Born 1860 in Bradford, England, Winkelmann arrived in New Zealand (Port Chalmers) in October 1878. In 1882 he joined the Bank of New Zealand and worked in branches in New Zealand, Fiji, and Sydney. He began his photographic career in 1892 following his purchase of a Lancaster Instantograph camera but he continued to work for the Bank until 1895.
In 1901 Winkelmann set up his photographic studio in Victoria Arcade, Auckland. His photographs were published in New Zealand periodicals and overseas publications, and in 1895 he won the New Zealand Graphic photographic competition. His most notable overseas award was the grand prix at the Panama-Pacific International Exposition in San Francisco in 1915.
Winkelmann photographed a wide range of topics including well-known individuals and their families and residences, workers and their workplaces, maritime scenes and significant events. In 1928 Winkelmann sold his Auckland city negatives to the Auckland Public Library. His extensive collection of photographs and glass-plate negatives was bequeathed to the Auckland Institute and Museum following his death in 1931.