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$2,195,000
4 Beds 5 Baths VALO2132296 MLS
Perfectly positioned on the eastern edge of the historic village of Middleburg, this extraordinary custom-built estate captures the timeless character of Virginia's horse country while embracing the comfort, craftsmanship, and sophistication of modern living. Built in 2021, the home was thoughtfully designed to honor the architectural traditions that define this remarkable region, blending classic proportions, natural materials, and refined detailing into a residence that feels both timeless and elegant. <br><br> Surrounded by gently rolling countryside and open skies, the setting offers exceptional privacy while remaining just minutes from Middleburg's acclaimed restaurants, boutiques, wineries, equestrian venues, and commuter routes. Here, mornings begin with sweeping pastoral views, evenings end beside a crackling fire, and every season brings a new appreciation for the landscape. <br><br> A welcoming front porch introduces interiors filled with warmth and exceptional craftsmanship. Wide-plank hardwood floors, soaring ceilings, custom millwork, abundant natural light, and carefully curated finishes create an atmosphere of understated luxury throughout. <br><br> Just beyond the foyer, a remarkable private office showcases dramatic painted millwork, custom built-ins, elegant lighting, and walls of windows overlooking the countryside, creating an inspiring space for work or quiet reflection. <br><br> At the heart of the home, the chef's kitchen was designed for gathering and everyday living. Premium appliances, extensive custom cabinetry, an oversized center island, and an exceptional walk-in pantry provide beauty and function. The adjoining dining area and keeping room center around a handsome wood-burning fireplace, while expansive windows showcase breathtaking countryside views. <br><br> French doors open to an exceptional stone terrace designed for entertaining and relaxation. A fully equipped outdoor kitchen, wood-burning fireplace, and thoughtfully designed gathering spaces create the perfect setting for intimate dinners or memorable evenings beneath Virginia's open skies. <br><br> The upper level provides a peaceful retreat where every bedroom offers generous proportions, elevated ceilings, abundant natural light, and tranquil views. The luxurious primary suite features a spacious sitting area, custom walk-in closets, and a beautifully appointed spa bath with dual vanities and an oversized walk-in shower. <br><br> The finished lower level expands the home's versatility with generous recreation and theater spaces along with a private guest suite, making it ideal for entertaining or extended stays. <br><br> Complementing the residence is an architecturally striking detached three-car garage with a distinctive red exterior and carriage-style design that perfectly reinforces the property's authentic Virginia character. <br><br> Since completion, the property has been enhanced with thoughtfully selected upgrades, including a custom pantry, extensive interior millwork, designer lighting, expanded hardscaping, professionally designed landscaping, additional fencing and gates, Starlink internet, whole-home audio, Nest thermostats, three Air Scrubbers, a steam humidifier, hot water recirculation, water purification servicing, plumbing enhancements, and numerous mechanical improvements that enhance comfort and efficiency. <br><br> Middleburg has long been treasured for its equestrian heritage, scenic beauty, and enduring sense of place. Rolling fields replace busy streets, neighbors value privacy, and life moves at a more peaceful pace without sacrificing convenience. <br><br Homes of this caliber are defined not only by exceptional craftsmanship, but by the experience they create. Filled with natural light, framed by spectacular countryside views, and designed with timeless architecture and enduring quality, this is a rare opportunity to own a recently constructed custom estate that beautifully captures the spirit of Middleburg.

23232 Sally Mill Rd, Middleburg

$1,995,000
6 Beds 5 Baths VALO2131852 MLS
**35317, 35321 & 35327 Snake Hill Road | Middleburg, Virginia 20117** Whitehall is an extraordinary private Hunt Country compound just minutes from the Town of Middleburg. Thoughtfully conceived and developed over more than a decade by an experienced builder, the property spans two separately recorded parcels and offers a rare combination of luxury living, exceptional infrastructure, and remarkable flexibility. Functioning seamlessly as a single private compound, the two separately recorded parcels provide uncommon flexibility for multigenerational living, guest accommodations, rental income, future ownership, or long-term investment. The compound comprises approximately 12,500± square feet of improvements under roof, including 5,570± square feet across three principal buildings and an additional 6,940± square feet of thoughtfully designed accessory improvements, including covered porches and pavilion, utility buildings, equipment barns, equestrian facilities, and support structures. The custom-built main residence is complemented by a beautifully designed carriage house featuring a private apartment, office, fitness space, wine cellar, and finished two-car garage, while the fully renovated guest residence occupies the second separately recorded parcel. Together, the three principal buildings create an exceptionally versatile compound suited for family living, guests, staff, or income-producing opportunities. Beyond the residences, Whitehall is exceptionally well equipped with a substantial flex utility building, covered equipment barns, equestrian facilities, greenhouse, and inviting covered porches and pavilion. Unlike many country properties that evolve through unrelated additions, Whitehall was intentionally planned as a cohesive compound where every structure complements the others architecturally and functionally. Whitehall represents a rare opportunity to own one of Middleburg's most versatile private compounds, combining privacy, enduring quality, and exceptional flexibility in the heart of Virginia's renowned Hunt Country. *The square footage, bedroom count, and room count referenced in this listing reflect the combined improvements comprising the Whitehall compound, including the main residence, carriage house, and guest residence, unless otherwise noted. Buyers are encouraged to review the floor plans and building summary for the individual building layouts and dimensions.*

35321 Snake Hill Rd, Middleburg

$200,000
3 Beds 1 Baths PASY2002806 MLS
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

$405,000
VALO2128064 MLS Federal Court BLDG.
This Federal Court office condominium unit offers approximately 1,500 square feet of bright and versatile office space in the heart of historic Middleburg. Occupying a desirable corner location on the second floor, the suite enjoys abundant natural light from three directions creating a welcoming and productive work environment. Currently configured as a medical office with a large reception area and 4 separate offices, the space features non-structural interior walls that can be reconfigured to suit a variety of professional uses. Renovated in 2021, the suite offers high-quality flooring, paint, and updated lighting. It also includes a break room, powder room, separate electric metering and its own dedicated heating and cooling system. Three assigned parking spaces are located directly behind the building for added convenience. Just steps from Middleburg's charming main street, the property is within easy walking distance of local shops, restaurants, banks, the post office, the National Sporting Library & Museum, the Red Fox Inn, and Salamander Resort & Spa. Located within the Town of Middleburg's C-3 zoning district, the condominium is designed for professional office use. The quarterly condominium fee of $1,216.40 includes water and sewer service, snow removal, and trash dumpster service. Comcast Internet. See floor plan included.

107 W Federal St Unit #13, Middleburg

$948,800
5 Beds 3 Baths VALO2129326 MLS
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

$700,000
VALO2129896 MLS Town Of Middleburg BLDG.
Rare opportunity to acquire a prime commercial property in the heart of the charming Town of Middleburg. This well-maintained and thoughtfully configured space offers exceptional potential for a medical practice, doctors’ office, clinic, wellness center, or a variety of other professional uses. Encompassing approximately 1,500 square feet, the property features an efficient and highly functional floor plan, available in the documents section. The current layout includes four well-appointed exam rooms, a welcoming reception area, comfortable waiting room, two private offices, three half baths, and a dedicated file/storage room—providing flexibility to accommodate a wide range of business needs. Zoned C-1, this property offers valuable versatility for professional, office, and commercial applications. Additional highlights include a paved parking lot for ease and convenience, as well as ramp access to the building, ensuring accessibility for clients and staff alike. Positioned in one of Virginia’s most sought-after small towns, this is an outstanding opportunity to establish or expand your business in a highly desirable location with excellent visibility and accessibility. Property may be shown by appointment Monday through Friday after 4:00 PM and on weekends.

204 E Federal St Unit #B, Middleburg

$795,000
4 Beds 3 Baths VAFQ2022624 MLS
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

$1,395,000
3 Beds 3 Baths VALO2128060 MLS
Elegant design, exceptional entertaining spaces, and a private 1.21-acre setting come together in this stunning custom-built French Country residence, tucked away on a quiet dead-end lane in the sought-after location just west of Middleburg. A stately stucco exterior, Palladian-inspired window details and a soaring two-story foyer create a memorable first impression. Mahogany double doors open to a gracious foyer featuring porcelain tile flooring and a sweeping quarter-turn staircase. At the heart of the home is a beautifully appointed gourmet kitchen with stainless steel appliances, granite countertops and upgraded cabinetry. The kitchen flows seamlessly into the breakfast area and family room, where a dramatic wall of windows fills the space with natural light. A covered patio extends the living space outdoors and provides the perfect setting for al fresco dining and sunset views. Designed for both formal and casual entertaining, the home also features an elegant dining room with a bay window and arched opening to the formal living room. Upstairs, the spacious primary suite offers two walk-in closets and a luxurious spa-inspired bath with a jetted soaking tub and oversized double shower. Two additional guest bedrooms feature generous closet space and share a well-appointed hall bath. The unfinished lower level features a full-sized window and offers endless possibilities with ample space for a home office, recreation room, home gym or additional storage. Additional highlights include gleaming hardwood floors, new roof (2016), two new Trane HVAC units, water heater, and central vacuum system (2017). A two-car front-load garage and oversized driveway provide added convenience. Enjoy the best of village and country living just 3 minutes from downtown Middleburg, home to beloved annual traditions including the Middleburg Film Festival, the 1000 Miglia Warm Up USA, Oktoberfest, and Christmas in Middleburg. Nearby wineries, breweries, and a cidery offer endless opportunities to explore Virginia wine country, while commuters will appreciate the easy access to Dulles International Airport, just 35 minutes away, and downtown Washington, D.C., within approximately one hour.

36006 Little River Turnpike, Middleburg

$2,850,000
4 Beds 5 Baths VALO2126154 MLS
Set on 12.9 private, rolling acres in Virginia’s premier horse country, this well-appointed three-level stucco home perfectly pairs timeless country aesthetics with state-of-the-art modern luxury. Originally built in 1992 and topped with a premium standing-seam metal roof, the residence has been spectacularly reimagined with top-tier architectural upgrades, offering a flawless turn-key lifestyle for the discerning buyer. As you enter through the field stone columns, you are greeted with beautiful, landscaped gardens boasting established hardwoods, flowering dogwoods, weeping cherry, crabapple and redbud varieties, including large and small boxwood bushes, and various perineal plantings. This backdrop provides charm, privacy and a revolving seasonal landscape. Upon entering the home, you are immediately welcomed with style, form and function, including multiple coat closets, front and back staircases to the upper living areas, walk-in kitchen pantry and an open design concept that flows seamlessly for family and formal living. The heart of the home underwent a complete, full-scale architectural transformation, offering an effortless layout optimized for grand-scale entertaining and warm everyday life. These improvements include a gourmet kitchen with light and airy quartz countertops, a hammered stainless steel metal center island, custom cabinetry and state of the art kitchen appliances. The open-style kitchen flows into the adjoining breakfast room, den, dining, living and powder rooms highlighted with designer spaces that are uniquely styled. Hand hewn beams, custom painted hardwood flooring, shiplap walls, built in bookshelves, two working wood fireplaces, a mudroom/ laundry room and an attached two car garage are all part of this beautifully tailored home. Large windows and French doors throughout create open and airy spaces with views of the separate gardens and outdoor entertainment areas. The back deck with a lovely, draped wisteria trellis overlooks your private three board fenced rolling pastures and views to the west. The two custom-designed stairwells serve as striking centerpieces, anchoring the home's transition to the upper quarters. The upper level is designed with family and guests in mind, featuring a master suite, private guest room with full bath, a playroom/entertainment area and two additional bedrooms linked together by a jack and jill bath. This entire upper level recently underwent a complete top-to-bottom redesign showcasing antique ceiling beams, custom shiplap wall treatments, marble bathroom flooring, custom vanities with upgraded lighting and designated media areas, marrying historic warmth with clean, modern lines. Enjoy your private primary bed and spa like bath with a large dressing room off the bathroom. The primary bathroom is an oasis of luxury, anchored by premium marble tile flooring, upgraded designer lighting, and elite plumbing fixtures. Included with your turnkey home, enjoy a fully finished walk out basement living area including custom hand painted cabinetry in both the wet bar and media/den areas. These areas are enhanced with a copper sink, soapstone countertop, a field stone custom gas fireplace tv area, a separate wine room and cedar closet. Also included in this space is a large game room area, a full bathroom with stand-up shower and large storage utility rooms. Dime Box is a beautiful, private family home custom designed with indoor and outdoor living areas to embrace the breathtaking Virginia countryside.

36190 Turkey Roost Rd, Middleburg

$1,950,000
3 Beds 2 Baths VALO2126668 MLS
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

$1,525,000
4 Beds 5 Baths VALO2126322 MLS
Desirable, updated home in the Melmore neighborhood of Middleburg. Nestled on three acres, this Colonial Williamsburg home has been meticulously maintained and updated. Enter the gracious front porch into the formal foyer. To the left is the large family room with gas fireplace and built in bookcases. To the right is the formal living room with wood burning fireplace which opens to the formal dining room. The adjacent, light filled kitchen, overlooks the large back yard and includes an area for a family dining table. A large mud room/laundry room and half bath with custom vanity and lovely finishes are also found on this level. Upstairs are 4 bedrooms. The large primary bedroom has two NEWLY REMODELED bathrooms--one with a tub, the other with a walk in shower. Abundant closet space and a separate dressing area makes this suite even more desirable. One of the other bedrooms includes an en suite bath. The other two share the use of the central, upstairs full bathroom. There is a large, walk up attic space for future completion as living space or to be utilized now for added storage. There is a large deck spanning the rear of the home. The grounds have been professionally landscaped and includes mature trees, stone walls, garden beds and is fenced for the safe keeping of pets or children's play. This is truly a delightful property, well suited for family living or a weekend escape in the country. This home has many upgrades and recent improvements. See the Partial List of Improvements in the Documents tab.

37143 Adams Green Ln, Middleburg

$1,445,000
4 Beds 4 Baths VALO2125854 MLS
Proudly presenting an exceptional property located in the Town of Middleburg, situated within walking distance to many ethnic restaurants, several world class museums, a plethora of unique boutiques and the renown, 5-star, Salamander Resort and Spa. This end-unit residence is in pristine condition and masterfully blends artistic design with 'Hunt Country' style. Enjoy private parking, a generous yard, no HOA and hi-speed internet! The French-influenced landscaping features impressive topiary urns, pea gravel trim, copper gutters, and solar lighting. The interior offers 11-foot ceilings, solid hardwood floors, and exquisite details including crystal chandeliers plus hand-carved newel posts. The upgraded kitchen boasts hardwood cabinets, an induction range, a soapstone farm sink, LG appliances and offers a generous eat-in area which can easily accommodating your guest. The primary suite includes a luxurious spa-inspired bathroom punctuated by an Arabesque-style marble floor, a jetted tub, marble shower, private toilet closet and cosmetic, fog-free mirrors. In addition to two, generous upper-level bedrooms sharing a dual vanity bathroom and a fourth floor spacious loft, this home offers a sunny bedroom and full bathroom on the main level too! A significant highlight is the "Showcase" lower level which features an impressive, fully equipped bar accented by Turkish marble flooring, a custom-designed iron railing, a camouflaged mechanical room, recessed lighting and a full bathroom. This soundproof space which includes an extensive waterproofing system is ideal for the ultimate in entertaining friends and family! The baby grand piano including the rug may be purchased separately. You can find additional information at the Town site: www.middleburgva.gov

12 Orange Dr, Middleburg

$2,700,000
3 Beds 3 Baths VALO2126254 MLS
Special home and property set in Virginia’s famed Hunt Country just west of Middleburg, this exceptional estate is the first property on the left in the sought-after Atoka Chase community. Enter through the private security gate and follow the tree-lined drive past the horse barn to a beautifully constructed Cape-style stone residence set on 18 fully fenced acres overlooking an amazing pond and manicured fenced pastures. Designed for both elegant country living and equestrian pursuits, the property features copper roofs and gutters on the house, cottage and garage, extensive landscaping and hardscaping, horse barn with heated office tack room, fenced paddocks, a machine barn, and thoughtfully designed outdoor spaces that capture the beauty of the surrounding Virginia countryside. The main residence offers three bedrooms and two-and-a-half baths with warm, timeless interiors and picturesque views from nearly every room. Sought after primary bedroom suite on the main level. The stone work was done by a local master craftsman in 1990. A separate guest house includes one bedroom and one full bath and half bath. All new SS appliances, redone kitchen and bathrooms, providing ideal accommodations for guests, extended family, or a farm manager. Propane heating for the main house and heat pump for the cottage. Additional amenities include an indoor heated spa/lap pool, oversized two-car garage, horse barn, and multiple outbuildings supporting both recreational and working farm use. Stone duck house building overlooking the pond with fountain. Multiple paddocks and 3 automatic waterers. This 18 acre gem combines privacy, beauty, and functionality, and this rare Atoka Chase offering presents an extraordinary opportunity to enjoy refined country living just minutes from historic Middleburg. Property has potential to build another home on the property per counsel opinion for the estate. Subject to the covenants in the Deed of Dedication dated October 20th, 1980 and the approval of the ARC.

34520 Atoka Chase Ln, Middleburg

$2,845,000
4 Beds 5 Baths VALO2124228 MLS
Back on the market through no fault of the home. Buyer financing fell through. Amazing opportunity. Move fast! Want to build a custom home near Middleburg, but not wait for new construction? Welcome to Affirmed Park Court …a stunning French transitional home located just minutes from downtown Middleburg in Banbury Cross Reserve, an exclusive enclave of custom homes. Offering over 6,000 square feet of beautifully finished living space, this home was thoughtfully designed for today’s discerning buyer and is move-in ready. The floor plan includes 4 bedrooms with ensuite baths, plus the flexibility for a 5th bedroom and bath on the lower level, ideal for guests or an in-law suite. Privately sited at the end of a cul-de-sac, the premium lot enjoys protected views of fields and woods under permanent open space easement. Stone gate posts and a paved driveway lead to the all-brick residence with a deep front porch, mahogany entry doors, and designer carriage lighting. Inside, wide-plank white oak floors, soaring 10’ ceilings, and extensive custom millwork set the tone. Highlights include a formal dining room, private office, living room with built-ins, wet bar, and a dramatic family room with coffered ceilings and a floor-to-ceiling stone fireplace. The gourmet kitchen features Omega cabinetry, quartz countertops, a 12’ island, and premium Sub-Zero, Wolf and Cove appliances. The kitchen opens to the light-filled breakfast room with doors to the rear deck, complete with a gas-plumbing for a grill and automatic awning for outdoor entertaining. Upstairs, the luxurious primary suite offers a sitting room, dual walk-in closets, and a spa-like bath with soaking tub and oversized shower. Three additional ensuite bedrooms, plus a well-appointed laundry room with double washers and dryers, complete the second floor. The unfinished lower level offers abundant potential for recreation, fitness, a guest space and storage. Residents enjoy walking the community roads and the protected open spaces and easy access to Route 50, Dulles International Airport, and Washington, DC. Please see documents section for the extensive list of upgrades and custom features.

23084 Affirmed Park Ct, Middleburg

$2,700,000
4 Beds 5 Baths VALO2124276 MLS
Canterwood presents a rare and compelling offering just moments from the heart of Middleburg—an exceptional 10.5-acre property that seamlessly blends refined living with a fully equipped equestrian lifestyle. The gracious home is thoughtfully sited to capture the beauty and tranquility of its surroundings. Inside, warm decor and hardwood floors, five fireplaces, and a notable elegant living room. The spacious kitchen flows easily into multiple indoor and outdoor gathering areas. The large finished lower level offers remarkable versatility, featuring a home office, recreation/media room with fireplace, bar, storage and an additional half bath. Outdoors, the property truly shines. Gorgeous, established gardens are complemented by stone walls, multiple patios and terraces—perfect for entertaining or quiet relaxation. The pool, peaceful pond with dock, and open land enhance the sense of retreat, while approximately two acres of woods add privacy and natural charm. Equestrian amenities are equally impressive: a four-stall stable with tack room, hayloft, and wash rack; 3 paddocks; two run-in sheds; and a bluestone riding ring. Additional features include a two-car garage, paved driveway, and high-speed Xfinity fiber internet. Canterwood is a rare opportunity to enjoy a peaceful, private lifestyle with close proximity to Middleburg’s shops, dining, and amenities—an ideal balance of elegance, comfort, and rural charm. Views to the east of the Bull Run Mountains. Live here, work here, swim her and ride here.

23559 Parsons Rd, Middleburg

$874,000
VALO2122142 MLS
Seize the opportunity to build your dream home in Middleburg, in the heart of Virginia wine and horse country! This is one of two beautiful lots available 7 acres each (available together for a total of 14 acres). Road frontage on Beaverdam Bridge Rd. This listing is for LOT #2, a beautiful wooded lot that provides privacy on a hill contiguous to LOT #1 which has an open field with rolling hills and a complete horse fence and tree surround. A few miles from downtown Middleburg with boutique shopping, fine dining, and renowned equestrian culture. Perfect for an equestrian farm or country estate with privacy on all sides and easy access to DC, Dulles Airport, and all Northern Virginia. Price is per lot. Custom builder and architect available if desired. Rare opportunity with very limited lots available in Middleburg.

20962 Beaverdam Bridge Rd, Middleburg

$849,000
VALO2124004 MLS
Seize the opportunity to build your dream home in Middleburg, in the heart of Virginia wine and horse country! This is one of two beautiful lots available 7 acres each (available together for a total of 14 acres). Road frontage on Beaverdam Bridge Rd. This listing is for LOT #1, a beautiful open field lot that has rolling hills and a complete horse fence and tree surround. This is contiguous to LOT #2 that is a wooded private lot on a hill. A few miles from downtown Middleburg with boutique shopping, fine dining, and renowned equestrian culture. Perfect for an equestrian farm or country estate with privacy on all sides and easy access to DC, Dulles Airport, and all Northern Virginia. Price is per lot. Custom builder and architect available if desired. Rare opportunity with very limited lots available in Middleburg.

20958 Beaverdam Bridge Rd, Middleburg

$2,695,000
5 Beds 5 Baths VALO2117342 MLS
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

$549,500
VALO2121980 MLS
Unique and rare land parcel available right in the heart of the historic village of Middleburg. This offering is for a raw land parcel in the rear of the lot. This parcel was divided into two independent parcels fully approved by the town. (Front lot has a ranch home that is currently being renovated). The rear parcel is open, private and level with a pipe stem driveway for easy access. Enjoy a short walk to downtown shops, restaurants, town pool, post office, grocery stores, library and more. Visit the Museum of Hounds and Hunting or the National Sporting Library & Museum. Walking trails at the nearby Salamander Resort and the campus of the Hill School are easily accessed. Minutes to local wineries, breweries and a cidery. Enjoy all the seasonal town events like the Farmers Market, Octoberfest, the 1000 Miglia car rally, Middleburg Film Festival and Christmas in Middleburg. Build a hunt-box or luxurious home tucked privately off Chestnut Street in the heart of Virginia horse country. Don’t miss this special opportunity! (See documents section).

LOT B - Chestnut St, Middleburg

$1,975,000
4 Beds 5 Baths VALO2120426 MLS
A truly enchanting 4-bedroom, 4.5-bath residence nestled in the heart of Middleburg, this beautifully crafted home—built in 2019 by a highly esteemed local builder—offers an exquisite blend of timeless elegance and modern luxury. Thoughtfully designed and impeccably maintained, the home is presented in flawless, turnkey condition with refined finishes at every turn. At its heart, the gourmet kitchen is a culinary showpiece, adorned with a generous center island and appointed with premier appliances including a Wolf range, Sub-Zero refrigerator, and Miele dishwasher. It flows effortlessly into a sunlit family room where a warm fireplace, soaring 9-foot ceilings, intricate millwork, and classic plantation shutters create an atmosphere of understated sophistication and comfort. Step outside to savor the charm of gracious outdoor living—whether relaxing on the welcoming front porch or entertaining on the private rear deck. A detached garage and tucked-away rear parking add both convenience and appeal, while high-speed internet ensures seamless modern living. Just a short stroll from Middleburg’s charming boutiques, fine dining, and vibrant village life, this exceptional property offers a rare opportunity to enjoy the romance of small-town living with every contemporary luxury at your fingertips.

105 Reed St, Middleburg

$9,000,000
VALO2119982 MLS
The opportunity of a lifetime has come to fall in love with and become the owner Cana Vineyards and Winery and Black Oak Cafe. Cana sits on 43+ picturesque acres with 8 acres under vine in Middleburg, VA. The offering includes all property, equipment and inventory. Black Oak Cafe opened in 2025, open on weekends to serve up dreamy gelato, pizza and espresso drinks. Cana has been a consistent winner of regional and international wine awards..190+ Awards..Virginia Winery of the Year..Loudoun County Winery of the Year..Winemaker of the Year..Virginia Governor’s Cup..Virginia Governor’s Case Gold..Best in Class, 7 Double Gold, 45 Gold, and 123 Silver Medals. The winery is open Thursday-Monday, Black Oak Cafe is open for the season on Saturdays and Sundays and weddings and other private events can be held every day. Reach out today to schedule a private tour!

38600 Little River Tpke Tpke, Middleburg

$2,850,000
4 Beds 7 Baths VALO2118900 MLS
Fox Hill Farm sits just over a mile east of historic Middleburg, offering a rare chance to own a beautifully remodeled estate that blends refined living with true Virginia equestrian charm. Set on 7.6 picturesque acres and reached via paved Four Chimneys Lane off Little River Turnpike, the property offers 6,547 finished square feet across the main residence and barn apartment. The elegant two-level brick home features a main-level primary suite with a spacious walk-in closet incorporating a second laundry, plus two additional bedrooms each with its own en-suite bath. A gracious foyer opens to formal living and dining rooms, while the expansive gourmet kitchen, anchored by a grand center island, flows into a bright breakfast area and light-filled great room with a striking Palladian window framing views of the paddocks and barn beyond. A side-loading two-car garage completes the main level. The recently finished lower level offers a home theater, recreation room, library/office, sitting room, full kitchen, wet bar, full hall bath, laundry, and two additional en-suite bedrooms, with walk-out access to a rear patio overlooking the landscaped grounds. A separate driveway serves the fully remodeled guest cottage and barn, currently operating as a short-term rental, complete with an oversized detached garage. Additional features include a fenced kitchen garden, outdoor gathering area, and potential for an accessory dwelling, subject to approvals. A truly special Middleburg retreat.

23333 Four Chimneys Ln, Middleburg

$1,289,990
VALO2116294 MLS
Build your new home on this incredible 12+ acre parcel that is located just off of rte 50. Less than 8 miles from Willowsford & less than 3 miles East of the historic village of Middleburg. This parcel offers close to 400 feet of road frontage.<br><br>There is no formal entrance to this parcel. Please park @ Sally Mill Rd that is across the parcel, LEFT side of the parcel (when facing the front of the subject parcel).<br><br>Seller has contacted VDOT last year. Application has not been made. Verbally on the phone VDOT mentioned to Seller that the driveway access to the subject parcel will most likely be from the RIGHT side of the parcel (when facing the front of the subject parcel). This proposed driveway to the parcel will most likely mimic the new construction home that is right across the subject parcel. Pls check the pictures to get an idea.<br><br>Within a short drive to many local wineries and historic towns. Ideal commuter location with easy access to Dulles International Airport and downtown Washington DC.

Lot 3 Little River Tpke, Middleburg

$325,000
PASY2002674 MLS
Prime High-Density R-4 Development Opportunity in the Borough of Middleburg! This offering includes approximately 10+ acres, fully serviced by public water, sewer, and stormwater infrastructure — a rare find for developers seeking scale and utility access. The property was previously engineered for a high-density residential concept, representing the maximum allowable unit count under current R-4 zoning. The site borders the Middleswarth Potato Chip facility and offers stunning elevated views from the top of the parcel — including scenic views overlooking town. Development flexibility allows a purchaser to maintain high density or reduce lot count for larger parcels, depending on vision and market strategy. Opportunities of this size with utilities, zoning support, and conceptual engineering in place are increasingly difficult to find. Sellers are experienced developers and licensed general contractors who are available to assist a buyer with land development, site work, and home construction under contract. Exceptional investment and development opportunity — bring your vision and unlock the potential.

Lot Furnace Rd, Middleburg

$1,550,000
3 Beds 3 Baths VALO2116974 MLS
Welcome to 22244 Sam Fred Rd, Middleburg, VA an Active Working Farm. Nestled in the heart of scenic Middleburg, this exceptional 18-acre equestrian property presents a rare opportunity to own a fully operational horse farm in one of Virginia’s most sought-after countryside settings. Offering privacy, open space, and endless potential, this working farm blends comfortable residential living with equestrian amenities. Whether utilized as a Boarding Farm, or maintained as a private farm your family will not be disappointed. The property suits trainers, students, horse owners needing boarding, or those seeking to expand an existing program. For your horses' comfort, the farm includes three barns with a total of 30 horse stalls including five broodmare stalls, three tack rooms, two feed rooms, and a lighted riding ring. This ranch-styled home features approximately 3,326 square feet of living space on two levels.  Two separate entrances afford your the opportunity to sit and enjoy the front porch or ease of access to the farm area. Thoughtfully designed to accommodate both everyday living and entertaining, the 1st level features three bedrooms and two bathrooms, a well-appointed kitchen, and a breakfast area that leads out to a large deck. The walkout basement includes a spacious living room filled with natural light, a welcoming family room, a bathroom, and a multifunctional bonus room ideal for an in-law suite, a home office, studio, or guest space.  For your personal use a detached two-car garage and ample paved parking exist. The property is being sold strictly as-is, in its current condition. A detailed brochure is available upon request. This is a rare opportunity to acquire a turnkey equestrian facility in prestigious Middleburg — where country lifestyle meets equestrian excellence. For the safety of everyone visiting and the animals, we ask that all visitors to the farm be escorted onto the premises. All visits to the farm are by appointment and escort only. Please do not wander or let children roam freely. For the safety of the animals no glass products are allowed on the farm.  Please park on paved surfaces only, no parking on grass surfaces.

22244 Sam Fred Rd, Middleburg

$449,900
2 Beds 1 Baths VALO2115404 MLS
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

$1,550,000
3 Beds 3 Baths VALO2116714 MLS
Welcome to 22244 Sam Fred Rd, Middleburg, VA an Active Working Farm. Nestled in the heart of scenic Middleburg, this exceptional 18-acre equestrian property presents a rare opportunity to own a fully operational horse farm in one of Virginia’s most sought-after countryside settings. Offering privacy, open space, and endless potential, this working farm blends comfortable residential living with equestrian amenities. Whether utilized as a Boarding Farm, or maintained as a private farm your family will not be disappointed. The property suits trainers, students, horse owners needing boarding, or those seeking to expand an existing program. For your horses' comfort, the farm includes three barns with a total of 30 horse stalls including five broodmare stalls, three tack rooms, two feed rooms, and a lighted riding ring. This ranch-styled home features approximately 3,326 square feet of living space on two levels.  Two separate entrances afford your the opportunity to sit and enjoy the front porch or ease of access to the farm area. Thoughtfully designed to accommodate both everyday living and entertaining, the 1st level features three bedrooms and two bathrooms, a well-appointed kitchen, and a breakfast area that leads out to a large deck. The walkout basement includes a spacious living room filled with natural light, a welcoming family room, a bathroom, and a multifunctional bonus room ideal for an in-law suite, a home office, studio, or guest space.  For your personal use a detached two-car garage and ample paved parking exist. The property is being sold strictly as-is, in its current condition. A detailed brochure is available upon request. This is a rare opportunity to acquire a turnkey equestrian facility in prestigious Middleburg — where country lifestyle meets equestrian excellence. For the safety of everyone visiting and the animals, we ask that all visitors to the farm be escorted onto the premises. All visits to the farm are by appointment and escort only. Please do not wander or let children roam freely. For the safety of the animals no glass products are allowed on the farm.  Please park on paved surfaces only, no parking on grass surfaces.

22244 Sam Fred Rd, Middleburg