Hermann Winter attended secondary school in Wismar and obtained his secondary school leaving certificate in 1914. From April 1 to July 31 of the same year, he completed a traineeship at the castle shipyard in Harburg (Elbe). After the outbreak of the First World War, he volunteered for the Rostock Fusilier Regiment 90. He was deployed to the Reserve Infantry Regiment 210 in November 1914. Severely wounded in Flanders, Winter was appointed as an instructor to the Fusilier Regiment 34 in Krakow near Stettin after his recovery. On December 20, 1917, he volunteered again for pilot training with the Flieger-Ersatzabteilung 2 in Köslin. After receiving his pilot's qualification, he was transferred to the Western Front but never saw action.
During the uprisings during the November Revolution, Hermann Winter was shot in the right upper arm during a battle near Czarnikau, resulting in a lifelong disability and ending his career as a pilot. While in the military hospital, he decided to become an aeronautical engineer and self-taught himself to prepare for his Abitur (university entrance qualification), which he completed on June 24, 1919. He began studying mechanical engineering at the Technical University of Charlottenburg in February 1920.
There, in 1921, he and several fellow students founded the "Berliner Flugwissenschaftliche Vereinigung" (Berlin Aviation Scientific Association), Berlin's first gliding club. One year later, Winter constructed his first glider, the tailless B 1 "Charlotte," with a 15.2-meter wingspan and 100 kilograms empty weight. In 1922, Winter participated in the Third Rhön Competition with this aircraft, but crashed from a height of approximately eight meters on his first flight. The aircraft was rebuilt and given different controls. With the glider, now designated the B 3 "Charlotte II," he competed in the follow-up competition in 1923 and was able to complete several gliding flights. However, Winter collided with a tree during one flight and was slightly injured.
Winter received his diploma in 1924 and subsequently took a position as a senior designer at "Stahlwerk Mark Flugzeugbau" in Breslau. In November of the same year, he moved to Albatros in Berlin-Johannisthal. Just six months later, in 1925, at the request of the Bulgarian government, Winter went to Bozhurishche near Sofia, where, under extremely difficult conditions, he practically founded the Bulgarian State Aviation Industry (DAR) from scratch and designed the country's first own aircraft, such as the DAR-1 trainer aircraft and the DAR-3 reconnaissance aircraft.
In 1929, Winter returned to Germany and joined the Bayerische Flugzeugwerke as a designer. However, he continued to influence DAR designs until 1931. From September 1930 to February 1934, he worked at the Technical University of Danzig at the Department of Aircraft Design. Later, Winter moved to the German Aviation Academy (DVL) in Berlin and, at the end of 1935, to Fieseler in Kassel.
From August 1938 until his retirement, Winter worked at the Technical University of Braunschweig as a professor of aircraft design and head of the Institute of Aircraft Design and Lightweight Construction. There, he also produced several works on various aviation topics, including the STOL aircraft LF1 Zaunkönig.