Sandra Chesteen Sproles

Sandra Chesteen Sproles, died Wednesday, January 15, 2025 at Tyler Holmes Memorial Hospital in Winona, MS, surrounded by her husband and children. Sandra was born on August 3, 1936 in Winona, MS. She was the daughter of Joseph Pullen Chesteen, Geneva Walker Bailey and Pete Bailey. Sandra was a devoted follower of Christ, a successful business owner, a loving family woman, active member of her church and community, and “gran” to many beyond her family.

Sandra married her first love, Charles Robert Sproles Sr. in 1954. Sandra and Charles were married for 70 years. They were lifelong companions and Sandra devoted her life to care for her household. They were blessed with four children: Sandra Lynn, Chuck, Gib, and Stephanie; eight grand-children, and twenty-three great-grands.

Sandra was first employed at McGregor shirt factory. She then moved on to working for many years at the Bank of Winona before becoming a successful business woman. She devoted most of her adult-life to owning and operating Winona Printing and Office Supply, along with Sports, Tees, and Jeans, Stephanies, The Male Side and The Picket Fence. After turning over her business to her children, she became a vital part of co-managing Norris Bookbinding with her husband, Charles. Once she retired, she spent many afternoons assisting Charles with other business adventures.

She was a devoted member to her church family and her community. She was a member of First Baptist Church from her childhood throughout her adult years. There she was involved and made a life-long community of friends. She was an avid member of the Montgomery County Economic Council, where she made a host of acquaintances, wherein she was honored as “Retail Person of the Year”.

During her free time, she was a caring grandmother. She had the luxury of having all of her children and grandchildren close by. She would spend many afternoons and nights on the road taking kids from place to place, at sporting events, dance recitals, and much much more. She was a lover of her home and enjoyed spending time there with her loved ones. From swimming, watering plants, telling the kids to slow down on four wheelers, providing snack upon snacks, hosting endless events, and so much more. She was proud to wear the title “Gran” and wore it effortlessly.

Sandra is survived by her husband, Charles; three kids, Sandra Lynn Sproles, Gib (Theresa) Sproles and Stephanie (Joby) Jackson; eight grandchildren Robin Rose (Will), Brad Sproles, Jennifer Ingram (Ben), James Barry Carpenter Jr., Walker Jackson (Rachael), Wilson Sproles (Caitlyn), Miles Jackson (Shelby), Eliot Jackson; twenty three great-grandchildren; along with many nieces and nephews.

She is preceded in death by her parents, Joseph, Geneva, and Pete; her son, Charles Robert “Chuck” Sproles Jr. (Debra); her two sisters Robbie Cooper and Guyula Harris and two brothers, Lucian Chesteen and Richard Chesteen; her great-grandson, Emerson Sproles.

Sandra will be remembered for many things, especially the love for her Savior and family, her infectious laugh, her spunk, her love for people and her warm spirit.

Funeral arrangements will be held Sunday, January 19, 2025 at First Baptist Church – Winona, MS. Visitation held at 2p.m. funeral following at 3p.m with burial following in Winona Garden of Memory. Rev. Jay Anderson and Dr. Kevin Jackson will officiate the service. Pallbearers will be Brad Sproles, James Barry Carpenter, Jr., Walker Jackson, Wilson Sproles, Miles Jackson, and Holland Ingram.

In lieu of flowers, donations can be made in honor of Sandra Lynn Sproles resident of North Mississippi Regional Center.