Carl Alexander von Winkler was born in Tallinn in 1860. He graduated from the Dome School of Tallinn in 1879 and from the Faculty of Philology of University of Tartu in 1884. At the same time he studied drawing under Rudolf Julius von zur Mühlen in Tartu.
As an artist he improved his skills under the tutelage of the landscape and marine artist Hermann Eschke in Berlin, Germany and took watercolor classes with the English artist Charles Jones Way in Lausanne, Switzerland. In the years 1884-91, 1897 and 1901-1907 he lived and traveled in many places all over Europe: Germany, Austria, Switzerland, France, Italy, Croatia and Norway. He also traveled frequently to St. Petersburg, where he took his drawing teacher exam in 1892.
Winkler was an esteemed artist who gave many exhibitions(incl. Tallinn, Tartu, Pärnu, Rakvere, Riga, Jelgava, Dresden, Munich, Berlin, St. Petersburg) and whose works were gladly obtained. The bigger part of his creative works is comprised of Estonian, Italian and German landscapes and cityscapes, his watercolors are especially esteemed. Since 1904 he was a member of the Watercolorists’ Union of Munich .
Winkler died in Dresden in 1911, he was buried at the Mõigu Cemetery(which was destroyed in the 1950s).