Browse All Middleburg VA 5 Bedroom Properties for Sale

Rarely does a horse property of this caliber become available in Middleburg, Virginia. Located just minutes west of town, this exceptional 100+ acre farm is anchored by a gracious 9,500+ square-foot main residence spanning three levels, offering five bedrooms including a guest apartment on the main level. Potential for a home office with separate entrance and full bath in the basement that is currently being used as a gym. A renovated chef’s kitchen, updated baths, reclaimed wide-plank hardwood floors, 10-foot ceilings, refined lighting, and fresh paint leave this home polished and move in ready. Heated pool with electric cover and pool house, along with two 2-car garages. The extraordinary equestrian facility is what truly sets this property apart. An exceptionally built 12-stall center aisle stucco barn with Classic Equine Stalls features two wash stalls, tack room with custom cabinetry and granite counter tops, office, laundry with full bath, feed room, blanket room, and three car garage. Above is a beautifully appointed two-bedroom apartment along with a rider's lounge, as well as two large haylofts with hay drops. The entire second floor is concrete, and both the apartment and lounge have a commercial fire rating. Steps from the barn is a 200' x 100' covered riding arena with mirrors and a 6-horse Kraft walker with central round pen, both with custom footing and lights. Nine fenced paddocks with run-in sheds, an additional 2-stall convertible barn and excellent ride-out complete the equestrian amenities. The very large three-bay equipment shop and pond round out this remarkable Middleburg farm. There are two large generators that run the entire house and barn complex. Multiple wells on property are interconnected to ensure backup water to house and barn. High speed fiber throughout. Extensive trails and entire east side of the property is bordered by Cromwell’s Run creek. The farm is located in Northern Fauquier County, within the Orange County Hunt and is in a VOF conservation easement. See documents section for floor plans and more. Be sure to watch the video! <iframe src="https://listings.upwardstudio.com/videos/01a11163-2247-706c-a6fc-ae20d7f55906" width="640" height="360" frameborder="0" allow="autoplay; fullscreen; picture-in-picture" allowfullscreen style="border: 0"></iframe>

1663 Hatchers Mill Rd, Middleburg

Listing courtesy of Thomas and Talbot Estate Properties, Inc.. Contact:

$1,250,000

5 Beds ⋅ 3 Baths

An exceptional and rarely available opportunity just two minutes from Historic Middleburg: two beautifully renovated homes offering the flexibility, privacy and versatility of a private family compound. Whether envisioned as a full-time residence with a separate home for multigenerational living, extended family or guests, or as an income-producing property, the possibilities are as unique as the setting. The larger residence, 37603, features three bedrooms and two full baths with thoughtfully updated interiors throughout. The main level centers around a beautifully renovated kitchen with a generous island, stone countertops, tile backsplash and accent wall, stainless steel appliances, and an inviting connection to the dining area. A separate family room is anchored by a wood-burning fieldstone fireplace, creating a warm and comfortable gathering space. The main-level primary suite features a beautifully renovated ensuite bath with sophisticated finishes, including a seamless glass shower enclosure surrounded by floor-to-ceiling tile. Two additional bedrooms upstairs share another fully renovated bath. Outside, a private paver patio provides an inviting setting for evenings around the firepit, whether enjoying a glass of wine or making s'mores with family and friends. The second residence, 37609, offers two bedrooms and has been equally well cared for and renovated. The stylish kitchen features stone countertops, a modern tile backsplash, stainless steel appliances and recessed lighting, while the adjoining breakfast area opens to a cozy family room. French doors lead to a private paver patio, perfect for alfresco dining, morning coffee or unwinding with a glass of wine after exploring the surrounding countryside. Upstairs, two bedrooms share a beautifully renovated full bath. Two outdoor sheds offers additional storage space & can serve as perfect gardening sheds. Together, these two residences create a truly special Western Loudoun retreat with an extraordinary combination of flexibility and proximity. Just minutes from the boutiques, restaurants, wineries and equestrian charm of Historic Middleburg, as well as the renowned Salamander Resort & Spa, this is an opportunity to create your own private family compound, full-time country residence, guest retreat or income-producing property—all in one of Loudoun County's most sought-after destinations.

37603 Little River Tpke, Middleburg

Listing courtesy of Real Broker, LLC. Contact:

$2,695,000

5 Beds ⋅ 5 Baths

Welcome home to Woodland Farm: a legacy equestrian estate in the heart of Loudoun County. Experience the pinnacle of Loudoun County living on this extraordinary 16-acre sanctuary. Woodland Farm offers a rare convergence of country elegance, professional equestrian facilities, and multi-generational flexibility. Pass through stately stone pillars and follow a winding paved drive that crosses a clear, spring-fed stream. Resting atop a private knoll, the custom stone and hardiplank manor commands panoramic views of rolling hills and lush pastures. This is more than a home; it is a retreat designed for both peace and presence. Inside, the home reveals a careful balance of grandeur and warmth. Sunlight pours through expansive windows beneath soaring 14-foot ceilings, illuminating spaces designed for both gathering and quiet retreat. The great room anchors the home, where floor-to-ceiling french doors open onto a sweeping pool terrace, inviting the outdoors in. At its center, a striking double-sided stone wood-burning fireplace creates a natural flow into the formal dining room, making it easy to imagine evenings filled with conversation, laughter, and celebration. Nearby, the library offers a more intimate setting, where a gas fire flickers softly during quiet conversations, while the main-level theater room promises immersive cinematic nights. The kitchen serves as the heart of it all—a place where daily life and entertaining intertwine. With its expansive social island and seamless connection to dining spaces, it becomes a natural gathering point, whether for casual mornings or lively dinner parties. The home’s thoughtful design extends to its private wings, where the east wing offers a serene primary suite alongside two additional bedrooms, while the west wing provides two oversized bedrooms each with their own ensuite bathroom, creating a sense of separation and comfort for family and guests alike. Beyond the main residence, Woodland Farm fully embraces its identity as a working equestrian estate. A five-stall center aisle barn stands ready for daily routines, complemented by a fenced riding arena and four well-maintained paddocks that support rotation and turnout. The land itself invites exploration—gentle acreage for riding, wooded trails for wandering, and the ever-present stream offering a place to pause and reflect. There is room here not just to live, but to grow, with space for future barns, arenas, or expanded facilities. Enjoy warm summer days gathering around the pool, where wide stone patios and covered wood decks set the stage for long Virginia evenings under open skies. And tucked away with their own entrance and parking, two private guest apartments overlook the woods and stream, offering flexibility for extended family, rental opportunities, or a peaceful remote workspace. Though the property feels deeply secluded, it remains closely connected to the world beyond. Starlink high-speed internet supports modern living, while the nearby village of Middleburg provides access to fine dining, charming boutiques, and the surrounding wine country. Woodland Farm is a place where elegance meets function, where open land meets thoughtful design, and where each day carries a sense of both escape and belonging.

38386 Little River Tpke, Middleburg

Listing courtesy of MAXVALUE, REALTORS. Contact:

$3,875,000

5 Beds ⋅ 7 Baths

Stunning custom-built offering over 10,000 sq. ft. across three levels, combining exceptional craftsmanship, advanced technology, and refined design. Set on a beautiful homesite in Middleburg, this 2x6 constructed residence features wide-plank hardwood floors throughout the main and upper levels, 8-ft interior doors, and ceiling heights of 10 ft on the main level and 9 ft on both the upper and lower levels. The main-level primary suite includes a private sitting room with fireplace, custom walk-in closet with built-ins, and a spa-style bath with dual sinks, an oversized walk-in shower with benches, and elegant finishes. A second primary suite on the upper-level offers a private sitting room, three large walk-in closets with built-ins, vaulted ceilings, a spacious spa bath with separate his-and-her toilet rooms, dual vanities with tower storage, an extra-large shower with benches, and a soaking tub. Three additional en-suite bedrooms feature generous walk-in closets; two include showers with benches and one includes a tub/shower. The gourmet kitchen features a Wolf wall steam oven, Wolf warming drawer, 36" Sub-Zero column refrigerator and freezer, 24" Sub-Zero wine column, under-counter beverage center, and hardwood flooring. The home is wired with ceiling speakers throughout and includes Comcast high-speed internet. The partially finished lower-level features matching wide-plank–style LVT flooring, 9-ft ceilings, and flexible spaces for recreation, fitness, along with future customization. A 5-ft fire-rated Liberty safe also conveys. The Guardian security system includes whole-house water shutoff with sensors, 8 exterior recording cameras, an IP/cloud system, and a wall-mounted interface for control. Mechanical systems include high-efficiency Trane HVAC units with fresh-air replacement and air scrubbers, tankless hot water heaters, a 1,000-gallon propane tank (Valley Energy auto-fill), and wiring for a whole-house generator. Garages include two mini-split systems for climate control and two 240V EV charging receptacles. The home is served by a 55 gpm well and a 5-bedroom-rated septic with double-tank system, with an Architectural shingle roof for peace of mind. Oversized circular driveway (approx. 20 ft wide) includes a second asphalt top coat recently added by builder. First-year builder warranty and a paid HVAC service plan through 2026 are included. Additional features include Climate-controlled garages, wide-plank wood floors throughout, built-in closet systems, ceiling LED lighting in all bedrooms, and chandeliers in the upper-level primary suite and bath. All three levels offer functional, flexible layouts and high-end finishes. This newly built Middleburg home offers luxury, advanced home systems, and thoughtful design throughout—ready for immediate enjoyment. Certain furnishings are available for purchase under a separate bill of sale

37291 Seabiscuit Park Pl, Middleburg

Listing courtesy of Corcoran McEnearney. Contact:

$3,899,900

5 Beds ⋅ 4 Baths

A completely reimagined estate designed in collaboration with renowned Middleburg architect Timothy Clites. This modern farmhouse is a breathtaking fusion of refined luxury and timeless equestrian elegance, set on 12 acres in the coveted Atoka Chase community with paved roads. An entry framed by original historic stone walls leads to a home and barn cottage that has been completed to the highest standard, surrounded by expansive stone porches capturing panoramic views of rolling pastures and the Blue Ridge Mountains on all sides. Every room was intentionally positioned to frame the intensely beautiful sunrises and sunsets, offering panoramic views from every window and filling the home with natural light from dawn to dusk. Inside, the thoughtful floorplan blends traditional craftsmanship and contemporary sophistication with oak hardwood flooring, shiplap walls and ceilings, vaulted spaces featuring exposed antique beams sourced from local barns, custom closets, designer lighting, heated tile floors and ceiling fans throughout. The main-level primary suite offers incredible western sunset views, a private outdoor screened porch and a bath with heated floors and towel racks. A study with a wood stove and an adjacent office/guest suite is equipped with high-speed fiber internet for seamless remote work and access to an additional full bath all on the main level. The chef’s kitchen is both striking and efficient, featuring heated floors, a gas range, two dishwashers, ice maker and stainless-steel appliances. French doors off the mud room open to the rear covered porch and outdoor kitchen offering a one and only outdoor entertaining space. The living room centers around a dramatic stone wood-burning fireplace, pool views to one side and mountain views out the other. The upper level includes three additional bedrooms and two full baths, each with hardwood flooring, heated tile floors and towel warmers. Large dormer windows provide abundant natural sunlight and mountain views. Every mechanical and electrical system is updated, reflecting the level of detail and investment poured into this property. There is a large unfinished basement with a bathroom rough-in and fireplace. The outdoor living experience rivals a private resort, with a heated saltwater infinity pool and spa overlooking the pastures, Sonos surround sound system, a flagstone patio, gas firepit, a fully equipped outdoor kitchen with gas grill, refrigerator, and a dedicated ice maker. The property is a turnkey horse facility with board-fenced pastures, automatic waterers, electric fencing, run-in sheds with electric and individual two-stall barns—all lined with oak milled from Middleburg trees and clad to match the main residence for perfect visual harmony—as well as a dedicated tack room, covered parking/equipment storage, and a comprehensives smart home security system with exterior cameras for full remote monitoring and peace of mind. Every detail was curated to balance beauty, efficiency, and the ease of a true horse lifestyle. This property is more than a home; it is a masterwork of architecture, design, and lifestyle—an unparalleled Middleburg estate where luxury, privacy, and function meet.

34642 Atoka Chase Ln, Middleburg

Listing courtesy of Douglas Elliman of Metro DC, LLC. Contact:

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Browse All Middleburg VA 5 Bedroom Properties for Sale

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