Main Content

Upperville VA Homes For Sale

Your Guide To Upperville VA Homes For Sale

Instantly access Upperville Subdivisions/condo listings

Upperville, VA is west of and adjacent to Middleburg, VA located 46 miles Northwest of Washington, D.C. Founded in the late eighteenth century as Carrstown, Upperville was originally named after Josephus Carr the city’s first settler. Early in the nineteenth century, Carrstown was renamed Upperville, VA. The close proximity to Washington, D.C. and the availability of large tracts of land in Upperville, VA attracted some of the wealthiest and most successful titans of American industry.

Upperville, VA was a natural environment for the Sport of Kings: thoroughbred racing. One of the early more well-known Upperville, VA thoroughbred enthusiasts was Isabel Dodge Sloane, heiress to the Dodge automobile fortune. In 1929, Isabel purchased an 850 acre property in Upperville, VA, eventually leading her to becoming one of the country’s champion race horse breeders. She called her thoroughbred race horse breeding farm Brookmeade Stable. Paul Mellon, the son of Andrew Mellon, former US Secretary of the Treasury and co-heir of his grandfather, Thomas Mellon’s vast Mellon Bank fortune created their Upperville, VA thoroughbred race horse breeding farm called Rokeby Stables. Rokeby Stables established in Upperville, VA in 1948 won more than 1,000 stakes races. Bertram and Diana Firestone of the Firestone Tires Empire of Newstead Farm in Upperville, Virginia in 1982 became part of the Virginia Thoroughbred Association Hall of Fame.

As you can see, Upperville, VA has clearly made its mark in the thoroughbred racing world. And no wonder, perhaps, because the Upperville Colt and Horse Show, the oldest horse show in the county has been show casing their love of horses since 1853. Another Upperville, VA famous horse lover’s event is the Hunt Country Stable tour which since 1959 “offers visitors from around the globe a chance to experience the charm of Hunt Country life, as well as an opportunity to experience the sight and grandeur of some of the finest equestrian facilities known to the world.”

If you are interested in getting on a horse and learning Polo there is no better place to go than the Virginia International Polo Club of Upperville, VA. Polo is the oldest sport in the world going back 2000 years and Virginia International Polo Club is the very best at instructing the beginner to refining the skills of the accomplished Polo player.

Being a lover of nature but not so inclined to mount and ride for those that want to keep their feet on terra firma and not astride a horse then Historic Ayrshire Farms maybe the ticket. Ayrshire describes itself as a certified organic working farm, “specializing in rare and endangered breeds livestock and heirloom fruits and vegetables”. Ayrshire Farm has been around since the early 19th century and their Hunter’s Head Tavern restaurant is ready to serve your culinary appetite today.

If you are interested in a more scholarly experience, also available in Upperville, VA is the Oak Spring Garden Library which is a powerful celebration of the life of the late, Bunny Mellon, wife of the late, Paul Mellon. Bunny was a horticulturalist, a gardener, philanthropist, and art collector, her Oak Spring Garden Library is a “collection of over 16,000 objects, including rare books, manuscripts, and works of art dating back to the 14th century.”
Upperville, VA is a lovely window into our country’s past, present and future. Speaking of the future, “The former Blackthorne Inn, under new ownership by Easton Porter Group, is closed for full renovations and will reopen with a country resort concept and new name/branding in Spring 2019”. Assuredly, Upperville, VA is a remarkable city with wonderful homes and sprawling estates and is a fabulous place to visit or to call home.