Lola "Helen" Gregory

Devoted Wife, Mother, Grandmother, Great Grandmother and Great-Great Grandmother

Lola Helen Gregory (Helen) passed away peacefully and went to her eternal home on October 21, 2024 at 95 years old surrounded by her family and her family’s prayers. Helen was a gorgeous woman of immense love and wisdom who cherished every moment spent with loved ones. She lived a beautiful life, full of love, laughter, and strength. She was born on December 10, 1928 to Hershel and Mary Pearl Foxworthy in Indianapolis, Indiana. In 1947, she married her late husband, Willie C. Gregory and they began their family, which became her greatest joy. Her legacy includes her 10 children: John Gregory (Kathy), Bobbie Maynard (Ray), Carl Gregory (Robin), Marilyn Caldwell (Scott), Helen Faye Schob, Bert Dumas (Chuck), Doris Lewis, Jim Gregory (Debby), Bobby Gregory (Gina) and Mickey Gregory (Natalie). In 1971, Helen and Willie made Orlando their home. She worked in the restaurant industry for several years and then she obtained her Insurance Customer Service License and worked in two different Nationwide agency offices until she retired in her late 70’s. Her greatest joy was her family, including her 39 grandchildren, 39 great grandchildren and 3  great-great grandchildren and has another granddaughter on the way bringing the total to 100!

She will be remembered by her family and friends as someone who always put others first, welcomed anyone to delicious homemade Sunday dinners, fish fries, and holiday meals. She loved to spend time with her family during annual summer trips to New Smyrna Beach, read, and watch crime dramas. She signed every birthday card with “I love you very, very much.” She was patient and she was never happier than when holding a baby. Well into her late 80s, she ensured every new baby to the family received a homemade blanket and a Bible from Grandma/Great, Grandma/Great Great Grandma. 

She is predeceased by her husband, Willie C. Gregory, three daughters, Helen Faye Schob, Bert Dumas and Doris Lewis, as well as her parents and four sisters. She will be missed immeasurably by all who knew and loved her, but we know that she is watching over us from heaven, just as she did throughout her life. 

To celebrate Mom’s/Helen’s true spirit please feel free to wear bright color’s! A visitation will be held on Monday, October 28, 2024 from 5pm to 8pm at Carey Hand Colonial Funeral Home. A Funeral Service will be held the following day on Tuesday, October 29, 2024 at 10am at Carey Hand Colonial Funeral Home with  Internment to follow at Rose Hill Cemetery. 

“What we have once enjoyed and deeply loved we can never lose, for all that we love deeply becomes part of us.” – Helen Keller