Middleburg (and Upperville)
A Little History
Sitting on the southern border of Loudoun County, next to Fauquier County, Middleburg was originally called “Chinn’s Crossroads”, and was officially established in 1787. Middleburg was named so because it’s the halfway point between Alexandria and Winchester along Route 50!
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But, starting in the early 1900s it became known for its fox hunts and steeplechase horse racing. It quickly earned the reputation as the “Nation’s Horse & Hunt Capital”! This heritage is still on display today, most prominently during the town’s annual Christmas Parade where dozens of horses and hounds make their way through town.
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In this video you can see our Middleburg Office behind the riders!
The Lifestyle & Amenities
Glenwood Park is still host to three large horse events, the Middleburg Spring Races, the Point to Point races, and the Fall Races. And you’ll find one of America’s oldest horse shows at the neighboring town of Upperville (just west of Middleburg), the Upperville Colt & Horse Show!
They also play host to the Middleburg Film Festival here! Middleburg may be a small town, but this four day Film Festival attracts BIG stars and movies! In 2023, they featured Oscar nominated movies as “American Fiction” (starring Jeffrey Wright), “Anatomy of a Fall” (Canne’s Film Festival Palme D’or winner), The Holdovers (Paul Giamatti), Saltburn (Barry Keoghan & Margo Robbie), Nyad (Annette Bening & Jodie Foster), “Zone of Interest” (Canne’s Grand Prix winner) and many others. The event draws in major actors, directors and producers from around the world!
They also play host to the Middleburg Film Festival here! Middleburg may be a small town, but this four day Film Festival attracts BIG stars and movies! In 2023, they featured Oscar nominated movies as “American Fiction” (starring Jeffrey Wright), “Anatomy of a Fall” (Canne’s Film Festival Palme D’or winner), The Holdovers (Paul Giamatti), Saltburn (Barry Keoghan & Margo Robbie), Nyad (Annette Bening & Jodie Foster), “Zone of Interest” (Canne’s Grand Prix winner) and many others. The event draws in major actors, directors and producers from around the world!
And in the center of town you’ll find the Middleburg Community Center. In the summer they have a Friday night concert series, and a sports and swimming camp for the area youth (ages 3-12). They also have Holiday parties, plays and concerts and many other events throughout the year!
And, being in Western Loudoun, you are surrounded here by wineries and breweries like Cana Vineyards, 50 West Vineyards to the east, & Lost Barrel Brewing to the west, all of which have Live Music on the weekends too!
And we have to mention that Middleburg is host to one of the most exclusive resorts in Western Loudoun County, Salamander Resort & Spa. People come from around the region to spend the weekend at this luxury resort, featuring multiple indoor and outdoor pools, equestrian facilities, tennis & pickleball, zip lining, and even clay shooting and falconry! And if you’re up for 18 holes of golf, they have an exclusive arrangement with the Club at Creighton Farms, a private gated golf course community just north along Route 15 towards Leesburg.
And while Salamander has its own great restaurant, Harrimans Grill, the town itself has dozens of boutique shops and restaurants to choose from also. As you enter town, you’ll come upon Tremelo Bar, specializing in “elevated but unpretentious drinks and small bites”.
Just down the road is The Red Fox Inn & Tavern, established in 1728!!! With 22 rooms, it’s an amazing place to stay and experience a little history. But, like all good Taverns, they’ve got a great restaurant, The Night Fox Pub!
And across the street you’ll find the King Street Oyster Bar. You might be asking, “King Street”? And you’d be correct. The original King Street Oyster Bar is in downtown Leesburg! It was so successful, they opened a second restaurant here in Middleburg! It’s definitely a hot spot!
And there are a ton of other great restaurants like Red Bar Sushi & Thai Kitchen, Bluewater Cocina (Bangin tacos, margaritas & more!), and Red Horse Tavern with live music Friay & Saturday nights til midnight!
The Homes & Neighborhoods
Middleburg is in the “Little River” District of Loudoun County, and unlike many of the other sections of the county, the area has not been developed nearly as much. You can see from this map of Loudoun Home Owner Associations, that the Little River district (lower left corner) is mostly undeveloped.
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But, if you look inside the town limits, you’ll find plenty of gorgeous homes, not part of any HOA, giving you walking access to the town. And, while you can certainly find older homes going back to the early 1900s, you’ll also find new homes here as well! This home was built in 2019 and recently sold for $1.7M only a few blocks from the center of town!!
Looking outside of town, on the northeast side of Middleburg you have the brand new neighborhood of Banbury Cross Reserve which is still being developed, and eventually will have 38 homes each on 3-4 acres with prices starting at just over $2M. Currently (2024), only a handful of homes have been built, so if you’re looking to build your dream home in this area, this might be the place for you! If you are thinking of buying here, give me a call. While you don’t “need” a Realtor to buy new homes, you “should” still use one! It’s no cost to you, and I can not only save you money, but I can double check the developers work and make sure you get what you pay for!
On the south side of town you also have the neighborhood of Melmore with about 30 homes. Most homes are around 4,000 square feet. Here’s an example of a recent sale for $1.3M with 4,400 square feet on over 3 acres.
Middleburg Downs, on the west side of town, features 42 homes, mostly built in the 70s and 80s. You’ll find a wide variety of homes and lot sizes here from just over 2,000 square feet to over 5,000 square feet, typically on 3 acres or more. Here’s an example of a 5000 square foot home for sale here in 2024 for just over $1.1M on just under 4 acres built in 1975.
If you go farther west you’ll find Atoka Chase, another small but beautiful neighborhood with about 23 homes, all on 3+ acres. This is a great example of a 4900 square foot home that recently sold here for just over $2M with 11 acres, a pond and a barn!
But, venture farther out and you are in true horse country where you can find large estates and farms if you are patient (and have a great Realtor to help you!!). This 15,000 square foot estate on over a hundred acres of land sold in 2024 for $7.8M!!!
Or how about this historic home built in 1816 on 138 acres that sold for $4M! Truly owning a piece of history!
I specialize in luxury in this area. If you are thinking of buying or selling here, give me a call. As one of Loudoun’s top producing Realtors, I know how to maximize your home sale and get you top dollar for your home. Give me a call… I’d love to put all my knowledge, energy and resources to work for you!