Upperville Homes for Sale

Upperville Homes for Sale

Welcome to Upperville, Virginia – a hidden gem nestled in the heart of the picturesque Virginia countryside. Known for its stunning landscapes and rich equestrian heritage, Upperville offers a unique blend of rural charm and modern convenience. This quaint town is surrounded by rolling hills, lush pastures, and scenic vineyards, providing an idyllic backdrop for those seeking a peaceful retreat from the hustle and bustle of city life.

Upperville is steeped in history, with roots dating back to the 18th century. The town retains its historic charm, featuring beautifully preserved architecture and a close-knit community that prides itself on its welcoming atmosphere. Residents enjoy a slower pace of life, with opportunities for outdoor activities such as horseback riding, hiking, and exploring the nearby wineries and farms.

For those considering making Upperville their home, you’ll be delighted to discover a variety of homes for sale that cater to diverse tastes and lifestyles. From charming historic properties with unique character to modern estates with expansive views, there’s something for everyone. Many homes boast large lots, allowing for ample outdoor space to enjoy the natural beauty that surrounds you. Whether you’re looking for a cozy cottage or a sprawling equestrian estate, Upperville's real estate market has options that will capture your heart.

With its breathtaking scenery, rich cultural heritage, and a tight-knit community, Upperville is more than just a place to live – it’s a lifestyle. Come explore the homes for sale and discover the enchanting allure of Upperville, where your dream home awaits!

Newest Upperville Homes for Sale

$899,000
3 Beds ⋅ 2 Baths
The simple pleasures of farmhouse living, in the heart of Upperville.<br><br> 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.<br><br> 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.<br><br> 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.<br><br> 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.<br><br> 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.<br><br> 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.<br><br> 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.<br><br> High Mountain Broadband installed.

1150 Poplar Row Ln, Upperville

Listing courtesy of Keller Williams Realty. Contact: 7034309008
$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: 7033788810
$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: 5406876321
$2,595,000
4 Beds ⋅ 4 Baths
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. All buildings are currently tenant occupied and require 24 hours' notice to show. No drive-ins.

33195 Millville Rd, Upperville

Listing courtesy of Thomas and Talbot Estate Properties, Inc.. Contact: 5406876500
$11,200,000
4 Beds ⋅ 4 Baths
BACK ON THE MARKET DUE TO NO FAULT OF THE SELLER OR PROPERTY. Peace and Plenty at Bollingbrook, circa 1809, presents an outstanding property in the history of Virginia. Originally part of a 9,600-acre land patent from Lord Fairfax in 1731 it later became a wedding present of 790 acres in 1809 whereas the one-story, Federal brick house of four rooms was constructed. Later in 1830, Robert Bolling added 21 rooms creating an ornate and classic Jeffersonian design with 15 ft. ceilings, beautiful fireplace mantels, intricate cornices and columns, a glorious staircase, beautiful hand-blown glass windows, decorative door handles and hinges and gorgeous, white oak floors. All original seventeen (17) structures remain: The Manor House, The Pool House, The Guest Cottage, The Gate House, The Chapel, The Overseer's House, The 12-stall Barn, The Old Silo barn (oldest in the State of Virginia), The Cannery, The Scale House, The Blacksmith Shop, A Wood Shed, The Schoolhouse, A Smokehouse, A Summer Kitchen, A Barn Apartment and The Hilleary House. The main house offers four generous entertaining rooms upon entry; a Music room, Living room, Meeting room and a Library. The expansive Dining room can accommodate two dozen friends and family. A Primary Suite with adjoining sitting room, opens to the deck sunroom and a stroll on the wrap around balcony. Of course, a luxurious bath leading to an expansive closet of 27 ft. x 18ft. outfits the suite. In addition, there are two, luxurious bedrooms with fireplaces and private baths, a back staircase, full basement, a three-car garage, and a lovely mudroom entry to the Kitchen with enclosed porch. The Pool House flanks a saltwater pool with a wide lounging ledge and overlooks the Blue Ridge displaying spectacular sunset views! Among the pristinely manicured grounds is the notable 250-year-old Cedar of Lebanon tree, largest in Virginia. Preserved in Easement with the Land Trust of Virginia and in the Piedmont Hunt territory, this 365-acre retreat offers unparalleled tranquility and privacy for All to enjoy!

1610 Delaplane Grade Rd, Upperville

Listing courtesy of Hunt Country Sotheby's International Realty. Contact: (540) 687-8500
$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: 5406876500
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