Shepherdstown Homes under $500,000

Shepherdstown Homes under $500,000

Nestled in the heart of Jefferson County, West Virginia, Shepherdstown is a charming small town that seamlessly blends rich history with vibrant community spirit. Established in 1734, this picturesque locale is renowned for its quaint streets, historic architecture, and stunning views of the Potomac River. With a population of just over 1,700 residents, Shepherdstown offers a tight-knit community feel, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle.

One of the town’s standout features is its commitment to the arts and education, highlighted by the presence of Shepherd University. This institution infuses the area with youthful energy and a variety of cultural events, from art exhibitions to live performances. The town also boasts an array of charming shops, delightful cafes, and fine dining options, ensuring that residents and visitors alike can indulge in local flavors and unique finds.

For those looking to call Shepherdstown home, the real estate market offers an array of options, with many beautiful homes available for under $500,000. From historic properties that echo the town’s storied past to modern residences that cater to today’s lifestyle, there’s something for everyone. Whether you desire a cozy cottage or a spacious family home, Shepherdstown's diverse housing options make it an attractive choice for buyers at any stage of life.

Experience the allure of Shepherdstown, where history meets modern living in a breathtaking setting. Your dream home awaits in this enchanting town!

Newest Shepherdstown Homes under $500,000

43 Bon Aire Dr, Shepherdstown
$449,900
4 Beds ⋅ 3 Baths
Historic Shepherdstown Villa – Spacious, Flexible Living! Located in historic Shepherdstown, WV, this well-appointed villa offers 4 bedrooms, 3 full bathrooms, and plenty of space for comfortable living and entertaining. The versatile floor plan features 2 bedrooms on the main level and 2 additional bedrooms on the lower level, making it ideal for guests, a home office, or extended living arrangements. The main level offers an eat-in kitchen, formal dining room, and spacious living room, along with a primary bedroom featuring a private bath and walk-in closet. Step outside to enjoy the rear deck, perfect for relaxing or entertaining. The lower level provides additional living space with a recreation room, two bedrooms, and a full bathroom, large laundry and separate utility room for storage plus convenient access to the rear patio. Situated on a corner lot, the property also features a 2-car garage and paved driveway. New roof and gutters coming in October, 2026! A great opportunity to enjoy the comfort and convenience of villa living in the charming and historic Shepherdstown area!

43 Bon Aire Dr, Shepherdstown

Listing courtesy of RE/MAX Real Estate Group. Contact:

32 Shaw Pl, Shepherdstown
$499,000
3 Beds ⋅ 4 Baths
Welcome to Shaw Pl! Nestled in the charming Maddex Farm community, this stunning Colonial-style home offers a perfect blend of comfort and elegance. Built in 2011, this meticulously maintained residence boasts 2,692 square feet of thoughtfully designed living space, ideal for both relaxation and entertaining. Step inside to discover a warm and inviting atmosphere, highlighted by beautiful brick construction that exudes timeless appeal. With three spacious bedrooms and three and a half bathrooms, there's ample room for everyone to enjoy their own private retreat. The oversized attached garage provides convenient access and plenty of storage for your vehicles and outdoor gear. The well-appointed kitchen is ready for your culinary adventures, and enjoy a light filled bonus space off the kitchen with ample table space and a view of the private fully fenced rear yard. A perfect spot to unwind after a long day. The lower level is finished and includes another full bathroom, and plenty of storage! Outside, the generous 0.37-acre lot at the end of a cul-de-sac offers endless possibilities for outdoor activities, or simply enjoying the fresh air. The peaceful surroundings of Maddex Farm create a serene backdrop for your new lifestyle, while still being conveniently located near local amenities. This home is not just a place to live; it's a place to create lasting memories. Experience the perfect blend of comfort, style, and community in this beautiful residence. Don't miss your chance to make it your own!

32 Shaw Pl, Shepherdstown

Listing courtesy of Keller Williams Realty Centre. Contact:

260 Fernbank Dr, Shepherdstown
$450,000
3 Beds ⋅ 2 Baths
Nestled in the charming Fernbank community, this delightful twin home offers a perfect blend of comfort and convenience. Built in 1999, this villa-style residence features 3 spacious bedrooms and 2 full bathrooms, providing ample space for relaxation and gatherings. The fully finished daylight basement adds versatility, perfect for a home office or entertainment area. Enjoy serene views of the nearby golf course from your backyard, creating a peaceful retreat right at home. The 0.38-acre lot provides plenty of outdoor space for gardening or leisure activities. With an attached garage and driveway parking, convenience is at your fingertips. Fernbank is known for its welcoming atmosphere, with nearby parks and recreational facilities that encourage an active lifestyle. Local schools are highly regarded, ensuring quality education for all. The community also benefits from efficient public services, including snow removal, making winter months hassle-free. Experience the warmth of this neighborhood and make this lovely property your new home!

260 Fernbank Dr, Shepherdstown

Listing courtesy of Coldwell Banker Premier. Contact:

7 Old Prospect Ave, Shepherdstown
$460,000
4 Beds ⋅ 2 Baths
Multi-unit Property! Unique opportunity in the heart of Shepherdstown! This versatile property features two separate living spaces under one roof, each with its own kitchen, making it ideal for multi-generational living, in-law suite, rental income potential, or owner-occupancy with additional living quarters. Keep units separate or combine them back together to create a larger single residence. Enjoy private rear porches overlooking the backyard, providing inviting outdoor space for relaxing or entertaining. Conveniently located near downtown Shepherdstown, Shepherd University, shopping, dining, and local amenities.

7 Old Prospect Ave, Shepherdstown

Listing courtesy of Path Realty. Contact:

17 Old Prospect Ave, Shepherdstown
$370,000
3 Beds ⋅ 1 Baths
Charming home just outside of town limits. Walking distance to downtown Shepherdstown with convenient access to local restaurants, shops, parks, and the University. This residence features a welcoming atmosphere with spacious living areas, abundant natural light, and lots of character. Enjoy outdoor living with a beautiful back yard and mature landscaping. Close to commuter routes while maintaining the charm and tranquility of one of West Virginia's most sought-after historic communities.

17 Old Prospect Ave, Shepherdstown

Listing courtesy of Path Realty. Contact:

7341 Martinsburg Pike, Shepherdstown
$162,900
3 Beds ⋅ 1 Baths
3 Bedroom 1 Bath Manufactured home conveniently located in Shepherdstown. Convenient to shops, restaurants, college, and recreational C&O Canal & River. "Virtually staged/AI-enhanced photos illustrate potential improvements; see original photos for current condition" Buyers should exercise due diligence to verify all information & property details.

7341 Martinsburg Pike, Shepherdstown

Listing courtesy of Prime Location Realty, LLC. Contact:

35 Oatfield Ct, Shepherdstown
$349,900
3 Beds ⋅ 3 Baths
Discover the charm of this beautifully renovated Cape Cod home nestled in the desirable Maddex Farm community. With a major renovation completed in 2026, this residence boasts an excellent condition and upgrades throughout. The upgraded countertops and luxury vinyl plank flooring add a touch of elegance, while the breakfast area invites casual dining. This home features three comfortable bedrooms, including a main level primary en-suite with a walk-in closet, ensuring ample storage. Outside, the lot is situated on a peaceful cul-de-sac, providing a safe environment for outdoor activities. Across the street is community common space with a wooded stream area and just across from the intersection of Oatfield and Hensell is the community playground and picnic area. The community offers fantastic amenities, including basketball courts, playgrounds, and a paved walking path to the Shepherd University grounds at the Wellness Center. Using this path, literally 200 yards from your home, you can access safe travel to Shepherd University, downtown Shepherdstown, and the C and O Canal, all within walking or biking distance. With an attached garage and paved driveway, parking is a breeze.

35 Oatfield Ct, Shepherdstown

Listing courtesy of Samson Properties. Contact:

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