Upperville Real Estate

Set amidst the rolling landscapes of Virginia’s storied horse and hunt country, 1325 Rokeby Road presents a rare opportunity to experience the timeless elegance of the Upperville countryside. Privately situated on approximately 5 acres and surrounded by expansive estate properties and Fauquier County’s protected agricultural landscape, this classic Cape Cod-style residence offers an exceptional sense of peace, privacy, and place. Framed by the Blue Ridge foothills, the property enjoys sweeping scenic views and a beautifully appointed outdoor setting centered around a private pool with commanding mountain vistas. The residence reflects a quintessential Old Virginia aesthetic, paired with a generous and versatile floor plan designed for both gracious entertaining and comfortable everyday living. With 4 bedrooms and 3½ baths, the home offers abundant finished living space and a flexible configuration well suited to a variety of lifestyles. Outside, meticulously maintained landscaping, extensive hardscape, and thoughtfully designed gardens create an effortless connection between the residence and its natural surroundings. Every element of the grounds has been carefully considered, resulting in a turn-key exterior that is as inviting as it is refined. Located just off Rokeby Road in the heart of one of Virginia’s most sought-after historic equestrian regions, the property embodies the enduring appeal of the Upperville countryside: privacy, open land, magnificent scenery, and an unmistakable sense of Old Virginia character. A distinctive country residence in an extraordinary setting, 1325 Rokeby Road offers a rare blend of classic architecture, sophisticated outdoor living, and the enduring beauty of Virginia’s horse and hunt country.

1325 Rokeby Rd, Upperville

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

$875,000

3 Beds ⋅ 2 Baths

The simple pleasures of farmhouse living, in the heart of Upperville. There is something wonderfully comforting about an old farmhouse—the wide-plank feel of hardwood floors beneath your feet, rooms that feel connected rather than formal, sunlight moving through the windows, and the sense that generations have lived, gathered, cooked, and celebrated here. 1150 Poplar Row Lane captures that feeling beautifully, tucked along a quiet private street in the historic village of Upperville. Set on a full acre, this charming antique farmhouse offers three bedrooms and two full baths, with an easy, inviting floor plan designed for the way people actually live. The main level includes a living room, dining room, kitchen, sunroom, and the practical spaces that make a farmhouse work so well—a mudroom/pantry and laundry just off the kitchen. The kitchen is very much at the heart of the home, connecting everyday life with the dining and living spaces. The sunroom adds another layer of charm—a place to enjoy a morning cup of coffee, curl up with a book, bring in garden flowers, or simply watch the seasons change. Upstairs, three bedrooms and a large full bath offer comfortable private quarters, with hardwood floors throughout adding warmth and continuity to the home. Outside is where the farmhouse lifestyle truly comes to life. The one-acre setting provides room for gardens, outdoor gatherings, and the simple pleasures of having space around you. A large stone patio creates a natural gathering place for long summer dinners and evenings with friends, while the screened gazebo offers a shady retreat for lemonade, conversation, or an afternoon nap. A large shed provides plenty of room for gardening equipment and outdoor necessities, and the carriage house adds both character and wonderful potential. But perhaps the most appealing feature is the setting. This is not a farmhouse isolated miles from anywhere—it is farmhouse living within the beloved village of Upperville. Historic homes, mature trees, quiet streets, and the traditions of this remarkable Virginia village surround you, while Middleburg, wineries, farms, and the broader beauty of the Piedmont are close by. There is no pretense here—just the appeal of an old house with soul, a generous piece of land, and room to live a little more slowly. Grow a garden. Gather around the dining table. Spend summer evenings on the stone patio. Tuck away in the gazebo with a good book. Enjoy the changing seasons from the sunroom. And at the end of the day, come home to a house that feels as though it has always belonged here. 1150 Poplar Row Lane is a rare opportunity to embrace the charm, character, and everyday pleasures of an antique Virginia farmhouse—right in the heart of Upperville. High Mountain Broadband installed.

1150 Poplar Row Ln, Upperville

Listing courtesy of Keller Williams Realty. Contact:

$1,550,000

3 Beds ⋅ 2 Baths

European-Inspired Architectural Gem in Virginia Horse Country! Just eight miles from Middleburg and approximately one hour from Washington, DC, this exceptional 3,800-square-foot residence is a rare architectural gem, blending European-inspired elegance, exceptional craftsmanship, and modern luxury in the heart of Virginia Horse Country. Ideally located along John S. Mosby Highway just off Route 50, with the Blue Ridge Mountains as a scenic backdrop, the property is steps from Hunters Head Tavern and minutes from some of Virginia's most celebrated horse-country destinations, wineries, farm-to-table restaurants, and charming country inns. The location offers an extraordinary rural lifestyle while remaining conveniently accessible to Washington, DC. Designed in the style of a stately French cottage, thehas been thoughtfully and extensively reimagined by its current owners, with meticulous attention to architectural detail throughout. The approach is introduced by a new brick-paver driveway, slate accents, natural stone columns, and a slate walkway leading to an elegant copper-roofed entrance with custom cedar detailing. A newly constructed garage is distinguished by a custom all-wood barn-style door that complements the home's European country aesthetic along with maintenance free commercial grade epoxy flooring.Professionally landscaped grounds surround expansive slate patios, creating inviting outdoor spaces for al fresco dining, entertaining, or simply enjoying the peaceful surroundings and seasonal gardens. Inside, the completely renovated kitchen combines European-inspired design with modern functionality. Custom European cabinetry complemented by extensive wall tiles,premium quartz countertops, custom floating wood shelving, upgraded lighting, custom bench seating with storage, a new farmhouse sink and faucets, and premium JennAir stainless-steel appliances—including a cooktop, oven, oversized refrigerator/freezer, dishwasher, and wine cooler—create an exceptional culinary and gathering space. The adjoining dining room/library/study provides an intimate setting centered around a gas fireplace with an imported French mantel and custom built-ins. A dramatic black-and-white marble hallway leads into the grand living room, where hand-laid parquet flooring, expansive windows, patio access, electronic blinds, architectural artwork niches, and a nearly walk-in-sized gas fireplace create an elegant yet inviting environment for entertaining. Both fireplaces were professionally serviced in 2025. The main-level bedroom suite offers a private retreat with custom storage and a spa-inspired bathroom featuring a Japanese soaking tub, teak cabinetry, custom tilework, a floor-to-ceiling window, and a glass-enclosed shower. A custom-designed handrail introduces the upper level, where the home's flexible living spaces continue. The spacious primary bedroom features generous proportions and comfortable sitting areas, while an additional generously sized bedroom can easily serve as a home office, guest suite, or creative space. The upper level also includes an entertainment area, custom closets, thoughtfully designed storage, a combination of parquet and new barnwood flooring, and a beautifully appointed full bathroom with dual sinks, custom cabinetry, additional storage, a separate shower, and a modern soaking tub. Two independently controlled Bryant HVAC systems, installed in 2022, provide climate control for the main and upper levels and can also be remotely controlled. Recent improvements include a new commercial-grade 50-gallon water heater and new well water pump, both installed in 2026. Fiber-optic connectivity throughout the residence provides high-speed internet access for today's connected lifestyle. A truly distinctive property where French-inspired architecture, refined craftsmanship, and the timeless beauty of Virginia Hunt Country come together—just minutes from Middleburg and within easy reach of Washington, DC.

9016 John S Mosby Hwy, Upperville

Listing courtesy of Samson Properties. Contact:

$849,000

3 Beds ⋅ 3 Baths

Nestled in the heart of historic Upperville, this charming farmhouse offers timeless character on a picturesque 1-acre lot. Featuring 3 bedrooms, 2.5 bathrooms, and over 2,400 square feet of living space, the home welcomes you with a classic covered front porch, metal roof, and mature landscaping. A standout feature is the CV (Commercial Village) zoning, presenting a unique opportunity for buyers seeking a live/work lifestyle, boutique business potential, or future flexibility (buyers should verify permitted uses with Fauquier County). Enjoy the charm of village living while remaining just minutes from wineries, equestrian facilities, local shops, and commuter routes. Whether you're searching for a primary residence, weekend retreat, or property with business potential, this Upperville gem offers a rare combination of character, location, and opportunity.

9027 John S Mosby Hwy, Upperville

Listing courtesy of Corcoran McEnearney. Contact:

$2,125,000

4 Beds ⋅ 4 Baths

New price - a significant price repositioning! Small Spring Farm is being offered for the first time in over 50 years. Nestled on 27 scenic acres just north of Upperville, this charming horse property enjoys beautiful Blue Ridge Mountain views and offers a rare combination of history, character, and equine amenities in the heart of Virginia's hunt country. At the center of the farm is a unique residence created by linking two historic stone cottages, one dating back to 1812. The result is a warm and inviting home that can function as a single residence or as two connected living spaces, each with its own kitchen, making it ideal for extended family, guests, or a variety of living arrangements. Together, the home offers four bedrooms, four full baths, original hardwood floors, three fireplaces and numerous spaces for gathering and entertaining. Outdoor living is equally appealing, with a covered front porch, side porches, and a spacious rear deck overlooking the surrounding countryside and capturing spectacular sunset views. Equine facilities include a six-stall center-aisle barn with hayloft, five fenced paddocks, a round pen, riding ring and a large run-in shed. A detached equipment building provides multiple storage bays, a garage, and a charming one-bedroom, one-bath studio apartment with its own private garden. Protected by a VOF conservation easement and located within Piedmont Hunt territory, Small Spring Farm offers the privacy, beauty, and rural character that make this area so sought after. Don't miss!

33195 Millville Rd, Upperville

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

$10,950,000

4 Beds ⋅ 4 Baths

Peace and Plenty at Bollingbrook, circa 1809, is a remarkable Virginia estate with breathtaking sunset views and a history reaching back to the earliest years of the Commonwealth. The property was originally part of a 9,600-acre land patent granted by Lord Fairfax in 1731. In 1809, 790 acres were given as a wedding present, upon which the original one-story Federal brick house was constructed. In 1830, Robert Bolling expanded the residence to 21 rooms, creating the handsome Jeffersonian house that remains today, distinguished by 14-foot ceilings, finely carved fireplace mantels, intricate cornices and columns, a graceful staircase, hand-blown glass walk-through windows, original decorative hardware and white oak floors. The estate retains all 17 of its historic structures, creating an unusually complete record of life on a Virginia country estate: the Manor House (4BR/3.5BA), Pool House (2BR/1.5BA), Stone Guest Cottage (1BR/1BA), Gate House Cottage (1BR/1BA), Chapel, Estate Manager’s House (2BR/2.5BA), 12-stall Barn, Broodmare Barn, Underground Silo—the oldest in the State of Virginia, the Cannery, Scale House, Blacksmith Shop, Wood Shed, Schoolhouse, Smokehouse, Summer Kitchen, Barn Apartment (2BR/1BA), and the Hilleary House. This amazing property could serve as a multi-generational compound, thriving equine business, showplace for entertaining, private luxury escape or all of the above. The first-floor of the Manor House opens to a grand foyer and four magnificent entertaining rooms—a Music Room, Living Room, Meeting Room, and Library. Beyond is an expansive Dining Room suited to large gatherings. The second-floor hallway leads to the Primary Suite which includes an adjoining sitting room that opens to the sunroom and wraparound upper balcony. The primary bath leads to an exceptional 27-by-18-foot closet and dressing room. There are two additional bedrooms, each with a fireplace and private bath. A wrought-iron spiral staircases lead to a cupola with spectacular 360-degree views. The Manor House also includes a back staircase, full basement, three-car garage, and mudroom entry adjoining the kitchen and enclosed porch. The Pool House overlooks the saltwater, heated pool surrounded by French cast iron statues and long views of the Blue Ridge, particularly beautiful at sunset. Across the grounds are open lawns, historic outbuildings, horse pastures and fields, and magnificent mature trees including the notable 250-year-old Cedar of Lebanon, recognized as one of the largest in Virginia. Preserved in easement with the Land Trust of Virginia and within the Piedmont Hunt territory, the 365-acre Bollingbrook estate remains a rare example of a Virginia estate preserved in both character and setting.

1610 Delaplane Grade Rd, Upperville

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

$10,950,000

4 Beds ⋅ 4 Baths

Peace and Plenty at Bollingbrook, circa 1809, is a remarkable Virginia estate with breathtaking sunset views and a history reaching back to the earliest years of the Commonwealth. The property was originally part of a 9,600-acre land patent granted by Lord Fairfax in 1731. In 1809, 790 acres were given as a wedding present, upon which the original one-story Federal brick house was constructed. In 1830, Robert Bolling expanded the residence to 21 rooms, creating the handsome Jeffersonian house that remains today, distinguished by 14-foot ceilings, finely carved fireplace mantels, intricate cornices and columns, a graceful staircase, hand-blown glass walk-through windows, original decorative hardware and white oak floors. The estate retains all 17 of its historic structures, creating an unusually complete record of life on a Virginia country estate: the Manor House (4BR/3.5BA), Pool House (2BR/1.5BA), Stone Guest Cottage (1BR/1BA), Gate House Cottage (1BR/1BA), Chapel, Estate Manager’s House (2BR/2.5BA), 12-stall Barn, Broodmare Barn, Underground Silo—the oldest in the State of Virginia, the Cannery, Scale House, Blacksmith Shop, Wood Shed, Schoolhouse, Smokehouse, Summer Kitchen, Barn Apartment (2BR/1BA), and the Hilleary House. This amazing property could serve as a multi-generational compound, thriving equine business, showplace for entertaining, private luxury escape or all of the above. The first-floor of the Manor House opens to a grand foyer and four magnificent entertaining rooms—a Music Room, Living Room, Meeting Room, and Library. Beyond is an expansive Dining Room suited to large gatherings. The second-floor hallway leads to the Primary Suite which includes an adjoining sitting room that opens to the sunroom and wraparound upper balcony. The primary bath leads to an exceptional 27-by-18-foot closet and dressing room. There are two additional bedrooms, each with a fireplace and private bath. A wrought-iron spiral staircases lead to a cupola with spectacular 360-degree views. The Manor House also includes a back staircase, full basement, three-car garage, and mudroom entry adjoining the kitchen and enclosed porch. The Pool House overlooks the saltwater, heated pool surrounded by French cast iron statues and long views of the Blue Ridge, particularly beautiful at sunset. Across the grounds are open lawns, historic outbuildings, horse pastures and fields, and magnificent mature trees including the notable 250-year-old Cedar of Lebanon, recognized as one of the largest in Virginia. Preserved in easement with the Land Trust of Virginia and within the Piedmont Hunt territory, the 365-acre Bollingbrook estate remains a rare example of a Virginia estate preserved in both character and setting.

1610 Delaplane Grade Rd, Upperville

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

$2,575,000

4 Beds ⋅ 3 Baths

Welcome to Slate Hill, an exquisite country estate on almost 7+/- acres. Fully renovated interior and exterior in 2021 with all original features retained, including wide heart pine flooring throughout and detailed woodwork. This elegant c. 1700’s property has 4 bedrooms, 2.5 full baths and combines a wonderful mix of old and new. The property was originally a portion of the 2,000 acre land patent granted to George Washington by Lord Fairfax in 1768. The original house and cabin structures date from 1770s with additions to the house built in the 1820s. A stone entrance bridge with stone pillars crosses a small spring-fed stream, flanked by ancient boxwoods and wrought iron gates. A large parking area and driveway provides ease of access. Towering trees ring the property, providing a sense of your this beautifully private glen. The perfect country lifestyle awaits inside the house. A gourmet kitchen offers soapstone counters, custom cabinetry, farmhouse sink, imported AGA appliances and a casual dining area. The formal dining room retains its exposed original stone walls, restored beams, original fireplace and antique lighting. Living Room has expansive windows allowing the natural light to flood in, 9ft ceiling beams, and the original fireplace mantle. The master bedroom has a fireplace, cedar closets and a luxury bath with custom slate shower walls and Hansgrohe Raindance showerhead and fittings. Of the three guest bedrooms, one includes an en-suite bathroom and two walk-in wardrobes. Other features include new standing seam metal roofs on the main house and cabin, a new two-zone HVAC system, and a new washing machine and dryer (2024). A large stone patio is reached through the kithcen. Extensive mature landscaping and gardens surround the house. George Washington's original log cabin has been fully restored with a repointed chimney & two fireplaces, a loft bedroom and new full bath. Horse amenities include a center aisle barn by renowned builders King Construction (2021), with four oversized stalls, tack room, bathroom, wash stall and feed/laundry room. A breezeway with carriage doors provides beautiful airflow and views. Behind the barn, are four fenced paddocks and a 120x70 EquiSand riding arena that suits all riding disciplines.

10157 John S Mosby Hwy, Upperville

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

Upperville Real Estate

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