Upperville Real Estate

Upperville Real Estate

Welcome to Upperville, Virginia—a hidden gem nestled in the heart of Loudoun County, where the charm of rural living meets the sophistication of Virginia's horse country. With its picturesque landscapes, historic architecture, and close-knit community, Upperville offers a serene escape while being conveniently located just a short drive from the bustling cities of Washington, D.C., and Winchester.

Upperville is renowned for its stunning countryside, characterized by rolling hills, lush pastures, and scenic views that change beautifully with the seasons. The area is a haven for equestrian enthusiasts, boasting numerous farms and riding trails that make it a premier destination for horse lovers. The annual Upperville Colt & Horse Show, one of the oldest horse shows in the nation, draws participants and spectators alike, celebrating the rich equestrian culture that defines this charming town.

In addition to its equestrian heritage, Upperville offers a delightful blend of local shops, art galleries, and gourmet eateries, creating a vibrant community atmosphere. Residents enjoy a slower pace of life, with opportunities for outdoor activities such as hiking, biking, and exploring the nearby Appalachian Trail.

Families will appreciate the excellent schools and community programs available, fostering a nurturing environment for children to grow and thrive. Whether you're seeking a peaceful retreat or a place to build lasting memories, Upperville promises a lifestyle steeped in tradition, beauty, and warmth. Discover your dream home in this enchanting Virginia town, where every day feels like a retreat.

Newest Listings in Upperville

$498,800
3 Beds ⋅ 1 Baths ⋅ VALO2131154 MLS
Welcome to 33960 Welbourne Rd a beautifully updated and well-appointed stucco and stacked stone cottage nestled in the heart of Virginia’s renowned Hunt Country. Offering a rare combination of immediate livability and exceptional future potential. Zoned AR-2 with access to on-site sewer, it provides a unique opportunity for expanded or additional building without the typical drain field limitations. Featuring three bedrooms and one full bath, along with a detached two-car garage and a conditioned outdoor studio/workspace, ideal for a home office, creative pursuits, or fitness. Perfectly situated just minutes from the Upperville Colt & Horse Show Grounds, approximately 12 minutes to Middleburg, and 18 minutes to Purcellville, this property delivers both convenience and the timeless appeal of country living. Agent Partial Owner

33960 Welbourne Rd, Upperville
$899,000
3 Beds ⋅ 3 Baths ⋅ VAFQ2022772 MLS
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
$925,000
3 Beds ⋅ 2 Baths ⋅ VAFQ2022412 MLS
Price Reduced ----- Tucked away on a private lane in the heart of Virginia’s renowned horse country, this charming circa-1840 farmhouse offers the perfect blend of historic character and modern comfort. Thoughtfully updated while preserving its timeless farmhouse charm, the home features 3 bedrooms , 1 with a fireplace, 2 full updated baths, central air conditioning, hardwoods throughout, original kitchen cabinetry, rich architectural details, and two wood burning fireplaces. <br><br> Set on a picturesque 1-acre lot, the property includes an original carriage house adding to its historic appeal and offering endless possibilities for storage, workshop space, or future use.The property includes a new screened gazebo and storage shed. Surrounded by the beauty of the Upperville countryside, the setting provides privacy and tranquility while remaining conveniently located just off John Mosby Hwy, (Route 50).<br><br> Sun-filled living spaces, period details, and charm of a bygone era make this a rare opportunity to own a piece of Virginia history. Whether as a full-time residence, weekend retreat, or horse country escape, this charming farmhouse captures the essence of country living in one of Virginia’s most sought-after equestrian communities. <br><br> High Mountain Broadband installed.

1150 Poplar Row, Upperville
$2,595,000
4 Beds ⋅ 4 Baths ⋅ VALO2124578 MLS
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
$2,625,000
4 Beds ⋅ 3 Baths ⋅ VAFQ2016372 MLS
Welcome to Slate Hill, an exquisite country estate on almost 10 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
Start Your Search