Judy Ann Principi

Judy Principi, age 78 of Englewood, Florida, formerly of Oxford, CT passed away on May 21, 2026. She was the daughter of the late Robert and Dorothy Hamilton and grew up in Greenwich, CT. She leaves behind a legacy of fierce love, quiet strength and unwavering devotion to people she held closest.

Early on she worked as a secretary but quickly realized that her calling was in the field of hospitality where her friendly personality and smile served her well. She worked at Jimmies Place in Seymour, CT for most of her career where she made lifelong friends and married the love of her life, Jimmy. She belonged to many clubs and organizations and was instrumental in organizing and sponsoring the annual Memorial Day Parade always followed by an open door policy of free food for any veterans that marched. In 2014 she retired to Florida with her husband where they lived their best lives golfing, beachcombing for shark teeth, and spending hours fishing on their boat in the Gulf of Mexico. She found incredible joy in the simple things; a crowded table in her home at holiday time, reading, walks on the beach, going to the casino and playing Scrabble with her best friend Joyce, gardening, baking her famous banana bread to share with friends and neighbors, playing cards and cribbage and making thousands of rosary beads over the years as service to her church. Despite her fear of flying, she was able to enjoy travel as often as she could, including an Alaskan cruise and a bucket list cruise to Ireland and Scotland in 2023 with her daughter…where she tried her first beer ever. A Guiness no less!

Judy was the first to help, no questions asked, if someone needed a meal, a ride or a strong shoulder and was the first to arrive with food and gifts in times of both celebration and loss.

She never missed an opportunity to welcome you into her home and fill you with great food and drink; even if you weren’t hungry or thirsty!

Those left to cherish her memory include her daughter Lisa Fair, son-in-law Joseph Fair, stepdaughter Judy Principi, stepson James Principi and wife Judy, daughter in law Deirdre Caruso, sister Lynne Hamilton, brother Peter Hamilton and wife Linda, grandchildren James, Christopher, Nicholas, Zachary, Nick and Michael, her feline snuggle buddy Chi Chi, numerous nieces and nephews and a countless list of loving friends. She is predeceased by her husband James Principi, beloved son Tommy Caruso, and brothers John Hamilton and David Hamilton.

We let go of a remarkable woman, a loving mother, a doting grandmother and kind soul. As we mourn her loss, we also celebrate the love, joy and kindness that were the essence of Judy’s being.

A celebration of life will be held later this summer. In lieu of flowers please consider a donation to the Unity Farm Sanctuary by mailing a check to 17 Unity Lane, Sherborn, MA 01770 or by visiting https://www.unityfarmsanctuary.org/ or St. Jude’s Children’s Hospital by mailing a check to 501 St. Jude Place, Memphis, TN 38105 or by visiting https://www.stjude.org/