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
40
# of Listings
3
Avg # of Bedrooms
$283
Avg. $ / Sq.Ft.
$477,081
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

40 Properties Found. Page 3 of 3.

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.

$299,000

MLS#: WVJF2022462

Shepherdstown on a Half Acre and NO HOA! Close to downtown Shepherdstown and Shepherd University for UNDER 300K!! This cozy home features 3 bedrooms, 2.5 baths, fireplace and fully fenced back and Side fenced area. Large separate dog kennel area that is perfect for dog owners! Is also a good college student rental option. New stainless-steel dishwasher, riding lawn mower and outside Shed included. Seller is motivated, just lowered price! Appraised for $310,000 FHA recently and has been dropped to $269,900.00 to allow for a $14,000 foundation/structural issue to be fixed. We have the reports and estimate to repair uploaded in Documents....Bring all offers!
#WVJF2020970

SHEPHERDSTOWN

32 SCOTT DRIVE

3 Beds

2 Baths

1,320 Sq.Ft.

$269,900

MLS#: WVJF2020970

Shepherds Cove Potomac River Waterfront Community, Shepherdstown WV Lot 20 is an exceptional opportunity READY TO BUILD, beautiful wooded lot with well installed, lot has been cleared for house construction, community septic. Peaceful, tranquil setting. Shepherd Cove is a small , resort-like community of 19 lots with only 3 remaining. These large private lots have marina privileges, and private river access. Enjoy the beauty of nature in the wooded setting. Hiking trails and Biking paths boating, fishing, swimming, kayak and canoe. Marina with individual dock space may be available. Cress Creek Country club/golf club nearby. Private access to 12 navigable miles of the beautiful Potomac River. Community Pavilion overlooking the Potomac with outdoor kitchen, picnic gazebo, barbecue and fire pit. Bocce court and putting green. Away from it all yet convenient location. Minutes to downtown Shepherdstown, Shepherd University, boutique shops, Great restaurants. An area of interesting folks, and cultural activities. Minutes to Marc commuter train to DC, 50 miles to Washington DC and Baltimore. Brochure provided in attached documents. For the person who has longed for a water oriented country escape that is both private and convenient, with woods and paths for nature walks, where deer, foxes, wild turkeys and eagles are abundant; this is the proverbial once in a lifetime opportunity. The opportunities for kayaking, fishing, hiking, boating and communing with nature are endless. Available Lots: Lot #2, 3.790 Acres, $195,000, Lot #5 3.98 Acres, $183,000 Lot #20, 4.356 Acres $209,,000 READY TO BUILD, Well installed, lot cleared,, Lot #9 5.3 acres LAST RIVER FRONT LOT Located on a bluff overlooking the Potomac BEAUTIFUL WOODED LOT, BEAUTIFUL BEAUTIFUL VIEWS up and down river $562,000,00. Motivated seller
#WVBE2033938

SHEPHERDSTOWN

Lot #20 SHEPHERDS COVE SWIFT RIVER WAY

None Beds

None Baths

4.36 acres

$209,000

MLS#: WVBE2033938

Shepherds Cove Potomac River Waterfront Community, Shepherdstown WV Home Sites in a small , resort-like community. Hurry the last 4 lots available in a community of 19 lots. Large private lots with marina privileges,. Enjoy the beauty of nature in the wooded setting. Hiking trails and Biking paths boating, fishing, swimming, kayak and canoe. Marina with individual dock space may be available , Private access to 12 navigable miles of the beautiful Potomac River. Community Pavilion overlooking the Potomac with outdoor kitchen, picnic gazebo, barbecue and fire pit. Bocce court and putting green. Away from it all yet convenient location. Minutes to downtown Shepherdstown, Shepherd University, boutique shops, Great restaurants. An area of interesting folks, and cultural activities. Minutes to Marc commuter train to DC, 50 miles to Washington DC and Baltimore. Brochure provided in attached documents. For the person who has longed for a water oriented country escape that is both private and convenient, with woods and paths for nature walks, where deer, foxes, wild turkeys and eagles are abundant; this is the proverbial once in a lifetime opportunity. The opportunities for kayaking, fishing, hiking, boating and communing with nature are endless. Available Lots: Lot #2 3.790 Acres, $195,000, Lot #5 3.98 Acres, $183,000, LOT 20, $209, 000 READY TO BUILD, well installed, lot cleared for construction. Lot 9 5.3 ACRES $562,000.00 LAST WATERFRONT LOT Sits on bluff overlook the Potomac. BEAUTIFUL BEAUTIFUL VIEWS UP AND DOWN THE RIVER. Motivated seller
#WVBE2013868

SHEPHERDSTOWN

Lot #5 SHEPHERDS COVE SWIFT RIVER WAY

None Beds

None Baths

3.39 acres

$183,000

MLS#: WVBE2013868

New on site today
Build your dream home on this one of kind opportunity. Property features 0.75 Acres with public water and sewer available. One of the last remaining lots located in the North Hills section of The Club at Cress Creek which is the Eastern Panhandles only Private Country Club that features Golf, Tennis, Swimming, and Dining.
#WVJF2023204

SHEPHERDSTOWN

Lot #14 (North Hills) BRIAR MOUNTAIN DRIVE

None Beds

None Baths

0.74 acres

$179,900

MLS#: WVJF2023204

Tucked within one of the Eastern Panhandle’s most sought-after communities, Lot 107 on Reachcliff Drive presents a once-in-a-generation opportunity to build your custom home in Fernbank—known for its natural beauty, welcoming neighbors, and golf course setting. This lot provides 89' of frontage along the 5th fairway. Positioned at the highest elevation in the neighborhood, this wooded lot offers spectacular views of the Cress Creek Golf Course and protected countryside beyond. Located on a quiet cul-de-sac, Reachcliff Drive is prized for its peaceful atmosphere and refined homes valued up to $1M. With public water, sewer, and cable available, and a topography that supports a sunny walkout basement, this lot is ready for your architect and builder. The generous depth allows for privacy while still enjoying sweeping views and golf course access. Just minutes from the Potomac River, downtown Shepherdstown, and MARC commuter rail to DC, Fernbank offers an ideal blend of tranquility and convenience. Don’t miss your chance to own one of the premier homesites in the region.
#WVJF2019398

SHEPHERDSTOWN

REACHCLIFF DRIVE

None Beds

None Baths

0.66 acres

$179,500

MLS#: WVJF2019398

Lot 9, Briar Mountain Drive, North Hills at Cress Creek is one of the last remaining lots available in the sought after Shepherdstown's Premier 18 hole private golf course community. The cul-de-sac lot with access to water and sewer is waiting for your custom home to be built. This beautiful lot which borders a working farm preserved by a conservation easement offers peaceful privacy. Whether you play golf or just want an awe-inspiring neighborhood, you'll find a LOT to love when you choose to live in a golf course community. Cress Creek also offers flexible social, golf, tennis and pool membership options. North Hills at Cress Creek is located in close proximity to the Historic Downtown Shepherdstown where you will find unique and specialty shops along with variety of restaurants to suit your taste and budget. Whatever you enjoy, you can find in Shepherdstown and surrounding areas!
#WVJF2021242

SHEPHERDSTOWN

BRIAR MOUNTAIN DRIVE LOT 9

None Beds

None Baths

0.75 acres

$140,000

MLS#: WVJF2021242

This 2.35-acre BUILDABLE parcel ("Lot 3") on Morgan Grove Road is located beside house #583. Lawn, trees and paved DRIVEWAY access are already in place. Not part of an HOA, the lot is UNRESTRICTED. A detailed SURVEY shows the boundary lines and septic reserve area. A septic PERC test is on file. Easements are in place for the electric company, and house #583 has a right-of-way along the driveway. The LOCATION is superb! This rural setting is conveniently close to historic Shepherdstown for dining, events and shopping; minutes from Duffields MARC commuter train station and Morgan Grove Park; and about an hour from Dulles Airport.
#WVJF2022986

SHEPHERDSTOWN

MORGAN GROVE ROAD 2.35 ACRES

None Beds

None Baths

2.35 acres

$120,000

MLS#: WVJF2022986

Residential building lot opportunity here! Corner lot to Maddex Drive, Martinsburg Pike and Hensel Drive. Directly across from the Shepherdstown Fire Department and Maddex Professional Court. .4382 acre lot. Can not operate any commercial establishment on the premises herein conveyed where gasoline or gasoline products or food or beverages are sold at either wholesale or retail, and that they will not permit any of their assign or leases to use the premises for the forenamed purposes. Due diligence required by purchaser including but not limited to commercial/multi-family potential, building permits, impact fees and city water/sewer hook up availability and locations. This lot is not in the Maddex Farm HOA.
#WVJF2021582

SHEPHERDSTOWN

MADDEX DRIVE

None Beds

None Baths

0.43 acres

$99,900

MLS#: WVJF2021582

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Buyers resources
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Calculating Capital Gains
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