Loudoun County
Hillsboro, Virginia
Loudoun's smallest incorporated town: a single stone street in a Blue Ridge gap on Route 9, with a few dozen buildings and a restored old school at its center.
Hillsboro is Loudoun County’s smallest incorporated town: about a hundred residents, one street, and a few dozen 18th and 19th-century stone and frame buildings in a gap through Short Hill.
The town
Charles Town Pike — Route 9 — is the street, and the town. At its center the restored Old Stone School serves as a community and events space and is the focus of most of what happens here. The town has its own mayor, council, and town tax on top of Loudoun County taxes.
Living on a through road
The honest characteristic of Hillsboro is that its one street is a through route between Loudoun County and West Virginia. Traffic, including heavy vehicles, passes close to the houses. The town has pursued streetscape and traffic-calming work to address it.
Anyone considering a house here should stand outside it at rush hour before making an offer. It is the single thing that decides whether this village works for a given buyer.
Around it
The wooded slopes either side of the gap hold mountain lots and larger parcels; Hillsboro Road runs south toward Purcellville and Round Hill; Route 671 heads east toward the Between the Hills country. All on wells and septic systems, with the usual steep-ground constraints on drainfield siting.
Schools
Loudoun County Public Schools, generally the Woodgrove High School pyramid. Confirm the current attendance area for a specific address with LCPS.
Getting around
Route 9 east to Purcellville and Route 7 in about ten minutes, west over the Blue Ridge into West Virginia. Leesburg roughly twenty-five minutes east.
For a Washington commute, the workable option is MARC or Amtrak from Harpers Ferry, a short drive northwest across the state line — worth checking schedules and parking before relying on it.
Buying or selling here
There is no useful average in a market this size; each sale is its own event, and inventory appears rarely enough that patience is the main requirement. Buyers should test the road noise, check what historic review applies to exterior work, and confirm the well and septic. Sellers should expect a buyer who wants Hillsboro specifically — and should be candid about Route 9, because it will come up either way.
Communities in Hillsboro
- Charles Town Pike
- The town's one street — Route 9 through the gap — lined with 18th and 19th-century stone and frame buildings.
- Old Stone School
- The restored school building at the center of town, now a community and events space.
- Short Hill and the gap
- Wooded slopes rising either side of the town, with mountain lots and larger parcels.
- Hillsboro Road south
- The road toward Purcellville and Round Hill, with farms and scattered houses.
- Route 671 and Woodgrove edge
- The countryside east toward the high school and the Between the Hills area.
Schools
Loudoun County Public Schools serves the town and the surrounding area, generally through the Woodgrove High School pyramid. Confirm the current attendance area for a specific address with LCPS.
Commuting
Route 9 runs through the town, east to Purcellville and Route 7 in about ten minutes and west over the Blue Ridge into West Virginia. Leesburg is roughly twenty-five minutes east. There is no rail or bus service; Charles Town and Harpers Ferry are close, and Harpers Ferry has MARC and Amtrak service toward Washington.
Market
Hillsboro is the smallest market in Loudoun County — a few dozen buildings, a handful of sales in a decade — surrounded by mountain land and countryside on wells and septic systems. In-town buildings are 18th and 19th-century stone and frame, and exterior work is subject to historic review. There is no useful average here; every transaction is specific. Buyers are choosing a very particular place, and inventory appears rarely enough that patience is the main requirement.
Common questions
How small is Hillsboro?
Around a hundred residents, which makes it Loudoun County's smallest incorporated town. It is essentially one street — Route 9 through a gap in Short Hill — with a few dozen buildings, its own mayor and council, and a town tax on top of county taxes.
What is the Old Stone School?
The town's restored 19th-century school building at the center of the village, now used as a community and events space. It is the focal point of the town and the venue for most of what happens here.
What is it like living on Route 9?
Route 9 is a through route between Loudoun County and West Virginia, and the town's one street is that road. Traffic and heavy vehicles pass close to the houses. The town has pursued streetscape and traffic-calming work to address it, but anyone considering a house here should stand outside it at rush hour before making an offer.
What schools serve Hillsboro?
Loudoun County Public Schools, generally the Woodgrove High School pyramid. Confirm the current attendance area for a specific address with LCPS.
Can you commute from here?
With difficulty by car — Route 7 via Purcellville is about ten minutes away and Leesburg twenty-five. The more workable option for a Washington commute is MARC or Amtrak from Harpers Ferry, a short drive northwest across the state line. Check current schedules and parking before relying on it.
Current Hillsboro listings are available through my search site.
Last updated 2026-09-08.