luxury property for sale Middleway, United States

Welcome to Shotwell Farm, a 172-acre equestrian estate and recognized Jefferson County landmark. A tree-lined drive leads to a Southern Living style main home with a detached garage and 2-bedroom apartment. A circular drive serves the residence, while a separate entrance directs visitors to the equestrian facilities. The main barn spans 37,857 square feet and features a center-stall layout, generator, reception area, two offices, laundry, and three staff apartments (one on the first floor, two above). Beyond reception are 29 stalls, a wash stall, and a 80' x 300' indoor arena at the core of the barn. Nearby, a 12,000-square-foot building includes a dedicated breeding area and a 2,520-square-foot maintenance shop with 200-amp service and water. An additional 39 stalls bring the total to 68. Two 6,000-square-foot structures at the rear provide hay and equipment storage; the hay barn includes a 16' x 100' lean-to. Pastures are enclosed by 18,000 linear feet of four-rail blackboard fencing and 7,500 feet of top-rail fencing with diamond wire. The farm is well-equipped with run-in sheds, ample storage, and 29 automatic waterers. Also on the property is a 1,200-square-foot split-level manager’s home with 3 bedrooms, 2 baths and an attached 2-car garage. Beautiful rolling pastured, convenient to both Charles Town racetrack and Virginia.

Price reduced, with motivated sellers! Welcome to 222 Cavalry Drive — a beautifully maintained brick-front colonial offering timeless style, functional living, and exceptional versatility throughout. Situated on a 0.28-acre lot in the established Pioneer Heights community, this home features 5 Bedrooms, 3.5 baths 2 car garage and over 2,800 Sqft of living space. Step inside to gleaming hardwood floors across the main level, which features formal living and dining spaces, a cozy family room with a gas fireplace, and an inviting kitchen with a breakfast nook. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite with a walk-in closet and a private bath complete with a double vanity and soaking tub. The 3rd floor has another full bath to serve the additional bedrooms, all rooms are nicely sized and complete with plush carpeting. Head downstairs to a fifth bedroom, a recreation room/den, a full bathroom, and a workshop with a walkin closet, which adds incredible flexibility and additional storage space. Outside you'll enjoy your spacious covered porch, overlooking the fully fenced, lush backyard and expansive rear patio— the perfect setting for entertaining, relaxing, or enjoying quiet evenings at home. Conveniently located on Winchester’s east side, just minutes from your favorite shopping and dining + easy access to commuter routes, and the historic Winchester walking-mall! — This one has it all! Schedule your private tour today! *Open House 07/25/2026 11am-2pm**

Featured in the New York Times, the Parran House is rich in history, dating back to circa 1792 and showcases a seamless blend of early American character and thoughtfully executed modern updates. Nestled in Shepherdstown, the state’s oldest and most charming small town, the property beautifully captures its colonial heritage while also reflecting the rich Civil War history that shaped the region. This extraordinary property offers a rare fusion of historic charm and modern versatility, featuring an original main residence alongside two fully renovated private apartments, an ideal setup for both living and reliable income generation. Across the entire property, five bedrooms, four full bathrooms, and three fully equipped kitchens provide exceptional flexibility for a variety of residential and rental configurations. Offered with flexibility, the home may be conveyed largely turnkey with an acceptable offer, presenting a rare opportunity for a seamless transition. Perfectly positioned in the heart of town, it offers effortless access to acclaimed restaurants, curated boutiques, and the vibrant campus of Shepherd University. This highly desirable location not only enhances everyday convenience but also supports strong, consistent demand for long-term rentals, making it as compelling an investment as it is a home. Inside, the home’s historic character is exquisitely preserved, with original heart pine floors, windows, and detailed millwork creating a warm and authentic backdrop. Multiple fireplaces add charm and timeless elegance throughout. Soaring ceilings and a gracious, sun-filled foyer set an inviting tone, while the living and dining rooms sit on either side. The main level is completed by a well-appointed kitchen and a full bath. Upstairs, the second floor features three generously sized bedrooms along with the added convenience of a dedicated laundry area. Above it all, a spacious attic provides excellent storage or presents an exciting opportunity for expansion or customization. Along with the main residence are two self-contained one-bedroom apartments, each featuring a full bath, a fully appointed kitchen, and an open-concept living and dining area. Each unit, including the main home, offers its own private entrance, separate utilities, and individual addresses, ensuring complete privacy and independence. The apartments showcase exposed and restored stone and brick walls and fireplaces that add authentic historic character, while the upper unit is distinguished by a striking beamed ceiling. Every detail has been updated for both comfort and style: hardwood floors, modern plumbing, separate HVAC systems, and individual water heaters ensure convenience and efficiency. Contemporary kitchens, equipped with stainless steel appliances and designer finishes, create inviting spaces for cooking and entertaining, while carefully positioned lighting enhances both ambiance and functionality. These apartments offer a seamless blend of historic charm and modern luxury, making them perfect for long-term rentals or extended family living. Outside, the property continues to impress. A brick driveway and detached two-car garage includes a versatile second-story space, perfect for a home office, art studio, or creative retreat. The grounds are thoughtfully landscaped, with inviting flagstone patios and charming brick pathways winding through the tiered backyard. Enclosed with fencing, the outdoor space is designed for both privacy and enjoyment, offering cozy, intimate nooks perfect for entertaining or quiet relaxation, all while savoring the serene beauty of this historic town. Beyond its exceptional features, the Parran House enjoys a prime location in Shepherdstown, offering easy access to Shepherd University’s cultural events, the C&O Canal towpath, and a private boat dock. Nearby highlights include Antietam National Battlefield, Harpers Ferry’s outdoor recreation, Washington, D.C. commuting, and Loudoun County wineries

Set on 4+/- fenced acres with no HOA, this property offers the space, privacy, and flexibility that's becoming harder to find. Built in 2005, the home has already seen several major updates, including a newer roof (17) and updated HVAC system. While the interior is ready for fresh paint and hardwood floor refinishing, the opportunity to add your own style and improvements is reflected in the price. Hardwood flooring runs throughout the main and upper levels. The family room features a fireplace, while a second fireplace in the finished walkout lower level creates additional living and entertaining space. The lower level also includes a media room and flexible space that can adapt to a variety of needs. Outside, a large newer deck, patio, and hot tub provide plenty of room to gather with family and friends or simply enjoy the peaceful setting. The property also includes a garden area, lawn shed, and chicken house, making it well suited for small animals, or hobby farming. The spacious primary suite offers a private retreat with 2 walk -in closets and its own balcony overlooking the yard, surrounding grounds and koi pond. Whether you're looking for room to spread out, create a homestead, or simply enjoy a little more elbow room, this property offers a rare combination of acreage, updates, and potential.

OFFER DEADLINE MONDAY, JUNE 29th 6PM. Set behind a gated entrance on nearly 40 wooded acres in the hills of Berkeley Springs, The Red Gate Retreat is a remarkably private mountain retreat designed for gathering, restoration, outdoor recreation, and a slower pace connected to the surrounding landscape. Surrounded by mature hardwoods, sweeping mountain views, private trails, abundant wildlife, and a stocked fishing pond, the property offers a rare opportunity to embrace life outdoors while enjoying modern comforts. Thoughtfully positioned within the landscape are two cedar-sided residences that create a setting that feels both expansive and deeply personal. The main residence blends warmth and scale with remarkable intention. Natural wood shiplap walls, stone flooring in the kitchen, rich hardwood floors, and soaring two-story ceilings create an atmosphere that feels both elevated and grounded. Expansive windows and multiple outdoor living spaces bring the beauty of the surrounding landscape into everyday life. At the heart of the home, the chef's kitchen features Aga appliances, a large center island, generous pantry, wet bar, dedicated wine storage room, and imported Spanish tile. Designed for entertaining, the home flows seamlessly between indoor and outdoor spaces. Multiple decks overlook the pond, woods, and mountain views, while a fire pit area creates the perfect setting for evenings under the stars. The stocked pond, complete with a dock, invites afternoons spent fishing, unwinding, and making memories with family and friends. The main-level primary suite serves as a private retreat with vaulted ceilings, a dramatic stone fireplace, direct deck access, an oversized walk-in closet, and a luxurious bath featuring a steam shower, soaking tub, radiant heated flooring, and stone finishes. The great room continues the home's sense of scale with soaring ceilings and an impressive stone fireplace, while a spiral staircase leads to an upper loft ideal for a home office, reading lounge, or additional sleeping space. While there are only two legal bedrooms, the property has been thoughtfully designed to accommodate larger gatherings with several additional sleeping areas, including the loft within the main residence, featuring a built-in sleeping space, and additional accommodations within the guest residence. Positioned above the detached two-car garage, the 'upper house' offers an additional bedroom, bathroom, kitchenette and bar area, game room, and lofted sleeping space accessed by ladder—ideal for guests, multigenerational living, or potential rental income. Beyond the homes, nearly 40 acres of private recreational land await exploration. Winding trails meander through the woods, offering opportunities for hiking, wildlife observation, ATV riding, hunting, and peaceful walks beneath the Appalachian canopy. Deer, turkey, and countless bird species are frequent visitors throughout the property. Located just minutes from Sleepy Creek Wildlife Management Area and a short drive to downtown Berkeley Springs, residents enjoy easy access to hiking, fishing, boating, hunting, dining, shopping, and the area's renowned mineral springs. Smart home modern conveniences include fiber-optic internet, security cameras, Sonos audio, Lutron lighting controls, and integrated smart-home technology throughout. Refined yet deeply livable, The Red Gate Retreat offers more than a home—it offers a place to fish at sunset, explore private trails, gather around the fire with friends, and settle into a lifestyle defined by beauty, recreation, and the freedom to truly slow down.

Welcome to Equestrian Estates, a highly sought-after Winchester community with no HOA, where space, style, and flexibility come together beautifully. This stately 5-bedroom, 6-bath Colonial offers over 6,700 square feet of finished living space on nearly 3 private acres, creating the perfect setting for both everyday living and entertaining. The home was not available for showings over the past three months. During that time, several rooms were freshly repainted, and new carpet has been installed in the basement—enhancing both comfort and appeal. Originally built in 2007 and thoughtfully updated in 2020, the home shines with high-end finishes throughout, including fully renovated bathrooms featuring luxury touches such as smart toilets and heated floors in the primary suite, along with upgraded kitchen appliances. Sunlight fills the open-concept living, dining, and sunroom areas, highlighting the warm, inviting flow of the home. A dual staircase, gas fireplace, private office, and a built-in kitchen desk make the layout as functional as it is elegant. Three of the five bedrooms—including the spacious primary suite—offer private en-suite baths, providing comfort and privacy for family and guests alike. The fully finished lower level adds 1,714 square feet of living space and features two generous flex rooms ideal for guests, a home gym, or creative workspace, plus a second kitchenette, full bath, and theater room. With private walkout access, this level is perfectly suited for entertaining or multi-generational living. Outdoor living is just as impressive, with expansive decks, a beautifully designed hardscape patio set away from the home with a wood-burning chimney stack, and a flourishing garden that adds charm and privacy. A three-car garage, quiet cul-de-sac location, and easy access to Route 50 and downtown Winchester complete this exceptional offering. This is a home that truly delivers on space, elegance, and lifestyle flexibility—inside and out.