[5] In 2015, Kerber Verlag published a large monograph of Winter's work to mark 20 years of painting in Germany titled "Dizzyland.

In particular motifs from Obersalzberg, Hitler's Berghof and the surrounding mountains are integrated into Winter's large-scale works on canvas.

[10][11][12] His series of paintings "Virgin Forest" (2005) exhibited in New York at Salander O’Reilly Gallery (and years later at Frances Lehman Loeb Art Center at Vassar College) is based on the comparison of English and German fairy tales set deep in the woods.

[18] Winter's series "Weird Science" and "Unnatural History" deal with human longing to transcend the ordinary through magic.

[19] In his series "Speculative Realism", Winter extends space and reality, combining the installation with figurative and abstract painting.

[8] In 2007, Winter was the first of five artists chosen to exhibit in the project "DRIVE THRU Gallery" in Aschersleben, Germany, initiated by the Bauhaus Museum, Dessau and Internationale Bauausstellung.

In vacant lots huge reproductions were placed of paintings by Christopher Winter, closing the gaps between buildings creating an oversized gallery exhibition in a public space.

Artists such as Julian Rosefeldt; Jonathan Meese; Elmgreen & Dragset; Andy Hope 1930; Gary Hill; Jonas Burgert; Martin Eder; Daniele Buetti; Julien Charrière and Assume Vivid Astro Focus were exhibited.

[27] In September 2016, Winter curated “"A New Language" for the Contemporary Arts Festival ROOT 1066 in celebration of 950 years since the Norman Conquest.