTOWN

About SHEPHERDSTOWN

Shepherdstown, WV Real Estate: Discover Your Perfect Home

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
70
# of Listings
3
Avg # of Bedrooms
$229
Avg. $ / Sq.Ft.
$479,033
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

70 Properties Found. Page 3 of 5.

Amazing location, this charming brick-front home sits on a quiet cul-de-sac in the highly sought-after Maddex Farm community, offering over 4,500 finished square feet of living space. One of the largest homes in the neighborhood, it features a stunning two-story foyer with dual staircases, a sunken living room with vaulted ceilings, and a cozy gas fireplace. The kitchen offers granite countertops, a spacious layout with an eat-in area, a good sized island, and a pantry. Upstairs offers four generously sized bedrooms, each with ample closet space and natural light. The expansive master suite includes tray ceilings, dual walk-in closets and a spacious bathroom with a large soaking tub. The spacious walk-out level basement features a half bathroom, and offers a bright and versatile area for recreation or additional living space. This home has the longest driveway in the neighborhood and a layout that’s both rare and impressive. With its size, and location, this home is a must-see!--Home virtually staged
#WVJF2019704

SHEPHERDSTOWN

85 RAMS COURT

4 Beds

2 Baths

5,138 Sq.Ft.

$520,000

MLS#: WVJF2019704

Historic Downtown Charm Meets Modern Comfort Welcome to 103 E New St — a distinctive historic home in the heart of Shepherdstown, West Virginia, just steps from cafes, shops, Shepherd University, and the C&O Canal National Historical Park. This thoughtfully updated 3-bedroom, 2.5-bath residence blends the warmth of original character with modern conveniences. Step inside to find rich original hardwood floors, tall windows, built-in shelving, and a cozy pellet stove anchoring the living space. The kitchen offers charming custom wood cabinetry, butcher-block counters, and stainless-steel appliances, while the formal dining room showcases period built-ins and timeless trim details. The second level includes 2 additional bedrooms and a primary suite with private balcony, ideal for morning coffee or sunset views. The updated primary full bath features a walk in closet and a large glass-enclosed shower, air jet spa tub, and tile accents — a relaxing retreat. Additional features include in-home laundry, efficient systems, and a standing-seam metal roof. Enjoy the fenced backyard with off-street parking with gardens full of perennials and just a short stroll from everything Shepherdstown offers. Perfect as a primary residence, investment property, or weekend retreat, this home captures the charm of small-town living with convenient access to commuter routes to DC/NOVA.
#WVJF2019016

SHEPHERDSTOWN

103 E NEW STREET

3 Beds

2 Baths

2,244 Sq.Ft.

$520,000

MLS#: WVJF2019016

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

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

Fall Move In! Complete with main level bedroom, and finished basement rec room! Only a stone's throw away from Morgan's Grove Park Entrance. This 2 Story single family home marries features and affordability and comes with everything included. 5 Bedrooms, LVP floors in the main living spaces, included kitchen appliances, granite countertops and Espresso cabinets give the updated look you've always wanted. Located next to Morgan's Grove Park and just down the street from Downtown Shepherdstown!
#WVJF2018712

SHEPHERDSTOWN

92 OPEN GATE LANE

5 Beds

3 Baths

3,129 Sq.Ft.

$499,990

MLS#: WVJF2018712

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

Discover your dream retreat along the banks of the Potomac River in Shepherdstown! This charming 3-bedroom, 2-bathroom contemporary layout offers an exceptional home and a premium riverfront location with panoramic riverfront views. The home is well-suited for entertainment with a cozy living room that adjoins the stylish kitchen and separate dining area, with the added convenience of main-floor laundry and a primary bedroom suite. Both bedrooms on the upper-level provide ample space and enjoy vaulted ceilings with shared access to a large guest bathroom. The 0.21 acre property backs to lush trees with a secluded patio and directly fronts the river providing an ideal combination of privacy and awe-inspiring views. Embrace the outdoor lifestyle with private access to the deep water Potomac River, perfect for boating, fishing, or kayaking. The property features a single-slip private dock for direct access to . Located in a vibrant riverfront community with a boat ramp, this home is a rare find for those seeking a peaceful yet active lifestyle. A new roof was installed in 2023.
#WVJF2016664

SHEPHERDSTOWN

1529 KNOTT ROAD

3 Beds

2 Baths

1,682 Sq.Ft.

$499,900

MLS#: WVJF2016664

New on site 4 days ago
Rare opportunity to find a rancher with beautiful large sunroom addition to take advantage of pretty backyard views! Sunroom has built-in screens, heat and air for year round use! 3 brs on first floor PLUS great room with gas fireplace; pocket doors open to office or any use room AND, breakfast area and room for formal dining space. Full walkout basement has loads of storage and a finished room that this seller used for guest stays. 1/2 bath in basement. Seller has made a purchase but cannot move in until middle of January. A closing this year with a rent back would be perfect for her until then! 1.36 acres in this river community with all homeowners having a common river area that they can access for canoes, small motor boats, kayaks and a picnic area. Home located only minutes from Shepherdstown and all the restaurants, shops and food stores. Shepherd University and easy commuter routes minutes from here also.
#WVJF2020354

SHEPHERDSTOWN

64 WILDFLOWER LANE

3 Beds

2 Baths

3,300 Sq.Ft.

$499,900

MLS#: WVJF2020354

Absolutely gorgeous 4-bedroom, 2.5-bathroom home with approximately 4000 total finished square feet. Located in Shepherdstown WV, and just minutes from Shepherd University, this home has been completely re-done and features a NEW ROOF, new gutters and downspouts, two new HVACS, two brand new hot water heaters, new siding, fresh paint, new hardware and fixtures, all new windows, 2 and a half-remodeled bathrooms, and new LVP flooring throughout. The kitchen has been upgraded with new cabinets, new stainless-steel appliances, and new granite counter tops. There are two family rooms, one of which is massive and can be used as a rec room/ bonus room. Other features include a two-car garage, a front porch, and a rear screened in porch. Don't miss out on this!!!
#WVJF2015504

SHEPHERDSTOWN

71 CARDINAL DRIVE

4 Beds

2 Baths

4,032 Sq.Ft.

$450,000

MLS#: WVJF2015504

Discover a prime investment opportunity in the heart of Shepherdstown, but just outside of town limits! This charming 1920 Colonial-style home boasts 1,530 sq. ft. of excellent condition, featuring stunning wood floors that exude warmth and character. The thoughtfully designed interior includes a combination kitchen/dining area, perfect for entertaining or maximizing rental appeal and an expansive primary bedroom. Indulge in luxury with a jetted soaking tub, enhancing the property's allure for potential tenants seeking comfort and relaxation. The kitchen is equipped with energy-efficient appliances, including a refrigerator, oven/range, and dishwasher. With off-street parking and a spacious driveway, convenience of walking to downtown Shepherdstown, WV and Shepherd University are at your doorstep. A sizeable shed, a former potter's studio, has electric and can be imagined into additional space. This property is furnished, allowing for immediate rental potential. Invest in a home that not only offers aesthetic charm but also promises strong returns in a desirable location. Experience the perfect blend of historic charm and modern living in this delightful investment property or residence, where every detail invites you, or your potential renter, to call it home. PLEASE NOTE: THIS IS AN ACTIVE VACATION RENTAL. ACCESS TO THE PROPERTY IS STRICTLY FOR PERSONS ACCOMPANIED BY THEIR REALTOR, WITH AN APPROVED SHOWING TIME.
#WVJF2020040

SHEPHERDSTOWN

8709 SHEPHERDSTOWN PIKE

2 Beds

2 Baths

1,530 Sq.Ft.

$449,999

MLS#: WVJF2020040

Well maintained 2080sf ranch style home in a cozy spacious setting of 3 acres just minutes from downtown Shepherdstown. Very large decks on both the front and rear of the home. The back deck has a view of a neighboring lake in the fall and winter months, and can be accessed from the living area as well as the primary bedroom. Stunning hardwood floors throughout. Stone two sided fireplace as a centerpiece between the living area and kitchen/dining area. Granite counter tops and plenty of cabinets. Large out building with garage door and side door. Come check out this getaway and maybe be lucky enough to call it HOME!!
#WVJF2020140

SHEPHERDSTOWN

174 BYER LANE

3 Beds

2 Baths

2,080 Sq.Ft.

$449,900

MLS#: WVJF2020140

Elegant Three-Level Townhome 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!
#WVJF2018752

SHEPHERDSTOWN

420 STARKEYS LANDING

4 Beds

2 Baths

2,880 Sq.Ft.

$375,000

MLS#: WVJF2018752

Quick Move In on a Corner Lot! This 2 Story single family home marries features and affordability and comes with everything included. 4 Bedrooms, 2.5 Baths and 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!
#WVJF2018716

SHEPHERDSTOWN

36 OPEN GATE LANE

4 Beds

2 Baths

1,906 Sq.Ft.

$369,990

MLS#: WVJF2018716

Nestled on a generous half-acre lot in historic Shepherdstown, this Split foyer home is a must see within Mecklenburg Heights where there's no HOA, only a road Maintenace Agreement. "Move-in-Ready" and updated inside and out this property works for any type of financing. Inside there are 3 bedrooms, 2 full bathrooms, finished basement and two car garage. Boasting many upgrades like the new roof and gutters, new electric HVAC system (Central Air), new flooring, new cabinets and countertops, new appliances and fixtures, new vanities and toilets, new deck and sliding glass door. The finished basement with full bath provides additional living space that's perfect for a fourth bedroom or a home office and gym. Attached front-entry garage with electric opener and freshly paved driveway are also excellent features that complete this full package. Comes with a washer and Dryer. Don't miss the opportunity to make this affordable Shepherdstown home your own. Just outside of downtown Shepherdstown and the Shepherd University campus area, close to amenities, the Wellness Center, Food Lion, shops and eateries. New main water line from street to home. Motivated seller, will provide Home Warranty for new buyer. Call for your tour today.
#WVJF2017384

SHEPHERDSTOWN

133 MEADOWLARK LANE

3 Beds

2 Baths

1,780 Sq.Ft.

$359,900

MLS#: WVJF2017384

***Motivated Seller, CLOSING COST ASSISTANCE UP TO $10K*** Updated end unit town home located in the Colonial Hills community of Shepherdstown. All three levels are finished and were upgraded with bump outs. Walk in at the lower level to an over-sized family room with full egress window, half bath, laundry room and entry to the attached one car garage. The main level features a dining/sunroom off the eat-in kitchen that leads out to a 16 x 15 deck with views of an open common area. Both rooms have LVP, and the kitchen offers stainless steel appliances, quartz counters, beautifully painted cabinetry, pantry and tile backsplash. The upper level of the home has a primary bedroom with tray and vaulted ceilings, a lovely sitting room and walk-in closet. The ensuite bath features a soaking tub and separate shower.
#WVJF2019340

SHEPHERDSTOWN

302 STARKEYS LANDING

3 Beds

2 Baths

2,308 Sq.Ft.

$350,000

MLS#: WVJF2019340

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