Jason Vickers is President of the Board of the Middleburg Community Center and President of DocWeek Middleburg. He is also the Chief Operating Officer of OakCrest Companies in Winchester, Virginia, where he oversees operations for ERA OakCrest Realty, OakCrest Commercial Realty, OakCrest Properties, and OakCrest Builders, Inc.
 
OakCrest is a family-owned and operated real estate, construction, land development, and property management firm that has served the Winchester community for more than 50 years.
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A Winchester native, Jason was a collegiate tennis player and remains active in the sport, regularly playing at the Middleburg Tennis Club. He moved to Middleburg in 2018 after spending 12 years in Manhattan, where he owned and operated a talent management firm representing clients in the film, television, and fashion industries.
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Jason is passionate about strengthening community institutions and supporting initiatives that enhance the cultural and civic life of Middleburg.