Kathleen Dee Winterling

Kathleen Dee Winterling, 76, of Easton, Maryland, formerly of Carmel, Indiana, passed peacefully at home surrounded by loved ones on Tuesday, October 7, 2025. Born September 17, 1949, at the United States Naval Academy Hospital in Annapolis, MD, Kathy was the cherished daughter of the late LCDR Raymond Jerome Clare Jr. and Jean Rodriguez Clare. She was preceded in death by her parents, her first husband, John Dee, her beloved son, Bryan Dee, and her dear sister, Irene Nolan. Kathy graduated from Ben Davis High School in Indianapolis in 1967 and went on to earn a degree in Education from Indiana University. She began her career teaching middle school history in Indianapolis, where her love for learning and storytelling came alive in the classroom. In 1974, she married John Dee and soon devoted her time to raising their two children, Bryan and Megan. Kathy’s love for history and family intertwined beautifully throughout her life. During the cherished annual family vacation to Hatteras Island, NC, she often hosted “Family History Night,” captivating young and old alike with photos, videos and lively storytelling that often ended in a playful quiz. Even the youngest nieces and nephews discovered a love for history through Aunt Kathy’s eyes. Kathy’s strength and grace shone through life’s hardest moments – the loss of her first husband John in 1998 and her son Bryan in 2019. Though her heart ached, their memories guided her, giving her resilience and purpose through the years. In one of life’s beautiful twists of fate, a visit with friends to Alexandria, Virginia, led her to cross paths with Grayson Winterling, who instantly stole her heart. They married in 2002 and built a warm and joyful life together in Easton, Maryland, near his hometown of Cambridge. Kathy was the kind of person who made everyone feel special. She was kind, thoughtful, festive, and faithful – a friend who remembered birthdays, hosted the best parties, and made ordinary days feel like celebrations. She treasured her family and friends deeply, maintaining close bonds from every stage of her life - from college, from her neighborhoods over the years, her “Stranger Family,” and her beloved communities in Easton, Cambridge, and Naples, FL, where she and Grayson spent many happy winters. To her granddaughters, Elizabeth and Sadie, she was their adoring “Grammy,” always ready to FaceTime, laugh, and shower them with love. Kathy also had a special place in her heart for her sweet Golden Retrievers – Shana, Max, Riley, Cody, and Gracey – each a loyal companion who brought her endless joy. Gracey and Grayson were faithfully by her side as she was welcomed into Heaven. Kathy delighted in the simple pleasures of life – a perfectly prepared prime rib dinner, a good bargain on a fun shopping trip, traveling abroad, collecting seashells along the Hatteras and Naples beaches, and hosting joyful gatherings filled with laughter and love. Even after her cancer diagnosis, she faced each day with courage, humor, and unwavering faith, with Grayson’s steadfast love supporting her every step of the way. Kathy’s radiant spirit, generosity, and laughter will be deeply missed by her family and friends. Yet we take comfort in knowing that she is reunited with her Lord and Savior Jesus Christ, and with those she loved so dearly. Her love will remain forever in our hearts. Kathy is survived by her husband Grayson Winterling, her daughter Megan (Kevin) Fisher, of Richmond, KY and two grandchildren, Elizabeth and Sadie. Also surviving are her brother, Ray Clare (Karen) of Carmel, IN; sister-in-law Lynn Dee; stepchildren Stephen (Ingrid) Winterling and their children Will and James, and Jocelyne Winterling; nieces and nephews, Kathleen (Fred) Andres, Chris (Adina) Nolan, Angela (Gabe) Revell, Emily Clare, Wayne Winterling, Donna Ann (Andy Crook) Winterling; and many great nieces and nephews. A Celebration of Life graveside service will be held at 2:00 p.m. on Saturday, November 15, 2025, at Our Lady of Peace Cemetery in Indianapolis, IN, followed by a reception for family and friends at The Bridgewater Club. The family requests that, in lieu of flowers, expressions of sympathy be made to the Irene Nolan Memorial Scholarship, Outer Banks Community Foundation, or PO Box 2299, Manteo, NC 27954. Fellows, Helfenbein & Newnam Funeral Home, Easton, MD, is assisting the family with arrangements.

Kathleen Dee Winterling

September 17, 1949 - October 7, 2025