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A Little History

Hillsboro was originally known simply as “The Gap”, named after the Gap in Short Hill Mountain where it’s located.   Later it became “Hillsborough” when it was formally established in 1802.  At that time, the population was about 100 residents.  During this time it became a busy commercial area with several Mills located on  Catoctin Creek, multiple general stores, blacksmiths, tanneries, tailors and three taverns!  It wasn’t until it was incorporated in 1880  that it officially became simply “Hillsboro”.   Today, Hillsboro is a little more relaxed, and most of those shops and taverns are now residences, and in fact the population today is only slight larger than it was in 1802, now with 107 residents according to the 2024 census!!

Hillsboro Historical Homes

During the pandemic, Hillsboro went under a major $30M revitalization project and Route 9 was actually closed through Hillsboro while they transformed Hillsboro with gorgeous sidewalks, underground utilities, lighting and roundabouts making downtown a safer, walkable location… even on busy Route 9. 

Area Attractions & Amenities

“Hillsborough” is far from forgotten.  In fact, Hillsborough Winery & Brewery still uses the original spelling today!  “The Gap” creates amazing views, and Hillsborough Winery refers to those views as Ruby Sunsets, perfect for drinking a glass of Red Wine and enjoying the remainder of the day, often with a live acoustic musician on a Friday or Saturday evening. 

On the other side of Hillsboro, you’ll find Harvest Gap Brewery, a working farm that serves craft beers, local food, and has music on the weekends ranging from solo musicians to full bands!   Love the photo with the fire pit and "The Gap" in the background!

Hillsboro is surrounded by wineries and breweries.  Just north, heading along Mountain Road towards Lovettsville, is Doukenie Winery.  And if you follow Hillsboro Road to the south towards Purcellville, you’ll find Old 690 Brewery, Hillsboro’s oldest brewery, and Walsh Family Wine, which sponsors the wine at one of my favorite events, Polo in the Park!

Head west past Hillsborough Winery and you’ll come across places like Breaux Vineyards (a popular spot that features music and festivals on the weekends), and 868 Estate Vineyards (home of LocoFest, a local music festival,check out my video coverage!!!)

The town itself has regular events held at the Old Stone School.  They regularly have old fashioned "hoe downs" and square dancing, and in the summer months, on Friday nights, they host "Music in the Gap", which is a music series featuring local musicians such as the Short Hill Mountain Boys, the Talton Brothers, and Hard Swimmin Fish!  They also host the Appalachian Trail Festival and have their own Fourth of July fireworks display!

And while Purcellville, with all it’s shopping and dining, is just a five mile drive away down Hillsboro Road, you also have Charlestown, WV about ten miles away to the west!  If you aren’t familiar with Charlestown, it’s a “hot spot” for activities and nightlife.  And while Charlestown has a ton of history to explore, you’ll also find dozens of eateries and shops. 


But, we have to call out the Hollywood Casino and Race Track, which in addition to gambling (if that’s your thing), also brings big entertainment to the area, with a diverse range of bands like Los Lobos, The Little River Band, Bare Naked Ladies and… yes, even Michael Bolton (if that’s what you’re into!! LOL).  They also draw comedians like Dave Attel, Pete Davidson, Kathleen Madigan and more. 


Hillsboro gives you that middle of nowhere feeling, but you’re not far from civilization when you want it!

Hillsboro nearby attractions

The Homes:  The Old & The New

Hillsboro itself has some beautiful old homes.  But, as you can imagine with such a small town, there is rarely inventory here.  If you own a home here and are thinking of selling, give me a call, I’d love to represent you!  At Sotheby’s we have lists of buyers looking for historic properties!  If you’re thinking of buying here, your best bet is to contact me so I can setup an automated search for you.

Here’s an example of a 3,100 square foot, four bedroom home, that sold in late 2023 for $775K.  Built in 1833, this home has all the charm you’d expect from an early 19th century home, but with updated kitchens and appliances. 

You can also find some “newer” homes, like this home that sold for $1.25M...  Okay, 1903 might not be “new”.  😊  And truthfully, it will be difficult to find something like Stonehedge Farm unless you are truly patient.  On almost 10 acres, the property has multiple buildings including the 4 bedroom farmhouse and a pre-Civil War stone barn and spring house!

Something a Little Newer

Truthfully, there are not a lot of “planned communities” nearby.  But, as you head West on Route 9 towards West Virginia, about a mile outside of town you’ll come across places like Winding Creek (17 homes), Salem Farms (29 homes) and Saratoga (54 homes). 


Homes in these developments are typically on just over an acre of land, with 3,500-6,000 square feet of living space, with sales in the last few years ranging from $650K up to just over $1M. 

Here’s an example of one of the larger homes, at 6,100 square feet, that sold in late 2023 for $985K

Heading south towards Purcellville, you’ll find Longmoor Farm Estates with 33 homes, and to the east you’ll find places like Catoctin Creeks with 55 homes.  Both of these communities feature large homes ranging in size from 6,000-10,000 square feet, hitting price tags over $2M.   Here’s an example of a 7,100 square foot home on 12 acres of land that sold for $1.9M.  Absolutely stunning with amazing views in the middle of rural Loudoun County.  If open space AND luxury are on your requirements list, this is the place for you!

As I mentioned, Hillboro Rd takes you to Purcellville, but if you take the road less traveled and leave out of Hillsboro via Stony Point Rd towards Round Hill, you’ll find some beautiful communities such as The Highlands with 96 homes.  It’s aptly named “The Highlands", given that it goes way up on the ridge line backing to the Appalachian Trail even! 

Homes in The Highlands are typically between 4500-6500 square feet, on an acre or more of land, with price tags starting just over a million dollars.  Technically, these homes have a Round Hill address, and take advantage of some of the amenities offered at the town of Round Hill.  But, they are roughly halfway between Round Hill and Hillsboro, separated by “The Gap” in Short Hill Mountain range.  

Here’s an example of a home that sold here for just over a million dollars with 6,700 square feet of living space and 6 bedrooms on 3 acres of land.  In the overhead shot, you can tell it’s on a “hill”, but I have actually biked up that hill, and it’s one of the toughest climbs in the area!  The photos don't do it justice!!!!

And you’ll find a handful of other small communities throughout the area also.  Places like Dunthorpe Farms (18 homes), Birch Hollow Hamlet (23 homes), Milligans Run (15 homes), Jonella Farm (33 homes), and Ashby Farm Estates (20 homes).    

Hillsboro neighborhood Map

As a 20+ year Loudoun resident I know this area well, and I know how to maximize the value of your property and highlight the region to buyers.  I’d love to put all my knowledge, resources and energy to work for you!  So, if you are thinking about buying or selling in any of these amazing neighborhoods, give me a call!

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