Robert “Bert” Winslow passed away in the comfort of his home in Dunnellon, Florida, on June 1, 2026, following a courageous battle with cancer.

Born to Cecil and Elizabeth (Lewis) Winslow in Boothbay Harbor, Maine, on Sept. 23, 1937, Bert was a 1955 graduate of Boothbay Region High School. He proudly served his country for four years as a member of the United States Navy. Following his military service, Bert dedicated his professional life to the community he loved, serving as the East Boothbay Postmaster for 25 years before retiring in 1992.

Bert found peace and joy on the waters surrounding his home, where he loved to sail. He also enjoyed golfing with friends, hunting, and fishing.

He was predeceased by his parents; his first wife, Ruth Hartford; his daughter, Jennifer Winslow; and his brother, Herbert Winslow.

He is survived by his loving wife of 34 years, Confetti Winslow; his daughter, Kate Winslow; his stepson, Treb Iman, and his wife, Iris, and their daughter, Camilla; granddaughters Hannah Winslow and her husband, Jude Alamo, Jessica Winslow, Holly Walton, and Madison Stilkey; and his nieces and nephews, Allen Winslow and his wife, Debra, Laurie Taylor and her husband, Steve, Kim Meservey and her husband, Mike, Scott Winslow, and Darren Winslow and his wife, Kate. He is also survived by his great-grandchildren and extended family.

A private ceremony will be held in the fall.

In lieu of flowers, the family requests that donations be made in Bert’s honor to the United Methodist Church of Boothbay Harbor.