Upperville VA Real Estate & Homes for Sale

Tucked away on a quiet dead-end street on the southern edge of historic Upperville is this beautifully updated contemporary brick home offering the best of country living - peaceful, private and within walking distance to village favorites like Hunter's Head Tavern and the Market at Bluewater Kitchen. Set on 1.8 open acres, this thoughtfully renovated home features an open main-level layout ideal for modern living. The living and dining areas flow seamlessly into a bright, eat-in kitchen with a new oversized island, quartz countertops, LVT flooring and updated lighting. Also on the main level are the primary bedroom suite, a guest bedroom and a stylishly renovated full bath. The lower level is designed for comfort and versatility. It includes a cozy family room with a wood-burning fireplace, two additional bedrooms (one currently used as a fitness room), a second updated full bath and a dedicated home office complete with custom built-ins and a wet bar. The laundry/mudroom includes a new built-in custom cubby area and ample storage with direct access to the detached garage. Outdoor living is just as special: a fenced-in pool with a charming pool house (shower + half bath), two open decks, a covered front porch, and sweeping views of neighboring farmland and open lawn. An oversized two-car brick garage and a separate storage shed provide additional functionality. The property is partially fenced and offers ample room to relax and entertain. Just minutes to Route 50, this home is perfectly located for commuters yet feels worlds away. Live in the heart of Upperville, but with privacy and space. A must-see! (Separate lot available together with this parcel. See MLS#:VAFQ2016798).

Tucked away on a quiet side street in the heart of historic Upperville, the delightful Hatcher's Cottage has been thoughtfully and thoroughly renovated offering the rustic charm of hunt country with the comfort and style of today. Set on nearly half an acre, this picture-perfect property welcomes you with stepping-stones that lead to a handsome antique door adorned with a brass fox knocker. Inside, refined yet inviting spaces unfold which ideal for quiet moments or lively gatherings. The formal living room features gleaming hardwood floors, while the open gourmet kitchen impresses with top-of-the-line appliances, new cabinets and countertops, and views into the sun-drenched dining room. A wall of windows here frames a beautiful view of the gardens and sparkling pool below. Two bedrooms and two all-new full baths complete the main level. From the sunroom, step outside to the pool, or take the interior staircase to a bright and spacious lower level. Downstairs, you'll find a cozy family room with fireplace, a private home office, large laundry/mudroom, a third guest bedroom, and an additional full bath. A charming garden room complete with exposed stone walls, two greenhouse-style windows and French doors allow easy access to the pool area. The distinctive octagon-shaped pool features slender entry steps and an underwater bench all surrounded by an expansive pool deck perfect for lounging and entertaining. The fenced garden area includes a stylish new pool house with a full bath, sitting room and a private deck on one side. On the other side is the detached two-car garage with extra storage both above and behind. Improvements include new metal roof, new HVAC + mini-split system, updated septic, upgraded electric, new privacy fencing, fresh gravel on the driveway and buried fiber internet. A rare turnkey offering in one of Virginia's most picturesque villages - don't miss it!

Rare village offering with acreage and views! Tucked away on a quiet dead-end street on the southern edge of historic Upperville, this beautifully updated brick home offers the best of country living - peaceful, private, and within walking distance to village favorites like Hunter's Head Tavern and the Market at Bluewater Kitchen. Set on 1.8 acres and offered with an adjacent 2+ acre buildable parcel, this is a unique opportunity for expanded living or future investment. Thoughtfully renovated, this split-foyer home features an open main-level layout ideal for modern living. The living and dining areas flow seamlessly into a bright, eat-in kitchen with a new oversized island, quartz countertops, LVT flooring and updated lighting. Also on the main level are the primary bedroom suite, a guest bedroom, and a stylishly renovated full bath. The lower level is designed for comfort and versatility. It includes a cozy family room with a wood-burning fireplace, two additional bedrooms (one currently used as a fitness room), a second updated full bath, and a dedicated home office complete with custom built-ins and wet bar. The laundry/mudroom includes a new built-in cubby area and ample storage with direct access to the detached garage. Outdoor living is just as special: a fenced-in pool with a charming pool house (shower + half bath), two open decks, a covered front porch, and sweeping views of neighboring protected farmland and open lawn. An oversized two-car brick garage and a separate storage shed provide additional functionality. The property is fully fenced and offers ample room to relax, entertain, or explore future possibilities. Just minutes to Route 50, this home is perfectly located for commuters yet feels worlds away. Live in the heart of Upperville, but with privacy, space, and the bonus of an extra lot. A must-see!

Hidden behind a privet hedge, adjacent to the village of Upperville, Alston House ( 1129 and 1131 Delaplane Grade Rd) offers privacy and gracious living on two level lots. The main house was built in 1832 with an addition in 2002. It is approximately 6000 square feet on three levels, including 5 bedrooms and 4 1/2 baths. The pool house across the lawn on the second lot was in built in 2006. It is 3000+ square feet with a central great room which includes a kitchen and large pantry. On either side are two bedroom wings each with separate bathrooms. The pool house is used by the current owner as an art studio. The architectural integrity of the original historic house has been maintained while the 2002 addition accommodates more contemporary tastes. Sited on 2+ acres, the grounds include extensive mature boxwood, beautiful gardens and landscaping and a fishpond with a waterfall. The property is fully fenced. Alston House is a secret oasis of natural charm just outside the village of Upperville. The current owner has completed many upgrades and updates. See features list in the Document section. Please note the property consists of 2 tax parcels (6054-75-7394 & 6054-75-9340.)

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.

Gorgeous mountain views and ultimate privacy await you at this beautifully remodeled farmhouse-style retreat. Nestled on 10 peaceful, wooded acres, this home offers a serene escape while remaining just minutes from Sky Meadows State Park, local breweries, and vineyards. Currently operating as a successful Airbnb, the property presents a flexible opportunity - whether you're seeking a private getaway, an income-producing investment, or a home designed for entertaining. With no HOA and surrounded by mature trees, you'll enjoy both seclusion and freedom. The location is ideal, situated just 2.5 miles from the Upperville Colt & Horse Show and 4.5 miles from the Middleburg Classic, with easy access to Middleburg, Delaplane, Bluemont, and major highways. Inside, the open-concept layout invites you into a stunning kitchen outfitted with granite countertops, stainless steel appliances, a spacious island, and a double oven - perfect for cooking and entertaining with ease. Two expansive owner's suites, each with its own private en-suite bath, offer luxurious comfort and flexibility. A charming built-in shelving unit paired with a bay window creates a cozy space to relax and take in the views. The screened-in porch, complete with a stone fireplace, allows you to enjoy the beauty of every season in comfort. With four bedrooms, four and a half bathrooms, and a layout designed for entertaining both indoors and out, this home offers the perfect blend of modern amenities and rustic charm. Completely updated and equipped with HughesNet internet, staying connected is never an issue. The home can be sold fully furnished for an additional cost, making it truly turnkey. This is a rare gem in Virginia horse and wine country - don't miss your chance to own a slice of paradise. Please close the red gate after you enter the road. It was originally 10155 John S Mosby (road sign is being replaced by county)

Landmark 1,100? acre estate in the heart of the Middleburg/Upperville hunt country. Steeped in history, Llangollen dates to 1795 and is anchored by a gorgeous 9-bedroom Colonial Revival house. Sited at the end of a mile long driveway, the house features sweeping 180-degree views over the property and surrounding landscape. Extensive improvements include 8 tenant cottages, numerous outbuildings, and 8 ponds, among others. Equestrian resources include a best-in-class polo facility, 7 barns, and expansive turnout options. 700? acres of mostly level open ground, and 400? acres of forested land. Phenomenal scenery and privacy, yet only 1 hr to Washington, D.C. and 15 minutes to Middleburg. Under conservation easement, contact broker for details. Llangollen is a true generational asset in one of Virginia?s most iconic landscapes.