Shepherdstown Homes with Pool

Welcome to Shepherdstown, West Virginia—a charming town that seamlessly blends rich history with modern living. Nestled in Jefferson County, Shepherdstown is one of the oldest towns in West Virginia, boasting a vibrant arts scene, picturesque landscapes, and a tight-knit community. With its quaint streets lined with historic buildings, delightful shops, and cozy cafes, this town is a haven for those who appreciate a slower pace of life.

One of the most appealing aspects of Shepherdstown is its proximity to the Potomac River, offering residents ample opportunities for outdoor activities, including kayaking, hiking, and biking. The town is also home to Shepherd University, which adds a youthful energy and a variety of cultural events throughout the year. Whether you're wandering through the historic district or enjoying a meal at one of the local eateries, you’ll find that Shepherdstown is full of charm and character.

For those looking to make Shepherdstown their home, you'll be pleased to discover a selection of stunning properties that come with one of the most sought-after amenities—private pools. Imagine spending warm summer days lounging by your own pool, hosting barbecues with friends, or simply unwinding in your personal oasis. Homes with pools in this picturesque town not only provide a luxurious lifestyle but also enhance the overall appeal of living in such a vibrant community.

Explore the homes available in Shepherdstown today, and find your perfect sanctuary where history meets modern comfort, all with the added bonus of a refreshing pool at your doorstep.

Newest Shepherdstown Homes with Pool

$635,000

4 Beds ⋅ 3 Baths ⋅ WVJF2024712 MLS

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

$535,000

3 Beds ⋅ 4 Baths ⋅ WVJF2023750 MLS

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

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