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
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

3 Properties Found. Page 1 of 1.

Welcome to The Thomas Shepherd Inn, a celebrated gem in the heart of Shepherdstown — West Virginia’s oldest town and one of its most beloved destinations. Voted WV’s “Best Bed and Breakfast” in 2023, this turnkey property offers a rare opportunity to own a thriving inn with reservations booked well into next year. Whether you continue its legacy as a B&B or reimagine it as a private residence, the possibilities are as rich as the town’s historic roots. Boasting 7 bedrooms and 7.5 baths, including four recently renovated bathrooms, the Inn blends timeless charm with thoughtful updates. Acoustic windows, (2) commercial-grade washers and dryers, and private rear parking enhance comfort and convenience. The property is fully equipped for seamless operation and ready for its next chapter. Located on iconic German Street, the Inn offers unbeatable walkability to Shepherd University, local shops, eateries, cultural events, and the C&O Canal trail. Guests and owners alike enjoy the rhythm of small-town life — from porch chats to art festivals — all within steps of home.
#WVJF2019654

SHEPHERDSTOWN

300 W GERMAN STREET

7 Beds

8 Baths

4,972 Sq.Ft.

$1,249,000

MLS#: WVJF2019654

New 19 home Community in Shepherdstown! Late March 2026 delivery on this New Cape Cod Home on 2 +/- acres! As you approach the home, a paved driveway creates a welcoming sense of arrival. The Cape Cod's classic gabled roof, symmetrical façade, and dormer windows exude traditional elegance, while contemporary finishes lend a fresh and inviting aesthetic. Step inside to discover a thoughtfully designed floor plan, where natural light pours through large windows, highlighting the beauty of the surrounding forest. The main level features an open-concept living space, perfect for both cozy family evenings and entertaining guests. A gourmet kitchen serves as the heart of the home, complete with sleek quartz countertops, custom cabinetry, stainless steel appliances, butlers pantry and a spacious island. Adjacent to the kitchen, a formal dining area and an inviting family room with a fireplace offer warmth and charm. The primary suite, located on the first floor, is a sanctuary of comfort, boasting a spa-inspired en-suite bathroom with a soaking tub, walk-in shower, and dual vanity. A generous walk-in closet completes the space, ensuring convenience and luxury. Upstairs, an additional bedroom/bonus room provides ample space for family or guests, with full bath convenience. This versatile room offers flexibility, whether you envision a home office, playroom, or media space. Outside, the expansive property provides endless opportunities to connect with nature. Explore through the partially wooded acreage, create outdoor living areas, or simply enjoy the serenity of your private retreat. Despite its secluded feel with amazing mountain views, this home is conveniently located within a short drive of local amenities, schools, and shopping. This Cape Cod masterpiece blends the best of traditional craftsmanship, modern amenities, and natural beauty. Whether you’re searching for a forever home or a weekend getaway, this property offers a rare chance to enjoy the best of both worlds—elegant living surrounded by the tranquility of 2+/- acres. Garage has plenty of room and storage. 816 square feet insulated, painted trimmed and finished floor. This house will please the most discerning taste. Don’t miss the opportunity to make this extraordinary home yours!! Pictures are from a previously constructed home.
#WVJF2019748

SHEPHERDSTOWN

17 MISTLETOE LANE

5 Beds

4 Baths

6,394 Sq.Ft.

$1,199,999

MLS#: WVJF2019748

A Rare Historic Estate with Over 100 Acres in Scenic Jefferson County, WV Truly a one-of-a-kind gem with deep roots in history! Originally established in 1804, this remarkable property spans over 100 acres of rolling pastures and active Christmas tree fields, and is protected under the Jefferson County Farm Land Protection Easement. Managed by Dan and Bryan Holler, the Christmas tree farm adds charm and functionality to this working agricultural estate. A local farmer is maintaining the pastures. Tucked away on peaceful country roads, the journey to the farm is part of the magic. Once you arrive and make your way down the long driveway, you're greeted by breathtaking views of tree-covered hills, open fields, and distant mountains—a perfect escape from the hustle and bustle of city life. The 4-bedroom, 2-bath farmhouse offers a spacious family room and timeless character. Additional structures include a well-built milking/bank barn, a run-in shed, a well house, a spacious workshop/garage—ideal for storage, agricultural use, or even potential event space. You'll also find historical artifacts throughout the property that speak to its storied past. Whether you're looking to farm, invest, or simply enjoy the land, this property offers endless possibilities. The location strikes the perfect balance between privacy and convenience, situated just 70 miles from Washington, D.C., and minutes from the MARC commuter train. With majestic views, rich agricultural potential, and a 180-day growing season, Jefferson County is a haven for both full-time and part-time farmers. Close proximity to local markets makes this area ideal for livestock, crops, winery, microbrewery, equestrian, or horticultural operations. Leasing farmland to existing operators is also a viable option. This is a rare opportunity to own a legacy property in one of West Virginia's most scenic and fertile regions. Don’t miss the virtual tour, video, and documents available with this listing! The agent is required to attend all showings. Please schedule 24 hours in advance.
#WVJF2019628

SHEPHERDSTOWN

364 KNOTT ROAD

4 Beds

2 Baths

3,148 Sq.Ft.

$1,199,000

MLS#: WVJF2019628

Buyers resources
7 Reasons to Work with a Realtor
7 Principles For Home Buying Success
Getting a Mortgage To Buy a Home
Home Hazards Awareness
Key Items For Home Inspection
Questions When Buying a Condo
Questions When Choosing a Realtor
Sellers resources
8 reasons to work with a realtor
Calculating Capital Gains
Checklist for Better Showing
Cleaning Home For Sale
Improving Odds Of an Offer
Preparing Home for photoshoot
Selling Your Home for More $$

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