David Michael Winchester, Sr., 73, of Newberry, died Monday, May 16, 2022 at Prisma Health Baptist Hospital. Born on December 14, 1948 in Union, he was a son of the late H. B. and Margaret Hooper Winchester. David began his career as a handyman doing construction repairs for various companies. Over time, he amassed several homes and began his own rental property business. As a businessman, David became involved in his community, joining the Newberry Moose Lodge, attending various county and city meetings, and growing his property portfolio. David was a collector – antique cars, collectibles, guns, books, shells. He enjoyed visits to the beach, especially rising early to collect shells. He was an artist, often painting pictures on glass bottles he had collected. David loved his friends and family. He cared for his tenants, always asking how they were doing, extending a little extra help when needed, and "talking junk and picking with them" whenever he could. They were a part of his extended family. He enjoyed spending time with his family, sharing his hobbies, his passions, and often his workload. He loved family dinners, and he was especially good at planning them so that his son David, Jr. would do the cooking. David may have been "a little rough around the edges" at times but those who knew him knew, he was loving and caring on the inside. He is survived by a son, David M. Winchester, Jr. (Sheri) of Newberry; daughter, Shanon Winchester (Melanie) of Newberry and Sarasota; brother, Barry Winchester; niece and nephews, Wendy, Barry Jr. and Todd; grandchild, Ashley Morgan; step-grandchildren, Dustin Moon, Nathan Reda, and Alexander Reda; step-great grandchildren, Cadie and Jacob Moon; great-niece and nephews, Alayna, Brayden and Holdyn New; and special friends, Mary and Leroy New. David was predeceased by his wife, Debbie Graham Winchester; daughter, Kristy Winchester; and siblings, Doug Winchester, Mack Winchester, and Brenda Winchester. The family will receive friends at Whitaker Funeral Home on Sunday, May 22, 2022 from 3:00 PM until 5:00 PM. Funeral services will be held at Whitaker Funeral Home, Newberry on Monday, May 23, 2022 at 10:00AM. For those wishing to join services online, live streaming options are available either by clicking the link here: "Click Here for Livestream Services for David M. Winchester, Sr." or by clicking the Watch Event Link on the Events section. Burial will follow at 1:00PM in Union Memorial Gardens, 1720 Whitmire Hwy, Union, SC 29379. Pallbearers will be Barry Winchester, Jr., Leroy New, Sammy Taylor, Mike Felker, Tatiana Swittenburg, and Martin Avila. Memorials are suggested to Newberry County Humane Society, PO Box 485, Newberry, SC 29108. Memories and messages may be shared with David's family on his tribute page at www.whitakerfuneralhome.com Whitaker Funeral Home is honored to assist the family.