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Upperville, VA Homes For Sale

Upperville is an unincorporated community Fauquier County and very near the Loudoun County line.

Established in 1790 as Carrstown, it was renamed to Uppervilel after an act passed by the Virginia General Assembly in 1819. It is a historical landmark designated by National Register of Historic Places.

Browse current Upperville, VA Homes For Sale. Can't find a home that fits your needs? Try our Advanced Loudoun County MLS search. You can easily filter properties by location, price, amenities, and more to find exactly what you're looking for.

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About Upperville, VA Real Estate

Upperville's home stock consist almost exclusively of single-family homes.

Most homes available are priced $1 million and above, although there are a few homes that can be bought from $600,000 to $900,000.

Almost all homes have an at least an acre of land. 

 

Living in Upperville, VA

Wineries, Vineyards, and Horses - that's what Upperville and it's surrounding area is known for.

It is a charming rural town that shares a border with both Fauquier County and Loudoun County. Residents get to enjoy the vast landscapes and an idyllic environment.

Situated along US route 50, it allows residents plenty of options to explore other towns, including Downtown DC, which is just 1 and a quarter of hour away.

 

 

 

 

 

 

21167 Trappe   Road, Upperville image
21167 Trappe Road, Upperville $3,950,000

Absolutely stunning manor home with 4 bedrooms, 3 full bathrooms, and 3 half bathrooms with a beautiful lake view on 166 lush acres. This light-filled home features expos...

  • 4 Beds
  • 6 Baths
  • VALO422830 MLS
21000 Trappe   Road, Upperville image
21000 Trappe Road, Upperville $4,500,000

WINDSOR FARM with its 115 Acres is an extraordinary horse property complete with lush pastures, stables, and training facilities. Located minutes from Upperville in the ...

  • 7 Beds
  • 6 Baths
  • VALO419104 MLS
9009 John S Mosby, Upperville image
9009 John S Mosby, Upperville $4,500,000 ▼

Deerfield Farm - 181 acres situated on the eastern edge of the historic village of Upperville. Stately brick manor house, ca. 1844 has manicured lawn and gardens once fe...

  • 8 Beds
  • 7 Baths
  • VAFQ165812 MLS
9009 John S Mosby   Highway, Upperville image
9009 John S Mosby Highway, Upperville $4,500,000 ▼

Deerfield Farm - 181 acres situated on the eastern edge of the Historic Village of Upperville. Stately brick manor house c. 1844 has manicured lawn and gardens once fe...

  • 4 Beds
  • 4 Baths
  • VAFQ165804 MLS
1344 Rokeby, Upperville image
1344 Rokeby, Upperville $19,500,000 ▼

HERONWOOD FARM AND 18 HOLE PERSONAL GOLF COURSE- * 500 Acres of Perfection close to Washington, D.C. in the breathtakingly beautiful Upperville, Virginia Countryside. *...

  • 8 Beds
  • 6 Baths
  • VAFQ164352 MLS
1388 Crenshaw   Road, Upperville image
1388 Crenshaw Road, Upperville $4,350,000 ▼

Set on an idyllic five-acre parcel, bordering a 400 acre private estate, this extraordinary Neoclassical Palladian villa offers nearly 6,000 square feet of interior livin...

  • 5 Beds
  • 7 Baths
  • VAFQ162658 MLS
21515 Trappe   Road, Upperville image
21515 Trappe Road, Upperville $29,000,000 ▼

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 "place...

  • 9 Beds
  • 11 Baths
  • VALO393148 MLS
21515 Trappe   Road, Upperville image
21515 Trappe Road, Upperville $29,000,000 ▼

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 "place...

  • 9 Beds
  • 11 Baths
  • VALO391446 MLS
21562 Greengarden   Road, Upperville image
21562 Greengarden Road, Upperville $1,475,000 ▼

BRAND NEW PRICE!!! | BREATHTAKING VIEWS! ACREAGE & MORE ACREAGE! This Beautiful Property includes a Gorgeous Custom-Built Home Located in Wanted Open Space in Uppervill...

  • 4 Beds
  • 4 Baths
  • VALO329208 MLS
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