Meet Your Neighbor: Drew MacMahon at Windy Hill
Written by Diane Helentjaris | Photo courtesy of Drew MacMahon
Teacher and child psychologist Haim Ginott believed, “Children are like wet cement. Whatever falls on them makes an impression.” What impressed little Drew MacMahon as he grew up in Middleburg was a person — his father, Paul. He listened from an early age as his dad spoke to his customers, hearing words like “property,” “square footage,” and “three-bedroom.” But now, as an adult, what really amazes him is that his father somehow managed to ferry his three sports-loving sons to “every game” they played. He “is a great role model,” Drew says. Paul’s dedication to his family and customers — along with his time management skills — left an indelible mark on his son.
Drew fondly recalls living amid the swirl of the busy family real estate company his grandmother had established. Now, all three MacMahon sons have continued in the family trade. After graduating from James Madison University with a bachelor’s degree in sociology and business, Drew initially worked in property management and sales. In Washington, D.C., and Raleigh, North Carolina, he dealt with many high-end, luxury properties.
Two years ago, in a bit of a career change, he left the private sector, returned to Middleburg, and became the president of operations for the Windy Hill Foundation. Though he also continues to do real estate work for the family business, Sheridan MacMahon LTD Realtors, his primary focus is Windy Hill.
The Windy Hill Foundation began in the living room of Irene Llewellyn, an English woman who came to Hunt Country as a war bride in 1945. She became aware of the poor living conditions on Windy Hill Road when she gave one of her music students a ride home. There, on the west side of Middleburg, 15 African American families lived in “cottages” that had originally been horse stables and stalls. They were unheated and had dirt floors. Two spigots provided the only drinking water. Toilet facilities were limited to six outhouses.
Llewellyn, who had been presented as a debutante at British court to King George V and Queen Mary, believed in the power of philanthropy. As a young wife and mother in England, she had been active in charity work and continued that after her move to Virginia. In 1970, she established Middleburg FISH, an organization providing temporary financial assistance to those in need. Alerted to the situation at Windy Hill, she enlisted her friends and the Windy Hill families. One friend she took to see the neighborhood immediately wrote a $10,000 check. Her bridge club made an initial donation of $100,000. By 1981, the 501(c)(3) nonprofit foundation was organized. Today the Windy Hill Foundation provides housing to over 850 Loudoun and Fauquier County residents. It also provides scholarships and other supportive services.
As president of operations, Drew has overseen recent renovations of the original Windy Hill Road cottages. He taps into skills he developed in the private sector, concentrating on consistent and excellent service. He “tries to uphold himself to the Windy Hill Foundation standard, to make sure people have a safe place to go home to at night.” He finds it “rewarding to apply in my hometown [what he’s learned] and help a lot of people… When people think of Middleburg, they don’t think of affordable housing, but [Windy Hill] owns 18% of the housing in Middleburg.”
In addition to the world of real estate, sports continue to be a part of Drew’s life. He is a professional soccer referee for international and US soccer games, and works with the NCAA as well as local high schools. It “keeps me fit,” he says, while acknowledging that both real estate and soccer are “high-emotion, high-intensity” activities.
Home can mean many things. Drew MacMahon, with the inherent fairness of a professional referee, believes it should mean housing that is safe, affordable, and decent. He also believes his father is “proud of me. I can honor him in my own way… I can honor his legacy.” ML
More information about Windy Hill Foundation is available at windyhillfoundation.org.
Published in the September 2026 issue of Middleburg Life.