Fishing 16

David D. Caldwell, Sr.

October 15, 1958 ~ July 7, 2023 (age 64) 64 Years Old


David D. Caldwell, Sr., 64, of Winchester, passed away on Friday, July 7, 2023, at Reid Health in Richmond.  He was born on October 15, 1958, in Winchester to Darrell Caldwell and Bessie Jean (Williams) Wynn.

David was a truck driver.  He enjoyed rock and roll and fishing, and loved college sports, especially the Colts.  He also enjoyed eating biscuits and gravy.

David is survived by his children, David (Tammy) Caldwell, Jr. and Cheyenne Caldwell; the mother of his children, Diane Caldwell; brother, Chris Caldwell; sister, Angie Timmons; step brother, William “Billy” Cox; step children, Chris Young and Jessica (Phillip) Hawley; grandchildren, Aiden and Maeson; step grandchildren, Jillian, Pippa, Terrance, and Aaliyah; and two nieces and one nephew.

David was preceded in death by his parents; and a step brother, Greg Cox.

A memorial service will be announced at a later date.

Walker Funeral Home in Winchester is entrusted with the arrangements. Online condolences may be shared with the family at

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Services are to be announced


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