That is not easy, but you can store the image url of the enumeration image in an attribute (you can find the url by inspecting the images in a datagrid), and show them using the dynamic image viewer.
I want to use it in combination with the Countries module. The images use a two-character country code but the enumeration does not.
A decade down the road there still no option to show an enumeration’s image in a template grid (or list view). Two widgets help, but each require you to manually fill a list connecting the enum-values to the image, which is a manual action and maintenance issue. Adding a new value to the enum, requires you to also add the new value to the list.
Workaround I used is adding all the enumeration’s images to the page and set visibility to the related enum-value.