Rupert Winters Fennell

Rupert Winters Fennell, 80, passed away peacefully at his home in Spencertown, New York, on April 21, 2026, with his son Simon by his side.

Born in 1945 in New York City to Thomas Francis Fennell and Theresa Winters Fennell, Rupert was the second youngest of 5 children. He lived a long and full life marked by quiet strength, dedication, and deep care for those closest to him.

Rupert attended St. Ignatius Loyola before graduating from St. David’s School, where he was guided by his mentor and lifelong friend, David Hume. He went on to attend New York University as a freshman before transferring to Syracuse University, where he studied art history and graduated cum laude. He later earned his master’s degree in art history, furthering his studies in Florence, Italy—an experience that deepened his lifelong appreciation for art and culture.

Returning to New York, Rupert entered the Parke Bernet (later Sotheby’s) training program, beginning what would become a distinguished career in the art world. Over the next 27 years with Parke Bernet, and then Sotheby’s, Rupert served as an expert in the English Furniture Department before going on to help lead the Estates and Appraisals Departmentm first in Los Angeles, and then eventually back to New York, where he concluded his career with the firm.

While at Sotheby’s, Rupert met his best friend and the love of his life, Charlotte Jane Davy. They were married in New York City on December 15, 1973. Soon after, the couple moved to Los Angeles, where they welcomed their son, Simon, in 1976. In 1986, the family returned to New York City. Following his years at Sotheby’s, Rupert moved to Spencertown, New York, where the family had long maintained a beloved weekend home.

While living in Spencertown, Rupert worked with Colin Stair at Stair Galleries in Hudson, New York, and also ran his own appraisal business. He retired from the art world in 2015 to spend more time with his family, his garden, and his books.

Rupert was a loving husband, a dedicated father, a beloved little brother, and a loyal friend. He had a passion for history, his garden, good debates, and, as anyone who knew him would say, a good dinner party.

He will be remembered for his impeachable character, his wit, his terrible puns, and the warmth he extended to those fortunate enough to know him. Rupert carried himself with a steady presence that brought comfort and joy to family and friends alike, leaving a lasting imprint on all who crossed his path.

He was predeceased by his beloved wife, Charlotte Jane Davy Fennell, and is survived by his son, Simon; his brothers, Dan and John; and countless nieces and nephews.

A memorial service will be held at St. Peter's Presbyterian Church in Spencertown, NY, on June 26th at 3:00 PM, followed by a reception at the Spencertown Academy. Arrangments entrusted to Robert M. Donaghue of French, Gifford, Preiter & Blasl Funeral Home.