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18 Upperville, VA Real Estate Listings

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New
Est. Payment$4,495,000
5 Beds | 8 Baths | 6,683 Sqft

33024 Sunken Ln, Upperville, VA 20184

House For Sale

Set on 86.81 gorgeous acres, the panoramic mountain views enjoyed from Oakfield's grounds are extraordinary (and secure thanks to the neighbor's land being in conservation easement). This exceptional property features a fully appointed 5 bedroom, 5 bath, 3 half bath, 3 fireplace manor house with a grand foyer (complete with a discrete elevator), gourmet kitchen, sumptuous master suite and a cozy pine-paneled den with a wet bar and fireplace. The house is supported by a full house generator along with a 4 stall horse barn with a ring, heated saltwater pool with pergola, and a recently renovated tenant house.

New
Est. Payment$1,849,500
4 Beds | 6 Baths | -- Sqft

1306 Greystone Rd, Upperville, VA 20184

House For Sale

This stunning Williamsburg brick colonial is ideally located on 52+acres with lush woodlands, brilliant gardens & spectacular mountain views. Constructed with extraordinary quality & beautiful detailing, this absolutely charming custom residence has been totally renovated in the past few years. It now boasts a new gourmet Kitchen, new HVAC , new Pella windows, new custom doors and Visual Custom lighting throughout the home. The Baths have all been remodeled and heated floors and towel bars installed in the "His and Hers" Master Baths. The roof has been replaced along with three front dormers, the cupola, well pump and well pressure tank, bringing everything to "turn key" and pristine condition. Wonderful high ceilings, gleaming wood floors, five fireplaces & a fabulous screened porch make this an extraordinary retreat for peace and tranquility. The main level is open and airy, and includes the Dining area and Library , all with access to the rear porch and brick terrace, It is perfect for gracious entertaining. Also located on the main level is the luxurious Master Suite, boasting a wood burning fireplace, walk-in closets and "His and Her Baths", flooding the rooms in natural sunlight. On the second level there are three additional Bedrooms and two updated tile baths.The land is exquisite, boasting flowering trees, extraordinary gardens and a stocked spring fed pond. Historic Upperville is just two miles away.

Cricket Bedford

Est. Payment$650,000
3 Beds | 3 Baths | 2,400 Sqft

1144 Delaplane Grade Rd, Upperville, VA 20184

House For Sale

Enjoy a weekend retreat or full-time residence on 2.4+ acres in the heart of the village of Upperville. This turn-key cottage blends old with new combining a 1919 log cabin with a wonderfully creative addition that is loaded with CHARM! Today's sought after floor plan is found in the spacious Kitchen that opens to the Family Room and Dining Room and features a cathedral ceiling with beams and painted floors. Lovely 1st floor Master Bedroom suite with a cathedral ceiling, lots of closets and a luxury Master Bath. Cozy Living Room is located in the original section of the house with exposed log walls. Just off the living room is a small home Office. There are two more Guest Bedrooms & 2 more Full Baths. Updated windows, well, septic (Advantex), roof, geo-thermal heating & cooling and large fenced back yard for pets. Walk to restaurants, churches & the Post Office. Don't miss!

Est. Payment$450,000
4 Beds | 3 Baths | 2,998 Sqft

9267 Patrick St, Upperville, VA 20184

House For Sale

The historic village of Upperville is located on John Mosby highway 50 miles to Washing to D.C, 11 miles to Route 66, 20 miles to INOVA Hospital, 32 miles from Washington Dulles International Airport, 9.9 miles to Sky Meadows State Park, and 7 miles to Middleburg. This inviting enclave offers a lifestyle centered in outdoor enjoyment, land preservation, education, and community. Equestrian events include: polo, steeple chase, horse showing, and fox hunting. With vineyards, state parks, shopping, and a five star Resort life in the country provides every amenity you desire. 9267 Patrick Street has mature trees, historic stone walls and a large yard. This brick cape cod is recently renovated and can be seen anytime. The front porch, back patio, beautiful hardwood and bamboo flooring, main level master, large bedrooms, fire places, and deluxe kitchen make it the perfect home. All bathrooms have tile to the ceiling and granite. Move in ready!

Est. Payment$2,775,000
5 Beds | 8 Baths | 7,374 Sqft

10000 Mount Airy Rd, Upperville, VA 20184

House For Sale

** View Virtual Tour: http://tour.homevisit.com/mls/270661 ** Extraordinary brick colonial on 50+ gorgeous acres in prestigious Greystone. Over 9,000 square feet of spectacular living space featuring 3 beautifully finished levels. Heated pool, tennis court and brilliant gardens overlook a picturesque pond with fabulous mountain views in a private location. In-person showings permitted.

Est. Payment$1,425,000
4 Beds | 4 Baths | 3,904 Sqft

10227 John S Mosby Hwy, Upperville, VA 20184

House For Sale

"Hillcrest", spectacular hilltop setting, bold mountain views and Paris valley views. Home updated in 2017, 4 bedrooms, 4 bathrooms, 3 fireplaces, gourmet kitchen, vaulted ceilings, skylights, lovely gardens, walkways and terrace. Improvements include in ground pool with spa, 2 stall barn with tack room, room for horses, spring fed pond. 13.37 acres next to parkland surrounded by large estates.

$5,000,000
Est. Payment$19,500,000
8 Beds | 6 Baths | 6,500 Sqft

1344 Rokeby, Upperville, VA 20185

House For Sale

HERONWOOD FARM AND GOLF COURSE- * 500 Acres of Perfection close to Washington, D.C. in the breathtakingly beautiful Upperville, Virginia Countryside. *GOLF- After trips to Scotland, the owners fell in love with the game of golf and chose to have their own Private 18 Hole Golf Course built to USGA Standards and offering 4 tees boxes per hole. Professionally engineered and meticulously maintained the Fairways, Greens and Ponds are perfectly sited for one to enjoy the serenity of the Blue Ridge Mountain views, providing the perfect escape from the stressful Washington, D. C. lifestyle. * HORSE FACILITIES - Adjacent to the Prestigious Upperville Horse Show Grounds, once part of this estate, Heronwood Farm is a magnificent Horse Property located in Prime Piedmont Hunt Territory. The Owners of Heronwood commissioned Blackburn Architects to design the 2 main stables which have been featured in Blackburn's Healthy Stables Book, as well as Leffingwell's Ultimate Horse Barns Book. Blackburn designed the Yearling Stable (8,250 sq. ft) center aisle with 16 (15' x 15') Stalls and Broodmare Stable (9,750 sq. ft.) center aisle with 20 (15' x 15') Stalls + 3 (15' x 15') Birthing Stalls; both barns are in pristine condition and feature continual ridge skylights and vertical ventilation providing exceptional light and fresh air. Additional equestrian facilities include: Polo Field, 120' x 220' outdoor arena, 8 horse Hot Walker, enclosed lunging pen, 3 isolation buildings, additional stalls, numerous run in sheds, 28 (4 board) fenced paddocks covering approximately 200 acres, 11 bay Service Center, miles of interior roads and stone walls. * HISTORIC GRAFTON MANOR HOUSE, c. 1903, with it's grand 42" wide entry door, 10' ceiling height, 8' high windows and plaster mouldings, was completely restored and redesigned by Blackburn Architects for staff housing into 4 (2 bedroom) Apartments and Farm Office. Additional Housing: Farm Manager's House, Staff House, and several Apartment

$350,000
Est. Payment$4,400,000
5 Beds | 5 Baths | 4,680 Sqft

20561 Trappe Rd, Upperville, VA 20184

House For Sale

**View Virtual Tour: http://tour.homevisit.com/mls/282260 ** Trappe Hill Farm is a serene 474 acre estate in 5 parcels. From its high elevation, on the eastern slope of the Blue Ridge mountains, this farm commands some of the most magnificent views in Loudoun County. Lovely residence with first floor master bedroom suite, handsome library, formal and informal dining, living/family room adjacent to kitchen and open to stone terrace. Three tenant houses, stable with 13 stalls, wash stall, office and 1 bedroom apartment. 4 bay machine shop. Fenced paddocks and fields with 11 run-in sheds. The property includes various easements.

$50,000
Est. Payment$1,575,000
4 Beds | 4 Baths | 2,750 Sqft

21562 Greengarden Rd, Upperville, VA 20184

House For Sale

BREATHTAKING VIEWS! ACREAGE & MORE ACREAGE! This Beautiful Property includes a Gorgeous Custom-Built Home Located in Wanted Open Space in Upperville's Hunt County; Precisely Located on 27 Acres with Amazing Full Views of the Blue Ridge Mountains for Stunning Sunsets. Open Concept Luxury Home with Single Level Living; Master Bedroom and Master Bathroom on Main Level Along with 2 Additional Bedrooms with a 4th Bedroom and Study located on the Loft Level, 3.5 Bathrooms, Large Kitchen, Dining Room, Foyer and Living Room with Fireplace; 2,750 Finished Living Space, with an Additional 2,000+ of Unfinished Basement Space with a Walk-Up Egress. Property Includes a 3 Car Side Loading Attached Garage, Beautiful Exterior Masonry with Stone Front, Hardiplank Siding; Extra Large Deck for Outdoor Living and Entertaining to Capture Beautiful Sunrises and Endless Open Space Views. Property is Generator Ready, Includes an Extra-Large Outdoor Building for Equipment, Storage and more~ This is a MUST SEE HOME and PROPERTY!!

Est. Payment$4,850,000
4 Beds | 5 Baths | 5,795 Sqft

1388 Crenshaw Rd, Upperville, VA 20184

House For Sale

Set on an idyllic five-acre parcel, bordering a 400 acre private estate, this extraordinary Neoclassical Palladian villa offers over 6,000 square feet of interior living space and spectacular views of the iconic Blue Ridge Mountains. Originally built in 1997 by esteemed architect Errol Adels, Sageview finished a two-year complete renovation in late 2017. Inside, a magnificent Great Room includes the gourmet kitchen, dining room and two seating areas that overlook the terrace and swimming pool. Each of the property's five bedrooms - including two large ground level master suites - offer ensuite baths clad in floor to ceiling Carrara marble. Additional noteworthy features include an indoor/outdoor Sonos sound system, 10' custom doors, custom oak cabinetry, Miele and Sub-Zero appliances, Italian marble countertops, Lefroy Brooks fixtures and sconces, reclaimed wide-plank flooring, and custom millwork throughout. The 1,225 sqft. guest house features a spacious entertaining space with a concealed full kitchen, large bedroom and ensuite bath.

Est. Payment$34,000,000
9 Beds | 11 Baths | 12,500 Sqft

21515 Trappe Rd, Upperville, VA 20184

House For Sale

Llangollen is not just a home, but rather a "place" in the broadest sense of the term. Steeped in historical significance, it is one of the largest privately owned "places" on the Department of the Interior's National Historical Registry. Much more than a place to live, it is a truly wonderful and magical place in time. Llangollen is a property without peer and offers a lifestyle like no other. Llangollen's establishment dates to 1795 standing witness to many great historical events, including being the site of the prelude to the1863 Battle of Gettysburg. Pristine yet functional, inviting yet cloistered, this astounding estate offers a serene setting of gently rolling terrain. The Manor House is sited proudly in the center of over 1100 acres of pastures, ponds, forest lands and attended to by all of the necessary structures and features of the grand estate it is today. While bearing the distinctive architectural features of its circa 1800 era, it has been updated with modern day enhancements.Enjoy the property as a delightful family retreat, filled with outdoor activities and connections with nature. Llangollen offers plenty of opportunities for equestrian pursuits including polo, thoroughbred-breeding and fox hunting as well as dairy farming or a vineyard. ***Please familiarize yourself with the array of buildings, barns and facilities situated throughout its grounds in the "documents" section of this listing.***Llanglollen looks forward to greeting its next steward and continuing on with its magnificent legacy.

$150,050
Est. Payment$999,950
4 Beds | 4 Baths | 4,000 Sqft

9075 John S Mosby Hwy, Upperville, VA 20184

House For Sale

The Academy, Historic Icon of Upperville w/ Georgian Style Main House steeped in Civil War & local history 2 - 2 Bay garages, & lush front & back gardens w/ mature trees. Renovated in 1998 by current owners who added a Sunroom & Kitchen as well as bringing original fixtures & hardwood floors back to life. Exquisite knot & rose garden with Gravel paths. Large-Livable Antique. The 2 bedroom income producing Guest Cottage was renovated in 2020 with new paint, porches, carpet, bathrooms and kitchen updates and is currently tenant occupied. Superb property that offers great flexibility with two dwellings and oversized yard with space for a pony..right in the heart of the Village.

$300,000
Est. Payment$4,125,000
4 Beds | 5 Baths | 4,000 Sqft

21167 Trappe Rd, Upperville, VA 20184

House For Sale

MAJOR PRICE REDUCTION. Gracious Lakeview on 166 prime acres w/ renovated & tasteful manor home,3BD Guest Cottage,9 stall Barn, Indoor Arena, Machine shed & fenced paddocks on private treelined entry drive w/ BlueRidgeMtns to West boundary & LAKE at foot of East boundary. Exquisite hardwood floors, updated Baths, Kitchen w/ SS stove, custom cabs & counters, lightfilled views. Private. Under 85 mins to DC.

$2,000,000
Est. Payment$13,000,000
4 Beds | 5 Baths | 4,000 Sqft

20854 Trappe Rd, Upperville, VA 20184

Farm For Sale

CLEREMONT FARM is a MAGNIFICENT 1511 ACRE ESTATE consisting of 3 Contiguous Farms, which can be sold separately: CLEREMONT (410 Acres in 5 parcels), BELLEFIELDS (422 Acres in 2 parcels) and ROSS (679 Acres in 2 parcels). CLEREMONT is an AWARD WINNING CATTLE FARM nationally known for it pristine water quality and sustainable grazing. ***POTENTIAL FOR A TURN KEY CATTLE OPERATION including CATTLE, MANAGEMENT and EQUIPMENT***LOCATED in Western Loudoun County, this Property offers forest and fields on the Eastern Slope and Piedmont of the Blue Ridge Mountains, 33 verdant pastures, wildlife habitat and 1000 Acres of Hardwood Forest, 400 of which are flatland timber managed on a 20-25 year rotation. Riding Trails, Hiking Trails, Beautifully Managed Fields and Ponds have created a Retreat with Tremendous Opportunities for Riding, Fishing, Hiking, Hunting and Bird Watching. In an area with Olympic riders, this land is adjacent to NEWSTEAD FARM and in the PIEDMONT HUNT TERRITORY. RESIDENCES include: Historic Manor House, c. 1820, Second Manor House, 3 Tenant Houses and Patent House, c.1760. OUTBUILDINGS INCLUDE: Farm Office, Garages, 14 Stall Barn, Machine Shop and Hay Barns. PRISTINE WATER from Natural Springs, including Jeffries Branch, 3 Ponds and Wetlands, is Protected by 4.5 Miles of Fencing. Water is Supplied to all Fields with Spring-fed or Energy-free Water Troughs piped from Existing Wells. 130 Acres of Riparian Buffers for Wildlife Habitat are Protected with Wildlife Friendly Fences. 2 MILES of Interior Roads Provide Access to Homes and Fields. WILDLIFE INCLUDE: Wild Turkey, Grouse, Dove, Fox, Deer, Bobcats, Geese, Duck, Black Bear and Bald Eagles.

$690,000
Est. Payment$3,300,000
266 Acres

9024 Quadrangle Rd, Upperville, VA 20184

Lots Land For Sale

266 acres in Piedmont Hunt.Panoramic views of the Blue Ridge, Bull Run & Cobbler mountains which surround the whole property Improvements include 4 farmhouses, an iconic red dairy barn and many agricultural buildings, ponds and traditional stone walls. This working farm is protected by a Virginia Outdoors Foundation conservation easement which allows 2 parcels. Formerly property of Mellon Family

$176,000
Est. Payment$1,175,000
93.77 Acres

Greengarden Road, Upperville, VA 20184

Lots Land For Sale

No conservation easement or restrictions. Open 94-acre Upperville parcel surrounded by pristine estates and equestrian properties. Views of Blue Ridge Mountains. An amazing opportunity to build in a desirable location. Indoor arena permissible.

$750,000
Est. Payment$4,200,000
141.35 Acres

21712 Willisville Rd, Upperville, VA 20184

Lots Land For Sale

An incredible opportunity to own a fabulous farm in Upperville, boasting almost 141 acres of open pastures and magnificent woodlands in the heart of the Piedmont Hunt Territory. The land includes a charming 3 bedroom stone house, nestled in the woods and a four stall barn in the adjacent paddock. This wonderful parcel would be ideal for easement potential & benefit from excellent tax credits.

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