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Contains letters, photographs, and other material related to the Winfree and McIlwaine families of Petersburg, Virginia. The bulk of the letters are addressed to Dr. John Winfree and are handwritten with envelopes. Most of the photographs are tintypes and pertain to the McIlwaine family, including photographs of William Baird McIlwaine, who attended the University of Virginia and became a doctor. Most of the letters have to do with business affairs, predominately of the Winfree family.