Born in Chatham, Ontario, Fleming painted traditional rural landscapes, Scottish highland scenes, and seascapes set in Ontario, the Netherlands, Wales and England. He also painted many still life in oil and watercolour. Fleming was highly influenced in his early career by the Barbizon school and later progressed in to French Impressionist scientific colour theories which is present in many of his works. By the end of his career, Fleming was influenced by the Group of Seven who were well established in Canada by that time. He exhibited with the RCA (1904-1918) and the AAM in 1909.