CHARIS REALTY GROUP
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SHEPHERDSTOWN

One of the most popular communities provided by Charis Realty Group

SHEPHERDSTOWN

About SHEPHERDSTOWN

Discover Shepherdstown,WV Real Estate 

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 expert on the Charis Realty Group team for personalized guidan ce 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 Group
37
# of Listings
3
Avg # of Bedrooms
$274
Avg. $ / Sq.Ft.
$508,577
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

37 Properties Found. Page 2 of 3.

Welcome to 185 Shepherd Lane, a charming and spacious home just minutes from downtown Shepherdstown, WV. Situated on 2.5076 acres in a peaceful, established neighborhood with large lots, this 4-bedroom, 2.5-bath home offers both comfort and opportunity. A covered front porch welcomes you into the main level, which features a formal living room and dining room (both with beautiful hardwood floors) perfect for hosting, and a cozy family room with a wood-burning fireplace (currently capped) and built-in shelving. There's also a private office or bonus room with natural light and a generously sized mud/laundry room for daily convenience. Upstairs, you'll find all four bedrooms, including a primary suite with its own ensuite bath, while the three additional bedrooms share a full hall bath. The kitchen remains in its original condition—clean and well-kept—providing a great opportunity to update and make it your own. The unfinished basement offers plenty of storage or future expansion possibilities. Recent updates include a new roof in 2025 and a modern HVAC system installed within the past few years. Outside, the in-ground pool is currently not operational, but it remains in place for buyers who wish to restore or reimagine the space. This home offers a rare combination of space, charm, and location—ready for your next chapter in beautiful Shepherdstown.
#WVJF2021232

SHEPHERDSTOWN

185 SHEPHERD LANE

4 Beds

2 Baths

2,176 Sq.Ft.

$550,000

MLS#: WVJF2021232

New on site 4 days ago
Situated on nearly 3 acres just minutes from historic Shepherdstown, this spacious and versatile property offers over 3,500 finished square feet, blending comfort, functionality, and lifestyle in one exceptional offering. The main level features approximately 1,800 square feet of living space with hardwood flooring throughout and a traditional yet open flow. You’ll find a generously sized kitchen with ample workspace, a formal dining room, formal living room, and a warm, inviting family room highlighted by exposed beam accents and a sliding glass door leading directly to the expansive rear deck. Three bedrooms and two full bathrooms complete the main level, providing convenient single-level living. The lower level—fully finished in 2023—adds tremendous value and flexibility. Designed as a complete secondary living space, it includes a full kitchen, dining area, spacious living room, a private bedroom with walk-in closet, a den with wood fireplace, and a full bath. With three sliding glass doors opening to the patio, the space is filled with natural light and offers true walkout access—ideal for an in-law suite, guest quarters, or potential rental opportunity. Outdoor living is equally impressive. Enjoy the large Trex deck, a screened-in porch for relaxing evenings, and a lower-level patio that connects seamlessly to the backyard. The nearly 3-acre setting provides a balance of usable space and privacy, all just a short drive to Shepherdstown’s dining, shopping, and charm. Energy efficiency is a standout feature, with a fully paid-off solar array and EV charging station already in place—offering long-term savings and modern convenience. With its combination of size, flexibility, location, and thoughtful upgrades, this property presents a rare opportunity in one of the area’s most sought-after locations.
#WVJF2023470

SHEPHERDSTOWN

286 FALLING SPRING ROAD

4 Beds

3 Baths

3,502 Sq.Ft.

$535,000

MLS#: WVJF2023470

Welcome home to this charming rancher nestled on 1.8 acres in beautiful Shepherdstown. Enjoy the ease of one-level living with the added potential of a full, walk-out basement—perfect for future expansion or storage. Inside, you’ll find all NEW gorgeous LVP flooring, new carpets in bedrooms, Upgraded kitchen & new appliances, a cozy fireplace area and a spacious primary suite with a large bathroom. The breezeway off the kitchen leads to a convenient two-car garage, combining charm and functionality in one package. This home offers comfort, character, and plenty of room to make it your own!
#WVJF2020426

SHEPHERDSTOWN

104 STONEHOUSE LANE

3 Beds

2 Baths

2,006 Sq.Ft.

$515,000

MLS#: WVJF2020426

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

Private Back to Trees Homesite! Walkout Basement and Finished Rec Room! Sits on nearly a 1/3 acre homesite with great views! Complete with a main level bedroom and full bath, great for guests. This 2 Story single family home marries features and affordability and comes with everything included. 5 Bedrooms a 2nd floor loft, 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!
#WVJF2021592

SHEPHERDSTOWN

126 RIDERWOOD WAY

5 Beds

3 Baths

2,914 Sq.Ft.

$479,990

MLS#: WVJF2021592

Classic Maddex Farm location within walking distance via community trail to Shepherd University and then downtown to shopping and restaurants or the C and O Canal...All within walking/biking distance without hitting a main road! Community features tot lot, common picnic space, and basketball court. Great fenced larger lot with patio for your summer time fun! Inside, the house has been cosmetically overhauled with new flooring, sanded flooring, paint, kitchen renovations, locks, knobs, and hinges, and more! The home shows very well. Please be aware the owners have sensitive jobs and work from the home office. The home office could not be pictured due to type of employment. The office sits right off the front door and features double glass door entry. On showings, if during day, please do not disturb the sellers who may be working in the office, but you are welcome to poke your head in and look around the office space.
#WVJF2023436

SHEPHERDSTOWN

316 MADDEX FARM DRIVE

4 Beds

3 Baths

2,864 Sq.Ft.

$479,900

MLS#: WVJF2023436

Quick Move In w/ walkout basement! Nearly a 1/4 acre homesite and mountain views. 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!
#WVJF2023208

SHEPHERDSTOWN

124 OPEN GATE LANE

5 Beds

3 Baths

2,914 Sq.Ft.

$469,990

MLS#: WVJF2023208

Quick Move In! Back to Trees private quarter acre homesite! Located in Tollhouse Woods, Shepherdstown's newest community located just a mile from the downtown area and university. This property backs to a tree line and sits on a private homesite. This 2 Story single family home marries features and affordability and comes with everything included. 4 Bedrooms, 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!
#WVJF2023210

SHEPHERDSTOWN

42 RIDERWOOD WAY

4 Beds

3 Baths

2,401 Sq.Ft.

$419,990

MLS#: WVJF2023210

Don't miss out on this rare opportunity to own nearly 8 UNRESTRICTED acres in Shepherdstown. Sweeping sunset views make this a perfect location to lay down roots and build your forever home. Build with confidence as major groundwork is already complete. Perc-approved for a 4 bedroom house with well already in place. Experience true flexibility to build your dream home with NO HOA. Although the property itself does not have an HOA, it is situated off of a state maintained road making it accessible but private. Lot is conveniently located close to Route 9, ideal for commuters. If country living with access to modern conveniences is what you seek, then look no further than this picturesque property.
#WVJF2020954

SHEPHERDSTOWN

LOT 3A RIDGE ROAD

None Beds

None Baths

7.85 acres

$392,000

MLS#: WVJF2020954

Located in the Mecklenburg Heights area of Shepherdstown, this 3-bedroom, 2 full bath home offers a functional layout, comfortable living space, and recent updates that make it easy to appreciate from the start. The interior has a clean, refreshed feel with improvements already in place, while still offering a buyer the chance to add personal style over time. Whether you are looking for a primary residence or an investment in a convenient location, 39 Nightingale offers solid value just minutes from downtown Shepherdstown, Shepherd University, and major commuter routes.
#WVJF2022884

SHEPHERDSTOWN

39 NIGHTINGALE LANE

3 Beds

2 Baths

1,656 Sq.Ft.

$329,900

MLS#: WVJF2022884

LOCATION! LOCATION! Great investment property located within walking distance to Historic Shepherdstown & Shepherd University. This total brick bungalow is located on 2.4 partially wood acres. It has a large living room, family room, dining room, kitchen, two (2) bedrooms, full bathroom, large attic which could be converted into a playroom/ office or even a bedroom, full basement w/recreation room and storge room, one car detached garage, storage shed, partially fenced, and black top driveway. House also has enclosed front and back porches, hardwood/tile floors, oil heat and metal roof. This property has incredible potential and needs some TLC. Must be sold in "as is" condition.
#WVJF2022820

SHEPHERDSTOWN

8582 SHEPHERDSTOWN PIKE

2 Beds

1 Baths

2,000 Sq.Ft.

$329,900

MLS#: WVJF2022820

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

Easy one-level living just minutes from Shepherdstown and Shepherd University. This well-maintained home offers a bright, functional layout with a kitchen featuring granite countertops, ample cabinet storage, and generous counter space that opens to the dining area. The home includes three nicely sized bedrooms, laminate flooring, and a convenient laundry closet. Step outside to a spacious rear deck overlooking a private backyard with woods behind the property, providing a peaceful setting for relaxing or entertaining. An oversized two-car garage and plenty of parking add to the home's convenience. Ideally located close to shopping, dining, and everyday amenities while still offering a quiet, comfortable setting.
#WVJF2022462

SHEPHERDSTOWN

510 SPRING WARBLER WAY

3 Beds

1 Baths

1,056 Sq.Ft.

$289,900

MLS#: WVJF2022462

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