Browse All Middleburg VA Historical Properties for Sale

Looking for a ranch home on a spacious lot with plenty of room to enjoy the outdoors? This home offers easy, one floor living & a large backyard perfect for relaxing or entertaining. Inside, you'll find hardwood floors under the carpet (excluding the kitchen & bathroom), just waiting to be uncovered. The full basement provides storage space, along with existing laundry hookups. Laundry has been relocated to one of the bedrooms for convenience but can easily be moved back to the basement. Located just minutes from Selinsgrove & Middleburg, this home offers comfort & convenience. Whether you're looking to downsize or just starting out, this is a wonderful opportunity to make it your own! Square footage taken from Snyder County Assessment office.

124 Vine St, Middleburg

Listing courtesy of Bowen Agency, Inc.. Contact: 5707432165

$948,800

5 Beds ⋅ 3 Baths

Tucked beneath mature shade trees in the heart of Middleburg, this five-bedroom farmhouse pairs historic character with thoughtful updates. Inside, original heart pine floors run throughout, paired with tall windows, deep crown molding, and the kind of vintage cast-iron radiators that give old Virginia homes their warmth. The front living room centers on a wood-burning fireplace with a classic painted mantel, while the adjoining dining room offers built-in shelving and a capiz-shell pendant overhead. The kitchen presents a well-sized blank slate, ready for a future owner's personal touch. A first-floor bedroom adds welcome flexibility for guests, in-laws, or main-level living. Upstairs, four additional bedrooms share the same wide-plank floors and generous natural light, served by two full baths with tiled shower surrounds, rounding out the home's three full baths. Outside, the aerial view tells the rest of the story: a quiet, tree-canopied street lined with charming homes, open pasture and the Blue Ridge foothills rolling out just beyond town. It's classic Middleburg — walkable, historic, and horse-country close, minutes from the village's shops, restaurants, and wine country beyond. A rare opportunity to own a piece of Middleburg's architectural character with modern-day livability already built in. Note: a new HVAC/AC system is already scheduled for installation, taking one more item off the new owner's to-do list.

107 Walnut, Middleburg

Listing courtesy of Corcoran McEnearney. Contact: 5406876321

$795,000

4 Beds ⋅ 3 Baths

Also know as 1548 Weston Lane. Charming stucco cottage beautifully renovated from top to bottom in 2026, offering the perfect blend of timeless character and modern comfort. Ideally located just minutes from Middleburg with convenient access to Route 50, this turnkey home features 3 bedrooms and 3 full baths, thoughtfully designed for easy living. The bright, updated interior includes a new gourmet kitchen, a welcoming living room with fireplace, and a cozy den. The fully finished lower level offers a second kitchen, creating an ideal space for a guest suite, in-law accommodations, or potential rental opportunity. Enjoy outdoor living on the expansive wrap-around deck overlooking a fenced backyard—perfect for dogs—and beautifully landscaped gardens. A rare opportunity to own a completely renovated cottage in a sought-after location. See attached documents for a complete list of improvements.

6428 John S Mosby Hwy, Middleburg

Listing courtesy of Sheridan-MacMahon Ltd.. 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: 5406876500

$299,000

4 Beds ⋅ 2 Baths

310 S Shuman St, Middleburg

Listing courtesy of EXP Realty, LLC. Contact: 8883977352

$330,000

Situated on 2.9 private acres, this property offers a rare opportunity to finish and customize to your vision. Featuring a newly constructed crawl space and brand-new floor joists already in place, much of the foundational work has been started for you. Bring your ideas and complete this home exactly the way you want it. Plenty of space for gardening, recreation, or simply enjoying the peaceful setting.

21964 St Louis Rd, Middleburg

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

$1,625,000

3 Beds ⋅ 3 Baths

Circa 1938, this storybook stone and frame residence is beautifully nestled in the heart of the village of Middleburg, where timeless elegance and small-town charm converge. Meticulously restored to an exceptional standard, the home exudes warmth, character, and understated luxury, offering 3 bedrooms and 2½ baths in pristine, turnkey condition. From the moment you enter, you are welcomed by rich hardwood floors and an inviting ambiance that speaks to the home’s heritage. The gracious living room, centered around a classic fireplace, provides the perfect setting for intimate gatherings, while the thoughtfully appointed gourmet kitchen blends style and function, ideal for both everyday living and refined entertaining. Step outside to discover a truly enchanting setting. The expansive lot is adorned with lush, mature gardens that offer a tapestry of color through the seasons, creating a private oasis in the middle of the village. A charming side porch invites you to unwind with morning coffee or evening cocktails, surrounded by the beauty of the landscape. Completing the property is a detached two-car garage with a versatile workshop, offering ample space for hobbies or storage. Rarely does a home of this caliber and character become available—an extraordinary opportunity to own a piece of Middleburg’s charm, where history, beauty, and modern comfort come together effortlessly.

700 W Washington St, Middleburg

Listing courtesy of Sheridan-MacMahon Ltd.. Contact:

$449,900

2 Beds ⋅ 1 Baths

SINGLE FAMILY HOME FOR CONDO PRICE-BUT NO CONDO FEE -NO HOA- FEE. Welcome to “The Pink Cottage” — A Sunny Retreat Just Minutes from the Heart of Middleburg on half acre lot! Tucked away in the scenic countryside just 8 minutes to downtown Middleburg, this cheerful and sun-drenched cottage offers a perfect blend of charm, convenience, and tranquil living. Located in the heart of Virginia’s renowned horse and wine country, you'll enjoy quick access to all the delights of historic Middleburg—a town celebrated for its boutique shopping, fine dining, art galleries, equestrian events, and luxurious destinations like Salamander Resort. Step inside this lovingly cared-for home and you'll be greeted by warm wood floors, abundant natural light, and picturesque views of the western mountains from the front living room window. The thoughtful layout includes two main-level bedrooms a refreshed full bath, offering true main-floor living that’s both functional and inviting. The updated kitchen features newer appliances (propane gas cooking) and a cozy, efficient layout that opens onto the rear deck—an ideal spot for sipping morning coffee or hosting casual gatherings while enjoying the expansive yard and mature landscaping. Downstairs, the enormous unfinished basement has been professionally waterproofed (2024) with a full dehumidifier system, sump pump with battery backup, and interior French drain—offering incredible storage space with walkout door. Additional recent updates include light fixtures (2024). Insulation Kitchen water pipes (2026) New water heater (2024) and a NEW whole-house water treatment system with filters and softener (2024) and newer windows. Gardeners will love the designated space for planting, while horse lovers will appreciate being close to multiple boarding facilities. This home offers peaceful living in one of Virginia’s most desirable countryside communities. Owned by two licensed VA Realtors. Property has strong rental history-@ $2450.00 a month .NO HOA. GRASSY AREA TO RIGHT OF HOME IS PART OF PROPERTY TO THE GRAVEL ROAD

22282 St Louis Rd, Middleburg

Listing courtesy of On The Market Properties. Contact: 7034084261

$2,250,000

Prime commercial investment opportunity in the heart of Middleburg’s downtown historic district. Over 5,500 square feet, located one storefront south of main street with excellent visibility and walkability. The building will be delivered vacant, as the current tenant is relocating within town. Two-story layout with front and rear entrances and staircases allows for multiple tenants or flexible use. Features include private offices, open work areas, conference rooms, three half baths, supply/copy room and large break room. Two private parking spaces in front. Solid brick construction with standing-seam metal roof. Zoned C-2, permitting professional offices, service businesses, restaurant, retail, fitness studio, and more. Town water and sewer. Walk to restaurants, shops, grocery, and post office. See documents section for C-2 zoning and historic district details.

6 Pendleton St, Middleburg

Listing courtesy of Thomas and Talbot Estate Properties, Inc.. Contact: 5406876500

$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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