Deanna Calandrillo of New Port Richey, Florida passed away on January 2, 2026 at the age of 86. Deana was born in Revere, Massachusetts on February 24, 1939 to Peter DiStasio and Ann Lizzo of Revere, Massachusetts.
Her father Peter DiSasio was a veteran of World War II, and was killed in action.
Her mother Ann was remarried to William Seydak of Watertown, Massachusetts, where Deanna lived with her parents as a child.
Deanna attended Rosary Academy High School in Watertown, Massachusetts.
Upon graduation she was accepted into The American Academy of Dramatic Arts in Manhattan, New York.
She is survived by her husband of 50 years, Dr. James Calandrillo of New Port Richey, Florida. He and Deanna spent a majority of their life in Hudson, Massachusetts, and later in Florida.
She is predeceased by her son Matthew Giglio Calandrillo, her mother Ann Seydak, her step-father, William Seydak, her Aunt Olympia Carbone, and numerous other uncles and aunts.
She is survived by sons: Adam Calandrillo and spouse Jacklyn Colgan of Land O’Lakes Florida, Jared Calandrillo and spouse Laura Wilson of Marlborough, Massachusetts, son, Mark Giglio and spouse Steven Sweet of Auburn, Massachusetts, son Chris Giglio and spouse Lisa of Hubbardston, Massachusetts.
She is also survived by her grandchildren, Marigold Calandrillo, Amanda Giglio, Matthew Giglio, Douglas Nading, Savannah Sweet Giglio, and Maynard Giglio.
Deanna led a true Piscean life, raising a large family, enjoying many beautiful and precious performance years on stage in community and professional musical theater jointly with her husband Jim.
Deanna played numerous leading theatrical roles in musical theater – twice playing Mama Rose in the musical, “Gypsy,” twice playing Blood Mary in “South Pacific,” playing Mother Abyss in “The Sound of Music,” twice playing Golda in “Fiddler on The Roof,” Miss Hannigan in “Annie,” and most recently Madame Thernadier, The inn Keeper’s wife opposite her husband as The Inn Keeper in “Les Miz.”
Deanna had a compelling coloratura soprano voice, and appeared in many community theater productions throughout Massachusetts, Marlborough and Hudson mostly.
She directed many high school short plays at Hudson High School in conjunction with friends Paul and Lynne Johnson’s competitive play series.
Deanna worked extensively with the metro-west and now Cape Cod director, friend Donna Wresinski in numerous theater productions.
Deanna also created a business called “Parrots Without Partners,” in order to rescue and raise exotic birds.
She worked as a vet tech for Dr. Sager of Acton, Massachusetts.
Deanna said that her proudest achievement were her sons and their families.
Brenda Calandrillo
January 10, 2026, 3:27 am
Jim, our sincere condolences to you and your family. May joyous memories always be your comfort.
Brenda & Frank Calandrillo
Sarah Baron
January 10, 2026, 4:03 am
Jim, So sorry for the loss of your wife. Please accept my deepest sympathies.
Diane Davis
January 10, 2026, 12:41 pm
My condolences go out to the family. Deanna was a wonderful caring person. She will be greatly missed.
Julia Slouber
January 10, 2026, 6:53 pm
To the family of Deanna, She was a joy to have known in my life.I have great memories of her I will treasure. All my condolences and sympathy to Jim and family
Debbie Dienstbier
January 10, 2026, 9:16 pm
What a beautiful soul! I will miss her beautiful singing voice! I hope to hear her singing with the Angels💝Her family is a wonderful reflection of her greatness as they stood by her and helped her to the doors of Heaven. This is the best gift you can give anyone! Soar with the Angels Deanna💕🙏💕
Chris Giglio
January 11, 2026, 3:31 pm
Mom was a loving mother to all of her children, she tried so very hard to raise them to love life and family. Mom’s first husband was was Joseph Giglio, she was married for 15 years, she had 4 children Mark, Chris, Matthew, and Adam Giglio. She spent the majority of her life married to Dad, in Bedford, MA. Mom has one sister Gail (Saydak) Hannon, Married to Robert Hannon of Bedford, Ma. Mom leaves behind nieces Robyn and Roxanne, and nephew Robert. Mom will be greatly missed by all. We love you Mom.
Robyn Hannon Brandy
January 12, 2026, 1:38 am
My heart ❤️ goes out to my family. Auntie was always loved and will always remain in my heart. She was beautifully unique and a special person. Fly high with the birds Auntie.
Patricia Seger
January 13, 2026, 1:05 am
My deepest condolences to Jim and family for the loss of Deanna. It was a great privilege knowing her and listening to her beautiful voice Rest in peace Sweet lady