[1] Winterfeldt was born in Berlin and received his commission as an officer in 1888 after attending the Prussian Staff College.

After the outbreak of World War I, Winterfeldt left Paris in August 1914 to serve as quartermaster to the 8th Army, with the rank of Oberst.

From August 1917 to November 1918, he was representative of the Supreme Army Command to the Chancellor, with the rank of Generalmajor.

[2] In November 1918, Winterfeldt was a delegate to the armistice negotiations between Germany and the Allied Powers, led by Matthias Erzberger, minister without portfolio.

With him, Alfred von Oberndorff of the Foreign Ministry, and Captain Vanselow of the navy, Winterfeldt was one of the four German signatories to the Armistice of 11 November 1918, which ended the hostilities of the war.