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$2,600,000
4 Beds ⋅ 6 Baths ⋅ VALO2112484 MLS
AUCTION BIDDING OPEN: Bidding ends January 27. Previously listed at $4.25M. Current high bid $1.95M. Showings available daily by appointment. A rare opportunity to own an extraordinary piece of Virginia history on this private 37-plus acre estate minutes from historic downtown Middleburg. The Nathan Ayer House, a distinguished Colonial built in 1790 in Connecticut and meticulously relocated to hunt country, showcases unparalleled craftsmanship with nine original stone fireplaces, hand-hewn exposed beams, and authentic period hardware throughout. Lush perennial gardens and an inviting heated pool create an idyllic retreat, while the late 19th-century bank barn—constructed from hand-hewn oak and poplar with fieldstone—offers limitless potential for equestrian pursuits, entertaining, or creative endeavors. Direct frontage along Goose Creek provides ultimate seclusion on this incomparable property where architectural heritage and countryside elegance converge in perfect harmony.

35571 Millville Road, Middleburg
$1,850,000
4 Beds ⋅ 5 Baths ⋅ VALO2100252 MLS
Tucked away behind two stately willow oaks in sought-after Middleburg Downs is "Northwood" offering quiet elegance just minutes west of historic Middleburg. This classic brick Colonial, built in 1977 and thoughtfully renovated over the years, features over 3,500 square feet of finished space on two levels with 4 bedrooms, 3 full baths, and 2 half baths. The front paved parking area is framed by mature boxwoods and leads to lighted brick steps and an impressive columned front porch. Inside, the traditional center-hall layout includes a formal dining room with crown molding and chair rail and a living room with a wood-burning fireplace. Just beyond is a cozy family room with wood-paneled walls, built-ins and another fireplace. The spacious kitchen offers stainless steel appliances, island, custom cabinetry and a charming breakfast nook with views of the rear brick patio, garden beds and expansive lawn. Additional main-level highlights include a screened porch with ceramic tile flooring, two half baths, a mudroom, and a laundry room with access to the garage. Upstairs, the primary suite boasts a spacious sitting area, walk-in closet and a private bath. Two guest bedrooms share a full hall bath, while a fourth bedroom—currently used as a home office—includes two walk-in closets, built-ins and its own full bath. The beautifully landscaped grounds feature mature trees, a fenced vegetable and cutting garden with a garden shed and multiple outdoor seating areas. The rear patio with a fountain offers a perfect setting for entertaining or relaxing in total privacy. Move-in ready and ideally located, Northwood is a rare find just minutes West of downtown Middleburg.

23358 Dover Road, Middleburg
$1,849,000
3 Beds ⋅ 4 Baths ⋅ VALO2125122 MLS
Set within the heart of Virginia’s Hunt Country, Goose Berry offers an exceptional blend of charm, privacy, and natural beauty just minutes from Middleburg. Tucked within an extremely private setting on a quiet country lane, the property enjoys a truly storybook atmosphere with spectacular views of historic Goose Creek. Surrounded by mature landscaping, stone walls, and sweeping water views, the property features a spring-fed pond, multiple decks, and beautifully curated outdoor spaces designed for peaceful country living and entertaining alike. Ideal as either a full-time residence or a luxurious weekend retreat, the setting is both serene and remarkably convenient. The stucco and wood residence is rich in character, showcasing wide-plank pine floors, custom-painted interiors, and elegant imported finishes throughout. The main level centers around a chef’s kitchen with Carrara marble countertops, a butcher block island, premium appliances, and vintage Italian lighting. Gracious living and dining spaces flow seamlessly together, while the sun room is filled with natural light and opens directly to expansive decks overlooking the water and surrounding landscape. A wood-burning fireplace, custom window treatments, and Murano lighting from Venice further elevate the home’s sophisticated yet inviting atmosphere. Upstairs, the spacious primary suite offers a walk-in closet and luxurious bath with a soaking tub and oversized shower, accompanied by an additional guest bedroom and bath. The lower level includes a family room with custom built-ins, French doors opening to the deck, and a third bedroom with an updated en-suite bath. Equestrian amenities include a custom three-stall barn with tack room, wash stall, feed room, hay loft, and a charming one-bedroom apartment complete with full kitchen and living space. There is a large paddock off the barn Located within Middleburg Hunt territory with access to nearby riding and walking trails, this exceptional property offers the very best of Hunt Country living just minutes from historic Middleburg.

22065 Whitetail Ridge Lane, Middleburg
$432,000
VALO2121224 MLS
Sellers are asking for highest and best by 5pm on 4/23/26. Discover an exceptional opportunity to build a custom estate on 3.57 acres of beautifully level, open land just moments from the heart of Middleburg, Virginia. Perfectly positioned in one of Loudoun County’s most sought after enclaves, this property offers the rare combination of privacy, convenience, and build ready topography—an ideal canvas for a luxury residence. This parcel sits in the heart of Virginia’s renowned horse and wine country, where rolling landscapes meet refined country living. Whether you envision a modern farmhouse, a classic Virginia manor, or a weekend retreat, the land’s level grade and generous dimensions allow for exceptional design flexibility. The lot is scheduled to be Bush Hogged in the next few weeks. This is in the Middleburg Downs Residents Association ask listing agent for information . •

Lot 46 Middleburg Downs, Middleburg
$290,000
4 Beds ⋅ 2 Baths ⋅ PASY2002754 MLS

310 S Shuman Street, Middleburg
$197,000
4 Beds ⋅ 2 Baths ⋅ PASY2002610 MLS
Secluded 9+ wooded acres in beautiful Snyder County. Want a quiet get-away? a great hunting spot? A quiet place to live in a country setting? This is the place for you. The house is spacious with a vaulted ceiling in the living room with a large stone fireplace. The kitchen has a woodstove with an attractive stone hearth. This is a perfect opportunity to add your own style and finishes. Basement could have finished space again, and opens to a nice side yard. Pool needs work or could be filled in. Up on the hill is a cute horse barn and paddock area ready for your animals. This is a rare opportunity. Don't wait!

550 Greenhouse Road, Middleburg