About Will Driskill | Middleburg, VA Real Estate Agent

Meet Will

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.

PHONE

(540) 454-7522

[email protected]

LICENSE NUMBER

0225248385

ADDRESS

2 S Madison St Middleburg, VA 20117

Testimonials

I have worked with many realtors, and there is nobody better than Will for buying and selling in VA horse country. He has extremely deep roots in the area, knows just about everyone, and is intimately familiar with the properties and their values. He is patient, friendly, and professional working both sides of the real estate transaction. I highly recommend working with him when buying or selling a property. - Dave and family

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Testimonials

Dave and Family

I have worked with many realtors, and there is nobody better than Will for buying and selling in VA horse country. He has extremely deep roots in the area, knows just about everyone, and is intimately familiar with the properti...

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Karen & Ian Landy

Will worked tirelessly for us in search of a Virginia farm not too far out, but most importantly with ‘long views’. After countless visits to spectacular properties throughout the area he encouraged us to look at a Clarke Count...

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Jennifer Long

I am delighted to recommend Will Driskill as a realtor in Middleburg, Virginia. Will recently helped me sell my antique house, and his expertise made all the difference. He is incredibly knowledgeable about the local market, an...

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Five formally dressed riders on horseback travel along a wet, tree-lined country lane.

William Driskill is a licensed Virginia real estate professional with Thomas & Talbot Estate Properties.

With deep roots in Virginia’s Hunt Country, his unparalleled market knowledge and relationships drive consistent results, with more than $140 million in career sales and recognition as a Top Producing Agent at the firm. Will represents clients from Western Loudoun, Fauquier, Clarke, Rappahannock, Warren, Culpeper, and Orange counties, facilitating transactions that include historic estates, residential retreats, equestrian properties, and significant land acquisitions.

Raised in the Piedmont Countryside

Will attended The Hill School and Highland School before continuing to Hampden-Sydney College, where he played Division III tennis. He remains closely connected to his community, serving on The Hill School Alumni Board and Middleburg Humane Foundation Board, and as a member of the Middleburg Tennis Club.

An avid horseman, Will participates in both the Orange County and Piedmont hunts. His commitment to conservation and land stewardship has led to his involvement with the Piedmont Environmental Council (Junior Member), the Goose Creek Association, the Blue Ridge Wildlife Center, and the Virginia Thoroughbred Association.

Professional Affiliations

Will’s professional affiliations include the Greater Piedmont Realtors Association (GPAAR), the National Association of Realtors (NAR), and the Bright MLS. He demonstrates a well-rounded background, representing residential, farm, and commercial transactions in addition to estate and equestrian properties. His 2025 record, with $56 million in sales, reflects Will’s expert insight and inherent understanding of countryside living in Virginia.

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.

Neighborhood Guides

Each area offers its own relationship with the land, local traditions, and the broader Hunt Country lifestyle.

Aerial view of a golf course, homes, and pond beneath a golden sunset.

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He is dedicated to helping you find your ideal Hunt Country property and guiding you through every step of the selling process. Connect with Will today to get started!

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