Browse All Middleburg VA Historical Properties for Sale

This property is going to onsite auction 12/5/2026 at 11:00 AM and is being sold with reserve. LISTED PRICE IS ONLY A SUGGESTED OPENING BID AND IS NOT INDICATIVE OF THE FINAL SALES PRICE WHICH WILL BE BY SELLER CONFIRMATION DAY OF AUCTION. Terms: Down payment of $30,000 required day of auction. Settlement on or before March 1, 2027. Transfer taxes to be paid by buyer. Real Estate taxes shall be prorated. Auction Parcel #1 is a beautiful 12.15-acre country property featuring a recently remodeled 2-bedroom, 1-bathroom home, traditional bank barn, and a desirable combination of open/tillable land and woodland! Nestled in a peaceful, private setting, this property offers breathtaking mountain views and plenty of opportunities for farming, livestock, hunting, recreation, or a country retreat. The home is serviced by a private well and septic system. This exceptional property provides a rare opportunity to own a beautiful piece of countryside with acreage, privacy, and endless possibilities! Excellent location in an agricultural & recreational area only 15 minutes from Mifflinburg, 10 minutes from Penns Creek & Middleburg! Adjacent 26.54 acre parcel being sold same day.

751 Bergey Rd, Middleburg

Listing courtesy of Beiler-Campbell Realtors-Quarryville. Contact:

$89,000

3 Beds ⋅ 2 Baths

Give this diamond in the rough a look. The previous owner began remodeling and it's just waiting for someone to finish it. An oversized one car garage for off-street parking and an open yard with plenty of space.

163 W Market St W, Middleburg

Listing courtesy of Ameriquest Realty Limited. Contact:

$525,000

2 Beds ⋅ 1 Baths

A Little Slice of Horse Country Charm Cozy, charming, and full of possibilities, this delightful bungalow is surrounded by the rolling horse farms and timeless beauty that make Middleburg and Virginia’s Hunt Country so special. Set on just over an acre, the property offers a wonderful opportunity to enjoy country living with the flexibility to make the space your own. One of the home’s most inviting features is the sun-drenched, conditioned sunroom—a space you may never want to leave! Whether you envision a peaceful retreat for morning coffee, an indoor garden, a home office, or an intimate dining area, this versatile space adds warmth and valuable additional living area. Outside, mature trees, classic stacked-stone fencing, and a long gravel driveway create an unmistakable country setting. The three car garage provides space for any hobbies'st shop or simply for your vehicles. Inside, a renovated kitchen, newer roof, and updated systems offer peace of mind and make this charming home ready to enjoy. Perfectly positioned to embrace the best of Hunt Country living, you’re just minutes from historic Middleburg, and the picturesque village of Upperville, with scenic country roads, renowned horse farms, local shops, and wonderful dining all close at hand. Whether you’re searching for a full-time residence, a weekend escape, investment property or a place to enjoy the beauty and slower pace of Virginia’s countryside, this charming bungalow offers a rare blend of character, convenience, and opportunity.

6384 John Mosby Hwy, Middleburg

Listing courtesy of Corcoran McEnearney. Contact:

$1,499,900

Wonderful commercial opportunity to purchase a mixed use building fully rented in downtown historic Middleburg. This unique building anchors the corner of Madison and Federal Streets just one block south of the stoplight in the middle of town. Great investment property that offers two wonderful commercial store fronts facing Madison Street and 4 residential rental units accessed off Federal Street. Comes with 3 private parking spaces. The building has loads of charm with a stone and stucco front, large picture windows ideal for displays, dormered upper windows, and standing seam metal roof. Walk around the corner to find brick sidewalks that lead to three separate entrances to four 1-2 bedroom upper level and lower level apartments. Ideal location for walking to restaurants, groceries, post office and more. See documents for C-2 Zoning and History District information in the Documents section. Need at least 24-hour notice to show.

17 S Madison St, Middleburg

Listing courtesy of Samson Properties. 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:

$929,000

3 Beds ⋅ 3 Baths

Tucked at the end of a quiet side street in the historic town of Middleburg, this renovated ranch-style home offers comfortable, easy living just a short walk into town. The home was extensively renovated in 2020 and has recently been freshly painted on the exterior, making it truly move-in ready. The main level features an open floor plan with a well-appointed kitchen offering upgraded countertops, stainless steel appliances and a large island for casual dining or entertaining. The adjoining dining and living areas have recessed lighting and a large picture window overlooking the rear yard. There are three bedrooms, including an entry-level primary suite, and three full bathrooms, each with ceramic tile flooring and upgraded vanities, lighting and tub/showers. The fully finished lower level offers a spacious Recreation Room, bonus room, home office, full bath and separate laundry room. Other features include energy-efficient windows and ceiling fans throughout. Outside the 0.28-acre lot offers a large open rear deck for outdoor dining and entertaining, along with a covered front porch, an attached 1-car garage and paved driveway. An easy walk into Middleburg puts shops, restaurants and the town's many events right outside your door from the Christmas Parade and Oktoberfest to the Middleburg Film Festival. The Salamander Resort and National Sporting Library are also close by. Ideal commuter location only 35 minutes to Dulles International Airport and an hour to Washington DC. A nicely renovated home in a convenient in-town location that is turnkey and ready to enjoy.

409 E Marshall St E, Middleburg

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

$1,950,000

3 Beds ⋅ 2 Baths

The Jacob Mann House, circa 1817 and once home to Middleburg’s local tanner, is a charming fieldstone residence ideally located on the eastern edge of the historic village. Rich in character and thoughtfully updated, the home offers three bedrooms and two full baths including a main level primary suite. Step inside to find original hardwood floors, two fireplaces, built-ins, custom cabinetry, and abundant natural light throughout. The designer kitchen features high-end appliances and looks out over a bright enclosed back porch overlooking a deck, the private gardens and a swimming pool. The finished walk-out lower level includes a spacious Tavern Room upgraded with exposed beams, custom cabinetry, a gas fireplace, and a mini-split system, along with a private office space and a Butler’s Pantry with more custom cabinetry and an exposed stone wall. Just steps from the main house, the restored Smoke House provides exceptional flexibility with a full bath, heated hardwood floors and a fireplace making it ideal as a guest suite, home office, artist’s studio or workout room. The fully fenced grounds offer rare privacy within town limits and are enhanced by mature landscaping, including more than 50 boxwoods, laurels, arborvitae, hollies, and pines. Other improvements include pool renovations, updated fencing, a tar-based pea gravel driveway, three mini-split systems, a retractable pool cover and a hot tub. Savor the privacy of a secluded in-town setting, while enjoying an easy walk to Middleburg’s shops, restaurants, library, and post office along with quick access to local wineries, breweries, and nearby walking trails through the Salamander Resort. Unique corner parcel on .48 acres fronts three streets and has subdivision potential. A rare opportunity to own a beautifully preserved historic home in Middleburg. Don't miss!

406 E Washington St, Middleburg

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

$1,950,000

Prime Middleburg investment opportunity in the heart of the town’s historic downtown district. Offering over 5,500 square feet of versatile commercial space, this two-story brick building enjoys excellent visibility and walkability, just one storefront south of Main Street. The property will be delivered vacant, providing an investor with the flexibility to establish a new tenant, occupy the space or reposition the building for multiple tenants. The two-story configuration, with separate front and rear entrances and staircases, is well suited for a multi-tenant strategy. The existing layout includes private offices, open work areas, conference rooms, three half baths, a supply/copy room, and a generous break room. Additional features include two private front parking spaces, town water and sewer, solid brick construction, and a standing-seam metal roof. Zoned C-2, the property offers a broad range of permitted uses, including professional offices, service businesses, retail, restaurants, fitness studios, and more. An exceptional location for investors seeking a well-located, adaptable commercial asset in one of Northern Virginia’s most established and desirable small-town markets. Restaurants, shops, grocery store and the post office are all within easy walking distance. See documents section for C-2 zoning and historic district information.

6 Pendleton St, Middleburg

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

$1,100,000

2 Beds ⋅ 2 Baths

LOCATION, LOCATION, LOCATION-- 208 Chestnut Street — where comfort, community, and character come together in one perfect Middleburg address. Welcome to 208 Chestnut Street, a charming retreat nestled in the heart of Middleburg, Virginia. This unique home blends small-town charm with modern comfort — perfectly situated just steps away from the boutiques, restaurants, and equestrian culture that make Middleburg one of Loudoun County’s most desirable destinations. Step inside to find a bright, open-concept living space filled with natural light, hardwood floors, fireplace, french doors, and more. Outside, the property offers a private backyard oasis — perfect for outdoor dining, gardening, or simply relaxing under the Virginia sky. The front porch captures the essence of Middleburg living, inviting you to slow down and enjoy the charm of this picturesque village. Located within walking distance to local shops, dining, and the renowned Middleburg Farmers Market, this home offers a rare opportunity to experience the best of country living with convenient town access. It's literally, steps away from The Salamander Resort!

208 Chestnut St, Middleburg

Listing courtesy of Century 21 Redwood Realty. Contact:

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Middleburg Historical Real Estate

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Browse All Middleburg VA Historical Properties for Sale

Middleburg Historical Real Estate

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