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Carol Lee (Shepard)
Santilli
Aug 19, 1940 — Jun 21, 2026
Toomey-O’Brien Funeral Home
11:30 am - 1:00 pm (Eastern time)
Toomey-O’Brien Funeral Home
Starts at 1:00 pm (Eastern time)
Massachusetts Memorial Veterans Cemetery
Starts at 2:00 pm (Eastern time)
Carol Lee (Shepard) Santilli, 85, passed away peacefully on Sunday, June 21, after a long and courageous battle with emphysema, which was further complicated by other health issues.
Born in Springfield on August 19, 1940, she was one of three children born to the late Harold and Mary (Hannigan) Shepard. A lifelong resident, Carol graduated from West Springfield High School in 1958, where she played trumpet in the band and was a cheerleader. After graduating, she met the love of her life at Hampton Ponds, and they soon married and began their family.
Carol was a devoted mother and homemaker. A talented seamstress, she made clothes for her children, window curtains, and especially enjoyed creating Halloween costumes. Carol also played a significant role in nurturing her son Mark’s love of music, arranging drum lessons for him at a very young age—and patiently standing by as he practiced each week. She also influenced her daughter’s love of fashion, often designing outfits. Carol had a flair for artistic expression and a unique personal style. When she walked into a room, she stood out.
As her children grew, Carol ventured into the workforce. She worked for the former Speed & Hegeman as a licensed insurance agent for more than 40 years, and continuing on when the business was acquired by McClure Insurance Agency. Carol remained with McClure until retiring at age 75, ready to begin her next chapter.
After the loss of her daughter, Doreen, in 1998, Carol returned to sewing as a way to cope. She later co-founded and operated Kountry Kousins with her sister-in-law, Janet, marketing handcrafted items such as pocketbooks, scarves, banners, stuffed animals, and holiday decorations. There was little she couldn’t create.
Following the passing of her husband, Al, in 2010, Carol developed a passion for gardening. She took pride in planting beautiful flowers, designing her own landscaping, and even mowing the lawn. Fiercely independent, she was proud to do things her way and often said she wouldn’t have it any other way.
Back in the day, Carol enjoyed dancing at The Ivanhoe with her husband and friends, and traveling to destinations including Jamaica, Hawaii, Bermuda, as well as taking several cruises over the years.
She shared a special bond with her brother and best friend, Rick. Together, they were often described as “two peas in a pod.”
Carol was recently predeceased by her two lifelong friends, Annie Clapp and Nancy Haramut who she dearly missed.
In addition to her parents, Carol was predeceased by her husband, Albert Santilli, daughter Doreen (Santilli) McCarthy and brother Billy Shepard. She will be sorely missed by her son Mark Santilli and his wife Valerie, brother Rick Shepard and his wife Janet; grandchildren Michaela and Caitlin McCarthy; son-in-law Michael McCarthy; several nieces and nephews; and her sister-in-law Michelle Shepard as well as Al’s family in Uniontown, PA.
Calling Hours will be 11:30am-1pm on Monday, June 29, with a Funeral Service at 1pm, all at TOOMEY-O’BRIEN FUNERAL HOME, followed by 2pm committal at the Massachusetts Memorial Veterans Cemetery in Agawam.
In lieu of flowers, consider a donation in Carol’s name to St. Jude’s Children’s Hospital, 262 Danny Thomas Place, Memphis, TN 38105 or to Shriners Hospital for Children, 516 Carew Street, Springfield, MA 01104.
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