Uncover Middleburg's Past

For over two centuries, Middleburg has preserved everything about its historic lifestyle, from its brick sidewalks and storefronts to the countryside itself. Discover Middleburg's rich history and why so many people call this community home.


More Than 200 Years of History

The town that we love today was established in 1787 by a Revolutionary War officer named Leven Powell. As the centuries passed, this town soon developed into a bustling coach stop and commercial center.

With its ideal location on Ashby's Gap Turnpike, Middleburg turned into a popular overnight destination for weary travelers. The name "Middleburg" itself stems from its location in the middle of lower Loudoun County and upper Fauquier County (especially between Alexandria and Winchester). Not surprisingly, Middleburg became more than a stop along a trade route.


Explore Historic Middleburg

Today, Middleburg's iconic city grid and street names (including Washington, Constitution, and Madison) pay homage to Middleburg's local culture and national influence. Eager to experience Middleburg's history and Hunt Country charm firsthand? Allow us to introduce you to this wonderful area!


group of equestrians at a fox hunt

Local Hunts

Spurred by the locally famous Grafton-Middlesex Foxhound Match in 1905, which took place in the Middleburg area over a period of 12 days, several hunts were established in the early 1900s. The Loudoun Hunt was originally established in 1894, and The Middleburg Hunt was established in 1906.

dinner plate at a historic inn

Historic Inns

Stone and brick buildings from the late 1700s to early 1900s are still standing proudly along the city streets. Inside these historic properties, you'll find well-established inns like the Red Fox Inn & Tavern (built in 1728) and the Windsor House Inn (built in 1803) still providing accommodations for travelers.

boutique clothing store

Modern Amenities

Town ordinances ensure that Middleburg will maintain its rural, historic charm. Modern shops and offices in Middleburg are set up in historic buildings rather than new properties, giving the town an old-fashioned feel. Be sure to stop by some of these local businesses!


Own a Piece of History in Middleburg

The Middleburg Historic District was listed on the National Register of Historic Places in the early 1980s, and there have been great efforts to preserve the historic streets and businesses. Throughout most of the city, and especially on Marshall Street and the eastern end of the town, you'll find that Middleburg has remained the same for virtually two centuries.

In such a historic area like Middleburg, it's not uncommon to find homes and farms that were constructed well before the 1900s. Browse the listings below to find all historic properties available on the local real estate market.

Historic Properties for Sale in Middleburg

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Contact Horse Farms & Country Homes

The town of Middleburg is a community that's proud of its history and local equestrian culture. If you have any questions about what it's like to live in Middleburg, or if you're considering buying a home in our area, contact us at 703.966.9480.

© 2019 Bright MLS. The information provided is for consumers, personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified.


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