Hillsboro is Loudoun’s smallest town, with its most contemporary structure dating to the late 1800s and was described by an early traveler as "a town made of stone."
The town was previously known as The Gap due to its favorable location on the Vestal's Gap Road, but striving for a more alluring name than The Gap, Mahlon Roach, the first postmaster, chose Hillsboro (spelled Hillsborough until its 1880 incorporation), meaning "a shelter in the hill."
Named appropriately for its geography, the wineries around Hillsboro offer some of the best views in the county. From the terrace outside Hillsborough Vineyards, visitors experience luxuriant gardens and trickling fountains, dramatically framed by the Blue Ridge Mountains.
Hillsboro Homes For Sale
- 17213 Magic Mountain Dr, Round Hill, VA 20141
- 5 Beds · 4 Baths · 4366 Sqft
- Welcome to Magic Mountain Drive in the idyllic town of Round Hill, Virginia. Conveniently located near Route 7 in wester ..
- 39524 Rodeffer Rd, Lovettsville, VA 20180
- 4 Beds · 3 Baths · 4524 Sqft
- Peace and privacy is waiting for you. Situated on nearly 7 acres and conveniently located just outside of the quaint tow ..
- 24419 Haven Ridge Ln, Aldie, VA 20105
- 5 Beds · 5 Baths · 5312 Sqft
- The Grove at Willowsford is an award winning community offering every amenity for a life well lived. With over 5, 300 fi ..
- 16546 Loneoak Pl, Hamilton, VA 20158
- 4 Beds · 5 Baths · 4200 Sqft
- Welcome to Lone Oak where you have the best of all worlds! A beautiful turn key and well cared for home in an establishe ..
- 16571 Loneoak Pl, Hamilton, VA 20158
- 5 Beds · 5 Baths · 5959 Sqft
- Resting beautifully on 4 rolling acres, this 6, 000 finished square foot home is just outside the quaint town of Hamilto ..
- 11439 Olde Stone Ln, Lovettsville, VA 20180
- New price, Just reduced by $44K! Ready to build your dream home in complete peace and tranquility? Seller has made subst ..
- 816 Kinvarra Pl, Purcellville, VA 20132
- 4 Beds · 4 Baths · 3148 Sqft
- Enjoy in town living in quaint and sought after Purcellville. Walk and ride to shopping, recreation, schools, you name i ..
- 16522 Loneoak Pl, Hamilton, VA 20158
- 5 Beds · 5 Baths · 4936 Sqft
- Tranquil in the outskirts of the town of Hamilton, a place to spread out and get away from it all while still being conv ..
- 717 Sunflower Ct, Purcellville, VA 20132
- 4 Beds · 3 Baths · 3436 Sqft
- This home shows like a model! Welcome home to Sunflower Court in Western Loudoun's Locust Grove neighborhood. This 4 bed ..
- Samson Properties 1602 Village Market Blvd SE, Suite 255, Leesburg, VA 20175
- Mobile (703) 615-1493
- Broker Office (703) 378-8810
- Email firstname.lastname@example.org
- Areas Served Purcellville, Leesburg, Ashburn, Hamilton, Round Hill, Waterford, Round Hill, Middleburg and the entire No VA region