Sheila Diane Bailey

**Obituary for Sheila Diane Bailey (née Oliver)** *April 15, 1955 - September 30, 2025* It is with profound sadness that we announce the passing of Sheila Diane Bailey, beloved mother, grandmother, sister, and friend, who departed this life on September 30, 2025, in Auburndale, Florida. Born on April 15, 1955, in Winter Haven, Florida, Sheila was the cherished daughter of Thomas and Jeannette Oliver. She grew up alongside her siblings, Pam, Terry, and Melissa, nurturing bonds that would last a lifetime. A proud graduate of Auburndale High School, class of 1973, Sheila dedicated over 40 years of her life working at State Farm, where her professionalism and kindness touched the lives of many. She was known for her generous spirit and unwavering loyalty, leaving a lasting impression on her colleagues and clients alike. Sheila's legacy extends beautifully into the lives of her children: Heather Shapiro, Tony Cooley, and Brian Cooley. She was a doting grandmother to Kien and Kaia Shapiro, as well as Abigail, Ivy, and Samuel Cooley, who provided her with endless joy and love. Sheila’s understanding and loving nature made her the heart of her family, always encouraging and supporting those around her. Sheila had many passions—she loved sewing and crafting, creating beautiful pieces that reflected her generous spirit. Her enthusiasm for playing cards brought smiles and laughter to her family gatherings. She cherished traveling and enjoyed fishing fry's and oyster stew, often sharing these delights with her loved ones. A celebration of Sheila's life will be held on [Date to be inserted], at First Missionary Baptist Church, 406 Main Street, Auburndale, FL 33823. Visitation will begin at 10 AM, followed by a service at 11 AM, and a gravesite visit to lay Sheila to rest. A lunch will be provided at the church post-service for all who wish to gather and share memories of her life. In honor of Sheila’s loving memory, the family requests that flowers be sent directly to the church. She leaves behind a legacy of kindness, generosity, and humor that will be missed deeply by all who knew her. As we remember Sheila Diane Bailey, let us carry forward the love and joy she shared with us throughout her life.