A native of Sindi, Estonia, he was born in 1892 and spent his early years as a mate on a variety of American and British ships, an experience that intensified his appreciation for marine scenery and ways of life. Following his seafaring career, Winter became a US citizen in 1921 and enrolled at the National Academy of Design. He continued his artistic studies in 1925 on a traveling scholarship to Paris and Rome.

Winter exhibited extensively from the 1920s until the 1950s, consistently earning medals and awards, and became a member of numerous artistic societies, including the National Academy, the Salmagundi Club and the American Watercolor Society. Winter's work can be found in major public and private collections throughout the United States, including the High Museum of Art, Atlanta, the Toledo Art Museum, the Portland Museum of Art and the Farnsworth Library and Art Museum, Rockland, Maine.

After spending a number of years summering on Monhegan Island, Winter and his wife and fellow artist, Mary Taylor, settled there as year-round residents in 1940. Winter built a studio on a bluff overlooking the ocean, where he found a constant source of inspiration in the remote and rugged scenery of the island and its inhabitants. His often dramatic renderings represent Winter’s incomparable ability to transmit to the viewer his fascination and understanding of rugged island life and the many faces of the ocean.