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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.

4 Beds ⋅ 6 Baths

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 Rd, Middleburg

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: TTR Sotheby's International Realty.

$1,849,000

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.

3 Beds ⋅ 4 Baths

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 Ln, Middleburg

Listing courtesy of Washington Fine Properties, LLC. Contact:

Selling Office: Washington Fine Properties ,LLC.

$432,000

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

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Washington Fine Properties, LLC.

$290,000

4 Beds ⋅ 2 Baths

310 S Shuman St, Middleburg

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Non Subscribing Office.

$197,000

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!

4 Beds ⋅ 2 Baths

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 Rd, Middleburg

Listing courtesy of Cavalry Realty LLC. Contact:

Selling Office: Cavalry Realty LLC.