A third-generation Middleburg resident, Will Driskill’s lifelong connection to Virginia’s Hunt Country has shaped his career in real estate. Rooted in the region’s equestrian traditions, land stewardship, and the character of the Piedmont countryside, he brings unparalleled local insight to every transaction. His expertise spans historic estates, residential retreats, equestrian farms, commercial properties, and land acquisitions across Loudoun, Fauquier, Clarke, and the surrounding counties.

Since 2021, Will has closed more than $140 million in sales, including $56 million in 2025 alone. For buyers and sellers seeking an advocate who knows both the landscape and the lifestyle of Hunt Country, Will offers informed guidance, exceptional service, and long-standing dedication to the place he calls home.