Carole A. Bailey (née Sears), beloved wife, mother, grandmother, sister, and friend, passed away peacefully at home on April 7, 2025, in Plymouth, Massachusetts, surrounded by her loving family. She was 86 years young.
Born in Medford on Feb. 20, 1939, to Chester and Helen Sears, Carole spent her early years in both Medford and Point Shirley, Winthrop. A graduate of Medford High School’s Class of 1957, she began her professional journey as a model after completing her studies at the Academie Moderne in Boston and working with the Hart Modeling Agency. Over the years, she held a variety of other roles reflecting her versatility, including secretary for the Sports Publicity Department at Boston College and traffic supervisor for the Wilmington Police Department. Of all her life’s work, however, her most cherished role was as a devoted wife, mother, and grandmother.
Carole is survived by her husband of 65 years, Warren Bailey, and their four children: Helen (Gordie) Fitch of St. Pete Beach, FL; Stephen (Jeanne) Bailey of Towson, MD; Kathleen Bailey of South Yarmouth; and Todd (Colleen) Bailey of Ashland. She was the proud grandmother of nine grandchildren: Megan, Gordon, Madison, Hannah, Ryan, Seth, Lauren, Natalie, and Grant.
She is also survived by her loving sister, Helen Sears, and was predeceased by her two older brothers, William “Billy” Sears and Chester “Chick” Sears.
In 1961, Carole and her husband, Warren, moved to Wilmington, where they raised their family and made their home for 34 years. After retirement, they settled in Plymouth, where they enjoyed the company of family and friends.
Carole came from a talented family of entertainers and carried that spirit with her throughout her life, performing in community theater and various charity events. She had a beautiful singing voice and taught herself to play both the piano and the guitar, often filling her home with music. She loved to entertain, and her parties were legendary – filled with laughter, good food, great company, and her quick-witted humor. Whether it was a costume party, a dinner gathering, or a holiday celebration, Carole made sure everyone felt welcomed and had fun. She found happiness in life’s many pleasures – cooking, bowling, golfing, swimming, skiing, traveling, playing games with family, and cheering on Boston sports teams.
A devoted Catholic, Carole served as a lector and eucharistic minister at both St. Thomas of Villanova Church in Wilmington and St. Peter’s Church in Plymouth. Her faith, warmth, humor, and love for her family were the foundation of her life and the legacy she leaves behind.
A wake will be held at Cartmell-Davis Funeral Home, Route 3A in Manomet, MA, on April 30, from 4 to 7 p.m. A funeral Mass will take place the following morning, May 1, at 10 a.m. at St. Peter’s Church in Plymouth, followed by a luncheon at Mezza Luna Restaurant in Buzzards Bay. An interment ceremony will take place at 2:30 p.m. at the Massachusetts National Cemetery in Buzzards Bay.
In lieu of flowers, the family requests that donations be made in her name to St. Jude Children’s Research Hospital.
For more info and to sign the online guestbook please visit the funeral home’s site.