CHARIS REALTY GROUP
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
54
# of Listings
3
Avg # of Bedrooms
$296
Avg. $ / Sq.Ft.
$520,878
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

6 Properties Found. Page 1 of 1.

1585 Gardners Lane: Circa 1850 Farmhouse converted into 6 apartments, 2 cottages and 1 duplex totaling 10 units on 13.2 acres with huge bank barn and fencing/pasture for horses. 100% occupancy, great rental history over past 20 years of ownership. Roughly $11k per month totaling a potential yearly income of $132,910 (2025). Current owner operated and managed these units as short term rentals on month to month leases. Some tenants have remained for many years. One tenant leases a cottage and all the fenced areas and barn for an equestrian business. Tenants pay electric, owner provides Wi-Fi and trash removal. All tenants are on month to month leases. Multiple wells and septic systems. NOTE: 48 HOURS REQUIRED FOR ALL SHOWINGS.
#WVJF2020612

SHEPHERDSTOWN

1585 GARDNERS LANE

6 Beds

6 Baths

3,692 Sq.Ft.

$1,600,000

MLS#: WVJF2020612

1585 Gardners Lane: Circa 1850 Farmhouse converted into 6 apartments, 2 cottages and 1 duplex totaling 10 units on 13.2 acres with huge bank barn and fencing/pasture for horses. 100% occupancy, great rental history over past 20 years of ownership. Roughly $11k per month totaling a potential yearly income of $132,910 (2025). Current owner operated and managed these units as short term rentals on month to month leases. Some tenants have remained for many years. One tenant leases a cottage and all the fenced areas and barn for an equestrian business. Tenants pay electric, owner provides Wi-Fi and trash removal. All tenants are on month to month leases. Multiple wells and septic systems. NOTE: 48 HOURS REQUIRED FOR ALL SHOWINGS.
#WVJF2020542

SHEPHERDSTOWN

1585 GARDNERS LANE

10 Beds

None Baths

3,692 Sq.Ft.

$1,600,000

MLS#: WVJF2020542

Welcome to 414 McMurran Farm Lane, this remarkable property was built for comfort, leisure, and everyday ease. Offering over 5,600 square feet of beautifully designed living space and an adjoining lot (Lot 6) for a total of 18+ acres, this property delivers a rare combination of luxury, functionality, and rural tranquility. From the moment you arrive, the mature tree lined driveway and expansive 365 degree views create a serene and inviting atmosphere. Inside, the home features new wide plank hardwood floors, new crown molding and wainscoting, and custom built-in carpentry throughout, including desks, bookcases, mudroom lockers, and more. The main level includes a generous primary suite and a thoughtful floor plan enhanced by new granite countertops, several new appliances, exceptional storage, and a convenient dog/utility shower in the mudroom. Two gas fireplaces add warmth and charm, while the fully finished walkout basement provides additional space for comfort, by including its own kitchen & full bathroom making it the perfect space for guests, extended family. Outdoor living is a standout with a heated pool, pergola, granite outdoor bar, hardscape patio, and a built-in fire pit, creating a true retreat for relaxation or hosting gatherings. And if you want to enjoy the best of both indoor and outdoors just relax in the sunroom which is temperature controlled and inviting all year round. You and your guest will always have ample parking for your gatherings with the extended driveway and oversized two car garage. So whether you are lounging poolside or relaxing on the front porch watching the sun go down this home has something for everyone to enjoy. For horse lovers, hobby farmers, and anyone seeking a self-sustaining lifestyle, the property includes an impressive equestrian setup and agricultural features. The barn offers two horse stalls and a dedicated tack area, while the fenced paddocks and lighted riding arena provide an excellent environment for training, exercising, and everyday care. Two run-in sheds offer additional shelter, and the high tunnel is ideal for gardening or year-round growing. The acreage and community allow for horses, goats, chickens, and other small livestock, giving you the freedom to maintain the farm or homestead of your dreams. Plus the finished detached garage functions beautifully as a workshop, home gym, or car enthusiast space. Additional highlights include well-maintained HVAC and home systems, abundant closets and storage throughout, new granite counters, and a built-in security and fire alarm system (subscription required for monitoring). If you commute daily then you will really enjoy that it’s located within minutes to a MARC station in a peaceful neighborhood with large rural lots, this exceptional estate offers privacy, versatility, and endless possibilities while remaining close to everyday conveniences. 414 McMurran Farm Lane is more than a home, it's a lifestyle waiting to be experienced.
#WVJF2020498

SHEPHERDSTOWN

414 MCMURRAN FARM LANE

5 Beds

4 Baths

5,641 Sq.Ft.

$1,599,999

MLS#: WVJF2020498

New 19 home Community in Shepherdstown! March 30 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

Beautiful 20.62± acres featuring a large metal barn, an already-dug well (see septic and well records), and a fully fenced property currently used for cattle. Property includes a nice gravel driveway, a cleared house site, and a perfect blend of lovely, wooded areas and open pasture for animals. Located less than 10 minutes from downtown Shepherdstown, this property offers the ideal balance of privacy and convenience. No restrictions and hunting is allowed. Come enjoy nature, peace, and wide-open space just minutes from Shepherdstown. Two lots being sold together: 14.76 AC LOT 1 & MERGER P/O PCL 12.1 EATON SD (14.76 AC, Managed Timber) is located in Berkeley County, and LT 2 NEEDY FARM (5.86 AC) is located in Jefferson County. Buyer shall perform their own due diligence regarding all county-specific requirements, property characteristics, and intended uses. There is an existing grave site on the property. Buyer is responsible for conducting all investigations related to this gravel site and any associated permissions, restrictions, or operations. Seller makes no representations or warranties and shall not be held responsible for any findings related to the gravel site or buyer’s intended use of the property.
#WVJF2020628

SHEPHERDSTOWN

160 OTTER RUN PLACE

None Beds

None Baths

20.62 acres

$1,100,000

MLS#: WVJF2020628

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