Living in Middleburg, VA | Community Info | Long & Foster

Living in Middleburg, VA

The town of Middleburg, Virginia, was established in 1787, shortly after the Revolutionary War, and still maintains its small-town and close-knit community vibe. It was known first as Chinn's Crossroads, but was then named Powell Town after the Revolutionary War officer who first established the settlement. At Powell's humble request, the name was changed again, and the town eventually became Middleburg.

Middleburg History

Though a small town, Middleburg has seen its share of history. It was the site of two small battles during the Civil War and is the home of the Red Fox Inn, a building that dates from 1728. Additionally, the town center dates back to the 1800s and is on the National Register of Historic Places.

In the early 20th century, Middleburg, Virginia, was known as the place for steeple chasing and fox hunting, and drew spectators and participants from all over the nation. Residents today are still passionate about horse racing, and there are a number of tack exchanges, farm stores, and stables all around town. In the early 1960s, Jacqueline Kennedy was often seen in the Middleburg social scene, and she and President Kennedy built a residence just outside of Middleburg, but were only able to visit it once before he was assassinated.

Culture and Entertainment in Middleburg

If you're looking for a place that's full of tradition and history, you should consider buying a home in Middleburg. The historic Red Fox Inn is still in business today, both as a bed-and-breakfast and as a restaurant

The town offers several vineyards, distilleries, and cider mills that are enjoyed by locals, as well as historical museums and libraries, like the National Sporting Library & Museum. Antique stores are something many Middleburg homeowners enjoy, as are local bakeries. Celebrities like Tom Cruise, Paul Newman and others have stayed in Middleburg; Liz Taylor actually lived in Middleburg in the 1970s. Residents never know who they'll be rubbing elbows with next!

Middleburg Housing Options

There are a variety of housing options available for those looking at homes for sale in Middleburg. These range from town homes to small single-family homes or large country estates on many acres. The styles of homes in Middleburg, Virginia, range from historic buildings dating to the 19th century to brand-new homes with ultramodern architecture. Whether you're looking for a Victorian mansion, a new wood home, or a single-family brick ranch, you can find both the Middleburg neighborhood and house that fits your exact needs.

Nearby Cities

Your new home in Middleburg will place you within 50 miles of both Frederick, Maryland and Washington, D.C., which are both great destinations for a nightly or weekend visit if residents want to see a lot more history and enjoy several cultural and artistic destinations, not to mention the endless amounts of wonderful restaurants and fine dining in and around our nation's capital. With access to these big cities, Middleburg real estate is a sure bet for those looking to have the best in country life with history and tradition, while still accessing urban amenities.


Getting There & Around


What Locals Love

Don't Miss It

  • It’s all about rustic, country-style living for residents of Middleburg. Horse racing and shows reign supreme with numerous tack exchanges, farm stores, and stables found all around town.
  • The historic Red Fox Inn, established in 1728, has been graced by the presence of Elizabeth Taylor and Jacqueline Kennedy. Today, the inn operates as both a bed and breakfast and a restaurant.
  • Located in the midst of Virginia Wine Country, there are plenty of wineries, cider mills, and distilleries to spend a lazy weekend afternoon searching for your next favorite red or white wine.


Middleburg Real Estate at a Glance

  • 10 Homes Sold*
  • 121 Avg. Days on Market*
  • $2,550,000 Median Price*

*over last 3 months

Find Your Home in Middleburg

There Are 38 Properties Available in Middleburg



Interested in Middleburg?

Talk to an expert on Middleburg real estate.

Communities Near Middleburg

Sort by: