luxury houses for sale Winchester, United States

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.

Set against sweeping Blue Ridge Mountain views, this 5-acre retreat offers the opportunity to live a more intentional, inspired lifestyle — whether as a spacious 5-bedroom, 3.5 bath family home, a thriving homestead with income-producing Airbnb, or peaceful weekend retreat for creatives and nature lovers alike. Whatever the vision, it can be realized here. Built in 2004, the home welcomes morning light and ends each day against mountains illuminated by twilight. Inside, the details are deliberate and well-crafted, creating a balance of warmth, openness, and everyday functionality. Enter into the Great Room, where a soaring pine-finished vaulted ceiling and dramatic wall of windows create a warm, light-filled gathering space. The dining area flows into the well-appointed kitchen, featuring granite countertops, premium locally-made cabinetry, a large island with seating, coffee bar, oversized pantry, and adjacent laundry room. The spacious main-level primary suite is privately positioned to capture sunrise views and features an updated ensuite bath, enormous walk-in closet, and additional second closet. Upstairs are 3 generously sized bedrooms and a full bath. Multiple walk-in closets, oversized windows that frame valley views and fill the rooms with natural light, and a charming reading nook overlooking the living room below all enhance this level. The lower level continues the home’s remarkable flexibility, offering a fully separate living space with 1 bedroom, 1 bath, living room, and kitchenette. Currently operating as a successful 5-star rated Airbnb, this area could serve as multigenerational living or an au pair suite. High-speed fiber optic connectivity also supports a homeschool space, or office, complete with its own exterior entrance. At the rear of the lower level is a large pottery studio featuring new wide-plank neutral LVP flooring. Ideal for artistic pursuits, it could easily transition into a yoga studio, gym, office, or additional flex space. A large unfinished storage area completes this level. Outside, every seed, plant, and tree has been planted with long-term stewardship in mind, designed to nourish, sustain, and grow more beautiful with time. The 4,200-square-foot fenced garden follows permaculture principles that mimic nature and support regenerative practices. Curved planting beds naturally slow and absorb rainfall into the soil. Wander the mulched pathways to harvest fresh vegetables, fruits, culinary herbs, medicinal plants, and perennial flowers, all cultivated without pesticides since 2022. Beyond the garden lies an orchard planted, while a winding path leads to a tucked-away clearing ideal for a tent, yurt, or quiet evening beneath the stars. Located just 7 miles from historic Strasburg and 90 minutes from Washington DC, the property offers both retreat and accessibility. Enjoy easy access to hiking in Shenandoah National Park, the Shenandoah River, local wineries, farm markets, and the charm of the Shenandoah Valley lifestyle.

Set within the vibrant community of Lake Frederick, this beautifully appointed 4-bedroom, 2.5-bath home offers the best of many worlds — a private haven within an active neighborhood, and a lifestyle that is equally convenient as it is adventurous, with access to the lake, hiking trails, and mountain views, alongside the perk of a pool, clubhouse, and community amenities. Built just 7 years ago, the house was thoughtfully sited and designed to maximize natural light. Offering nearly 3,000 square feet of finished living space, this home stands apart with large windows, tall ceilings, warm wood tones, and thoughtfully upgraded finishes. The open-concept main level offers both connection and comfort, with the kitchen at the heart of the home. Crisp white cabinetry, pantry, and a large center island with counter seating flow seamlessly into the dining and living areas. Anchored by a gas fireplace, the Living Room is an effortless gathering space for everyday living and entertaining alike. Wrapped in windows, the Dining Room is perfect for sunny breakfasts or lively dinner gatherings that drift outside to the deck, which has been transformed into a garden filled with herbs, perennials and fruit trees. Also on this level are two rooms, currently serving as an art studio and library, yet could become a formal sitting or dining room, home office, or playroom. Upstairs, the spacious primary suite is positioned to capture morning light and mountain views, complete with two walk-in closets, dual vanities, and a tub-shower bath. Three additional generously sized bedrooms provide peaceful retreats, each filled with natural light and ample closet space. A full bath and a convenient upper-level laundry room complete this level. The unfinished lower level, complete with rough-in plumbing, French doors, and large windows, offers exceptional potential for future expansion tailored to the next owner’s vision. Enjoy Food Truck Fridays, movie nights, concerts, and community events throughout the year and drive around the corner to Region’s 117, one of the area’s sought-after restaurants. Ideally located just 20 minutes from Winchester, 10 minutes to Front Royal and I-66, the home also offers easy access to the Shenandoah River, Shenandoah National Park, historic towns, wineries, breweries, and endless outdoor recreation.

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!

With over 1,000 feet of direct North Fork Shenandoah riverbank access, this 55-acre property offers a balanced mix of open pasture and mature woodland. In 2017, the current owners constructed a custom home designed to complement the setting, supported by additional structures including a renovated 19th-century bank barn guest house, a detached three-bay garage, and a separate tractor barn. The residence was built to exacting standards using 2x6 framing, stone and HardiePlank siding, custom exterior doors, and locally milled hardwood flooring installed by Cochran’s of Berryville using lumber harvested from the property. The home offers 3,174 square feet of above-grade finished living space with three bedrooms, two full and two half baths, and a layout that places all primary living areas on the main level. An unfinished lower level provides approximately 850 square feet of storage with potential for future finishing, along with an additional one-car garage. Antique doors sourced from around the world are incorporated throughout the home. The gourmet kitchen features a wood-topped center island and tumbled stone tile flooring, opening to a sitting area with wood-burning stove. This space flows directly to a deep, full-width, northeast-facing covered porch with elevated views of the river and surrounding mountains. Quality fixtures and fittings are used throughout, including William Morris wallpaper in select rooms. A two-car side-load attached garage is complemented by a 40’ x 24’ detached three-bay garage suitable for equipment and storage. The 60’ x 30’ tractor barn, with an attached mechanicals room, offers flexible space for a variety of future uses. Just below the porch, a tiered outdoor entertaining terrace includes an expansive concrete patio, integrated stone seating, landscaped beds, and a substantial wood-burning masonry fireplace set against a private wooded backdrop. The circa 1830 bank barn, served by its own well and septic system, has been converted into guest accommodations featuring a kitchen, raised stage, sleeping quarters, one full and one half bathroom, cathedral beamed ceilings, and a second floor mezzanine/gallery, spanning much of the open interior. A private riverfront property with acreage, multiple structures, and broad scenic views, located just over an hour from Washington, D.C.

Prime Development Opportunity | 122 Acres Adjoining Industrial Park Future Potential: Strategically located for value appreciation, with an estimated post-rezoning value multiples of the current asking price. Planning & Annexation: Property is currently zoned AOC and has been officially adopted into the Berryville Area Development Authority (BADA) plan for future annexation by the Town of Berryville and Clarke County. Key Features: Adjoins the existing Clarke County Industrial Park and includes a large historic bank barn. Important Note: The existing house is unsafe for entry. Showings are by appointment only