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Deborah Caliolo

Obituary of Deborah Ellen Caliolo

Deborah E.(Cipriano) Caliolo, 64, of Watertown, formerly of the Town Plot section of Waterbury, passed away peacefully surrounded by her loving family on November 10, 2019 at the UCONN Health Center. Debbie was born March 2, 1955 in Waterbury, a daughter of the late Peter Cipriano and Helen (Gudas) Cipriano.

Debbie attended B.W. Tinker School in her elementary years and then graduated from Kennedy High School. After that, she worked in the Human Resource and Accounting Department for the hotel Industry and later retired from the State of Connecticut. She treasured her family and dogs. She enjoyed vacationing at the beach, taking long walks and collecting shells.  Her true passion in life were her children and grandchildren, whom she loved dearly. 

Debbie leaves to cherish her memory, her daughter Kristine and husband Toby DeLeo of Watertown, grandchildren Taylor, Samuel and and Ella Rose Kijak, with whom she made her home, her son William Caliolo of Waterbury, brother Dennis Cipriano, nephew Dennis Cipriano Jr., nieces Alicia Richelieu and Kristen Waybrightall of New Hampshire, and many more members of her extended family that remained very close to her throughout her life.

Most importantly, Debbie treasured her family and friends with all of her heart and soul, as they did her. She grew up “old school” in a loving home with nurturing parents and lost her mom at a very early age of seven. She had vigilant aunt and a big brother Dennis who absolutely adored her….that was just the first floor!  The next two floors up consisted of wonderful aunts, uncles and a band of cousins, who in essence, were a close knit Italian family. Her house as a whole had enough love and great food to sustain a small community.


Debbie grew up and married the late, Nicholas E. Caliolo, also from Town Plot and had two blessed children, Krissy and Billy. This is when her love blessed her family two-fold and her legacy began.  Her new in-laws adored Debbie and gave her unconditional love.  Her big brother-in laws and compassionate sister in-laws, gave her more love and friendships.  Deb also had relationships with her children’s friends that she treated with the same love and kindness as if they were her own.

Even with all of the affection that she shared and received from her elders, family and friends, Debbie’s true passion was the joy of her forever grateful children, grandchildren nieces and nephews. Debbie especially loved spending time with her grandchildren, Taylor, Sam and Ella. She attended all of their school talent shows, band and dance recitals, baseball games, swim meets, cheerleading competitions, loved watching movies and even brought them to orthodontic appointments, these kids filled her heart with joy. She continued to give her love back ten-fold to all that were special to her.

Debbie was the epitome of a mother, grandmother, sister, aunt, cousin, friend and woman.

Thank you Lord for blessing all of us with such a beautiful being, for she will truly be missed by all.

Until we meet again, rest in peace in heaven.

Friends and relatives may visit with Debbie’s family Friday, November 15, 2019 from 5 to 7 pm at Prospect Memorial Funeral Home, 72 Waterbury Rd., Prospect.  Burial will be at the convenience of the family.

In lieau of flowers memorial donations can be made to The American Heart Association at  or the Saint Vincent DePaul Mission of Waterbury Shelter, 114 Benedict St., Waterbury, CT 06705

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5:00 pm - 7:00 pm
Friday, November 15, 2019
Prospect Memorial Funeral Home
72 Waterbury Rd.
Prospect, Connecticut, United States
(203) 758-6008