Charles R. Ashley Sr., 88, of Millsboro, Del., formerly of Baltimore, Md., passed away on Sunday, Oct. 3, 2021, at Beebe Healthcare in Lewes, Del. He was born in Rush, Ky., son of the late Willie Ashley and the late Mollie (Osborne) Ashley.

Ashley proudly served his country in the U.S. Army during the Korean War. He was a hardworking man and was talented in many facets of his life. He owned several businesses over the years, including two taverns in the Baltimore area. He was also involved in real estate, with buying and personally remodeling homes in the Baltimore area and in southern Delaware. He designed and engineered many farmhouses, homesteads and waterfront property.

He enjoyed woodworking, was a great historian and had an incredible memory. He opened his home to family and was a gracious host to many. He easily made friends and was willing to help his neighbors with any project.

In addition to his parents, Ashley was preceded in death by his first wife, Laureen Ashley. He is survived by his loving wife of 22 years, Theresa (Kennedy) Ashley; a son, Charles R. Ashley Jr.; a stepson, Dave Ward and his wife, Tele; a loving grandchild, Tris Ward; and many other loving family members and friends.

He left his footprint in the hearts of everyone that met him.

Service and burial were to be private. In lieu of flowers, the family suggested memorial contributions in Ashley’s name to the Beebe Medical Foundation, 902 Savannah Rd., Lewes, DE 19958. Condolences may be sent online by visiting