Shepherdstown Homes with Pool

Welcome to Shepherdstown, West Virginia, a charming town nestled along the banks of the Potomac River, just a stone's throw from the bustling city of Washington, D.C. As the oldest town in West Virginia, Shepherdstown boasts a rich history, vibrant arts scene, and a close-knit community that makes it a truly special place to call home. With its picturesque streets lined with historic buildings, quaint shops, and delightful eateries, residents enjoy a unique blend of small-town charm and modern conveniences.

For those seeking a home with a touch of luxury, Shepherdstown offers a selection of stunning properties featuring private pools. Imagine spending warm summer days lounging by your pool, hosting barbecues with friends, or enjoying a peaceful evening swim under the stars. These homes not only provide a refreshing escape but also serve as the perfect backdrop for creating lasting memories with family and friends.

Shepherdstown is also known for its outdoor recreational opportunities. With nearby parks, hiking trails, and the scenic Potomac River, residents can indulge in a variety of activities, from kayaking and fishing to hiking and biking. The town is also home to Shepherd University, which enriches the community with cultural events and educational opportunities.

Whether you are looking for a serene retreat or a vibrant community, Shepherdstown offers a delightful lifestyle complemented by the luxury of homes with pools. Dive into the charm of this historic town and discover your dream home today!

Newest Shepherdstown Homes with Pool

$635,000

4 Beds ⋅ 3 Baths

Set on 4.07 acres just minutes from downtown Shepherdstown, this spacious home offers room to spread out, a peaceful setting, and the opportunity to make it your own. A covered front porch leads into a well-designed main level with formal living and dining rooms featuring hardwood floors, a comfortable family room with built-in shelving and a wood-burning fireplace that is currently capped, a private office or bonus room filled with natural light, and a generously sized mudroom and laundry area with wash sink and built-in cabinetry that adds everyday function. The eat-in kitchen is clean and well maintained in its original condition, offering a solid starting point for future updates. All four bedrooms are located upstairs, including a primary suite with its own bath, while three additional bedrooms share a full hall bath. An unfinished basement provides excellent storage and room for expansion over time. Recent improvements include a new roof in 2025 and a newer HVAC system installed within the past few years. Outside, the in-ground pool is not currently operational but remains in place for a buyer who wants to restore it or redesign the outdoor space. With acreage, established neighborhood appeal, and close proximity to Shepherdstown, this property offers a rare combination of space, setting, and long-term potential.

185 Shepherd Ln, Shepherdstown

Listing courtesy of Dandridge Realty Group, LLC. Contact: 3048857645

$535,000

3 Beds ⋅ 4 Baths

Overlooking Cress Creek Golf Club in Shepherdstown, this villa-style duplex offers a setting that feels peaceful, established, and easy to enjoy. Hardwood floors run throughout the main level, where the layout balances comfort and function with a formal dining room, an eat-in kitchen with table space, and a spacious living room centered around a wood burning fireplace with built-in shelving. A large bay window with window seat brings in natural light, and the covered porch extends the living space outdoors with a view of Cress Creek Golf Course, that adds something special to daily life. The upper level includes a primary suite with ensuite bath, a second bedroom, full hall bath, and stacked washer and dryer. On the walkout lower level, a private bedroom suite with full bath, walkthrough closet, and patio access creates flexible space for guests, hobbies, or extended stays. Complete with a 2-car attached garage, this 3 bedroom, 3.5 bath home combines a scenic golf course backdrop with a floor plan designed for comfort, privacy, and ease. All this with easy access to all the restaurants, culture, and community that Shepherdstown, WV has to offer, just an hour outside of Washington, DC.

20 Drennen Ct, Shepherdstown

Listing courtesy of Dandridge Realty Group, LLC. Contact: 3048857645

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