Anne Tredennick Cleary, “Annie,” 79, of Osterville, Massachusetts, died peacefully on September 6, 2026, at Massachusetts General Hospital in Boston, with her children by her side.
One of six children, Annie was born in Hartford, Connecticut, on March 23, 1947, and grew up in Meriden, in the beloved family home known to all as the Big House. She moved to Boston to attend the Katharine Gibbs School, and fell in love with life in the city — living there and working in the world of advertising at Hill Holliday. Her working years were brief but formative: it was in that chapter of her life that she met Robert B. Cleary. They were married at the Big House in 1976, and Annie turned to what she considered her true calling — raising her family. She and Bob shared thirty-nine years together until his death in 2015.
Weston was home for much of her life, complemented by treasured seasons in Osterville on Cape Cod and in Jupiter, Florida. In her later years, Osterville became her home. Oyster Harbors Club, Brae Burn Country Club, and The Loxahatchee Club were each a cherished part of her life.
Above all, Annie was devoted to her family and friends. Raising her children and delighting in her grandchildren was the joy of her life. She shared an especially close bond with her three sisters, and gave that same steadfast love to a circle of fiercely loyal friendships she kept for decades. That devotion took shape in what she made by hand: her needlepoint and decoupage were never merely pastimes but expressions of her love for others. Her decoupage pieces, each carrying her personal touch and a flourish of her signature pink, made their way to family and friends. Most treasured of all were the Christmas stockings she stitched by hand, keepsakes that hold a lasting place in the lives of many. Every Christmas she made English toffee and gave it out to all, a treat so beloved that everyone looked forward to it. She also loved building gingerbread houses with her grandchildren. Loving, caring, loyal, and honest to a fault, she was happiest in good company — on the tennis court, on the golf course with her women friends, or beside her many Westies, long a family trademark. More recently, she had taken up mah-jongg with real devotion, treasuring the hours spent learning and playing the game alongside her friends.
She was predeceased by her husband, Bob, and three of her siblings: her brother Mark Tredennick and her sisters Nicky Doyle and Mary Gould. She is survived by her children, Meghan and her husband Peter, and Andrew and his wife Emily; her stepchildren, Robert, Christin and her husband Rick, Brian; ten grandchildren — Henry, Gus, and Georgia; Drew, Claiborne, and Evelyn; Alexandra, Robert, and Christopher; and Chloe; two great-grandchildren, Emmett and Carter; and her siblings Stephen Tredennick and Alexandra “Coe” Barakos.
Visiting hours will be held at the George F. Doherty & Sons Funeral Home, 477 Washington St, (Rt.16), Wellesley on Thursday, September 10, from 4:00 to 7:00 p.m. A funeral Mass will be celebrated at St. Julia Parish in Weston on Friday, September 11, at 10:30 a.m., followed by burial at Linwood Cemetery in Weston. A reception will follow at Brae Burn Country Club in Newton.
In lieu of flowers, gifts in her honor may be sent to the MGB Cancer Institute Development Office, 399 Revolution Drive, Somerville, MA 02145, or visit give.massgeneralbrigham.org or The Boys & Girls Clubs of Boston, 200 High Street, Suite 3B, Boston, MA 02110, Attn: Beckie Crawford.