Debra Ann Woodside

life story

In Loving Memory

In Loving Memory of Debra Woodside (1968 – 2025)

Debra Woodside, a devoted mother, loving partner, and dedicated professional, passed away peacefully on May 3, 2025, just one day shy of her 57th birthday.

Born on May 4, 1968, Debra brought warmth, resilience, and unwavering care to every corner of her life. Over the span of more than 15 years, she built a respected career in property management, earning the trust and admiration of colleagues and clients alike through her integrity, work ethic, and deep understanding of people.

At the heart of Debra’s world were her three beloved children: Analise Bruno, Ariana Bruno, and Kevin Woodside. She was endlessly proud of them and found her greatest joy in their accomplishments and presence. Debra also shared a life of companionship with her partner, Bernardo Bruno.

Debra was the cherished daughter of the late Frances Hibbard (Sandulli) and Richard Hibbard, and the sister of Robin Lennon. She carried her family’s strength, kindness, and love through every chapter of her life.

Debra’s presence lit up every room. She had an innate ability to make others feel seen, heard, and cared for. Her memory will live on in the lives she touched—with every kind gesture, every piece of advice, and every moment spent in her loving embrace.

She leaves behind a legacy of strength, compassion, and deep familial love.

A funeral service to celebrate Debra’s life will be held on Friday, May 16, 2025, at 10:00 a.m. at Sacred Heart Parish, located at 45 Brooks Street, East Boston, MA 02128.

Flowers may be sent directly to the church prior to the service.

Rest peacefully, Debra. You will be forever missed.

About Debra

Debra Woodside was a fearless, loving woman whose strength, warmth, and incredible sense of style left a lasting impression on everyone who knew her. Born on May 4, 1968, Debra lived a life full of compassion, grace, and unshakable devotion to her family. Her children—Analise Bruno, Ariana Bruno, and Kevin Woodside—were her entire world, and there was truly nothing she loved more than being their mom (except maybe a pack of Twizzlers).

For over 15 years, Debra worked in property management, where her professionalism, integrity, and kindness earned her the admiration of colleagues and clients alike. Outside of work, she had a vibrant personality, a love for fashion, and a gift for making others feel cared for and seen.

Debra bravely fought cancer for a year and a half with the same strength and courage she showed in every part of her life. She passed on May 3, 2025, surrounded by love.

She is survived by her three children, her partner Bernardo Bruno, and a community of family and friends who will carry her memory forward with love, laughter, and gratitude.

Favorite Memories of Debra

Debra Woodside filled our lives with warmth, laughter, and countless beautiful moments that will never be forgotten. She had a way of turning ordinary days into something special—whether it was a quick trip to Trader Joe’s or a cozy movie night snuggled up with her daughters. She found joy in the little things, and made sure the people she loved felt it every single day.

One of Debra’s greatest joys was being in the kitchen. She was a wonderful cook, and nothing brought the family together like her famous Sunday gravy. Those Sunday meals were about more than just food—they were about love, tradition, and the comfort of home. Her cooking was an extension of her heart, and her kitchen was a place where everyone felt welcome and cared for.

She also loved sharing experiences with her kids, especially traveling to Disney World years ago—a trip filled with laughter, magic, and memories that still make us smile. Going out to dinner at the Ninety Nine with her daughters was another favorite tradition. It didn’t matter what was on the menu—what mattered was being together.

Debra created a home full of love and made every moment count. Whether through a lovingly prepared meal, a spontaneous outing, or simply being present, she gave her family a lifetime of memories they will hold close forever.

memorial service

Funeral

May 16, 2025

Sacred Heart Parish 45 Brooks St, Boston, MA 02128, USA

Flowers may be sent directly to the church prior to the service.

Funeral/Cremation Provider: Casper Funeral & Cremation Services