Upperville Homes for Sale

Upperville Homes for Sale

Welcome to Upperville, Virginia—a hidden gem nestled in the heart of Loudoun County. Known for its picturesque landscapes and rich equestrian heritage, Upperville is a charming small town that offers a perfect blend of rural tranquility and modern conveniences. With rolling hills, lush pastures, and historic architecture, it’s no wonder that Upperville attracts those seeking a peaceful retreat from the hustle and bustle of city life.

The town is steeped in history, with roots dating back to the 18th century. Stroll through the quaint streets and you’ll discover beautifully preserved homes that reflect the area’s storied past. Upperville is also home to a vibrant community that celebrates its agricultural roots, hosting events such as the Upperville Colt & Horse Show—the oldest horse show in America—drawing equestrian enthusiasts from near and far.

For those considering a move to this idyllic locale, you’ll be pleased to find a variety of homes for sale that cater to diverse tastes and lifestyles. Whether you’re looking for a charming cottage, a spacious family home, or an expansive estate, Upperville offers a range of properties that showcase the area’s natural beauty. Many homes feature stunning views of the countryside, expansive gardens, and easy access to outdoor activities like horseback riding and hiking.

Living in Upperville means embracing a lifestyle that values community, nature, and tradition. With its welcoming atmosphere and stunning surroundings, it’s the perfect place to call home. Explore the available homes for sale today and discover your dream residence in this enchanting Virginia town!

Newest Upperville Homes for Sale

$899,000
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
$925,000
3 Beds ⋅ 2 Baths
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

Listing courtesy of Keller Williams Realty. Contact: 7034309008
$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
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
$2,625,000
4 Beds ⋅ 3 Baths
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

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