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

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
69
# of Listings
3
Avg # of Bedrooms
$228
Avg. $ / Sq.Ft.
$467,870
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

69 Properties Found. Page 5 of 5.

Prime real estate offering high visibility and robust traffic count, making it the perfect location for your business. Situated on a corner lot with dual access from Martinsburg Pike and Old Martinsburg Rd, this property offers a surplus of parking spaces. Ideal for medical or professional offices. Tenants are responsible for any improvements required to create their ideal workspace. Featuring 2,000 square feet of space, including five private offices or rooms, a generous 16x19 reception area, two separate restrooms or powder rooms, make it an excellent choice for a variety of businesses. The landlord is open to five year lease agreement, ensuring stability for your business.
#WVJF2016144

SHEPHERDSTOWN

7595 MARTINSBURG PIKE D

None Beds

None Baths

N/A

$3,350

MLS#: WVJF2016144

Absolutely immaculate Victoria Model in the highly desired Maddex Farm community. Like new carpet through out, walls and ceilings were just freshly painted. Wood floors in foyer, vinyl in kitchens and baths, granite counters, new stainless appliances, partially finished walk-out basement with built in book cases, and half bath, Master suite with whirlpool tub/dual vanity/walk-in closet. Unfinished basement space for storage, two car garage, fenced in rear yard, and a large rear deck for entertaining and cooking out. No pets please. $40 application fee, criminal background and credit checks apply. $2,650/mo. & $2,650 security. Ready for your immediate occupancy.
#WVJF2018304

SHEPHERDSTOWN

72 MADDEX FARM DRIVE

4 Beds

2 Baths

3,302 Sq.Ft.

$2,500

MLS#: WVJF2018304

Presenting another quality 4 BR, 2 1/2 bath rental home in the highly desired Maddex Farm community. Hardwood floors throughout most of first level, new stainless appliances, gas fireplace in the large living room, breakfast room off kitchen, master suite with tray ceiling, walk-in closets, and deluxe bath with soaking tub and shower. Nice rear deck with partially fenced in back yard. Full, unfinished, walk-out basement with tons of storage. $2,500/mo. & $2,500 security. NOTE: There is a no pet policy for this property. Owner requires average credit score to be over 650. 24 hours notice required prior to showing.
#WVJF2019650

SHEPHERDSTOWN

215 MADDEX SQUARE DRIVE

4 Beds

2 Baths

3,000 Sq.Ft.

$2,500

MLS#: WVJF2019650

Maddex neighborhood of Shepherdstown, this home is a spacious, light filled open design, two story 4 bdrm, 2 1/2 bath, double car attached garage. The location, within two min. drive of historic Shepherdstown, a short walk to the University, cultural events and surrounding recreation areas galore. This sought after location, plenty of large high windows all around, mature trees, landscaping and a privately fenced spacious backyard in a quiet neighborhood is hard to find. The front entrance features a large gracious entry foyer, two story high ceiling, w/ a view to the upstairs hallway overlook, wood flooring. On the left of the foyer, through french doors, you’ll find the Library/ofc room with new Gunstock Oak flooring, and floor to ceiling windows. To the right of the entry foyer the home features a living room with floor to ceiling windows, and separate formal dining room with lots of light. Walking through the front hall/entry foyer, you’ll appreciate the ample coat closet, 1/2 bath, separate Large laundry room w/ tile flooring and convenient entrance from attached garage. Spacious kitchen features stainless appliances, large center island w range top, a double sink, built in double wall ovens, microwave and recessed lighting, open to the casual eating area and large family room, featuring a gas fireplace and mantel, high windows all around, a ceiling fan. From the casual family eating area you will enjoy going out to the wide entertainment deck along the entire back of the home, with stairs down to the landscaped backyard. Wood fenced back yard w beautiful mature trees. A full bath and linen closet serve three light filled bedrooms, each w closets . A separate double door entrance off the hall leads to the private primary bedroom, w/ an extra sitting room area, large mirrored closet doors, vaulted ceiling and fan. Master bathroom features a walk in shower (will be renovated prior to being leased) and soaking tub, 2 separate vanities, grey wood laminate flooring, lots of storage space, and full wall mirror. The toilet is in a separately enclosed area.
#WVJF2020190

SHEPHERDSTOWN

24 BUTCHER COURT

4 Beds

2 Baths

3,241 Sq.Ft.

$2,400

MLS#: WVJF2020190

3 BR, 2 1/2 bath interior townhouse in Colonial Hills Subdivision close to town and across from Morgan's Grove Park. Tall ceilings, open floor plan, clean and ready to occupy. All electric heat and air, master bedroom suite with walk in closet, breakfast room off kitchen, carpet through out LR, FR and BR, vinyl in kitchen and baths, separate laundry in lower level, and 1 car garage. Potential for 4th bedroom on main level. NOTE: This rental has a successful history of being a strictly pet free property. No pets will be allowed so please do not inquire about such. Owners request credit scores of 650 or above to be within consideration.
#WVJF2020344

SHEPHERDSTOWN

115 SWEARINGEN WAY

3 Beds

2 Baths

1,600 Sq.Ft.

$1,900

MLS#: WVJF2020344

Modern professional office suite in Shepherdstown now available for lease. Ample parking. Good traffic and visibility off Rt 45. Centrally located to Shepherd University, downtown historic district, Maddex Square Mall. 1,100 Square feet includes front of office space in its entirety. 4 offices, 1 storage room, 1 bathroom, 1 kitchenette area. Shelving and countertops optional. Staff parking in back, 6+ client parking spaces.
#WVJF2019550

SHEPHERDSTOWN

51 MADDEX DRIVE

None Beds

None Baths

N/A

$1,700

MLS#: WVJF2019550

Ground level apartment with separate entrance in the heart of Shepherdstown, WV. Walk to Shepherd University or many other downtown destinations. This unit features high ceilings and lots of charm. One bedroom, one bath with eat-in kitchen and separate living room. Key pad entry at main entrance.
#WVJF2020208

SHEPHERDSTOWN

114 S PRINCESS STREET 1

1 Beds

1 Baths

600 Sq.Ft.

$1,050

MLS#: WVJF2020208

Second floor, one bedroom, one bath apartment with galley kitchen and separate living room. Walk to Shepherd University or many other downtown destinations. Building main entrance secured with key pad entry.
#WVJF2020212

SHEPHERDSTOWN

114 S PRINCESS STREET 3

1 Beds

1 Baths

600 Sq.Ft.

$950

MLS#: WVJF2020212

Cute third floor, one bedroom, one bath apartment with separate living room. Walk to Shepherd University or many other downtown destinations. Building main entrance secured with key pad entry.
#WVJF2020214

SHEPHERDSTOWN

114 S PRINCESS STREET 5

1 Beds

1 Baths

500 Sq.Ft.

$900

MLS#: WVJF2020214

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