For this ongoing series on Top eBay Chess Items by Price, my favorite items are paintings or other artwork, because they are usually unique pieces. (The previous art post, Top eBay Chess Item Twins, was an exception, for reasons unknown.) The painting pictured below, titled 'Eugene Ansen Hofmann Large Original Oil Painting on Canvas "The Chess Game"', sold for $1355, 'Buy It Now'.
The description said,
Well listed artist with auction results to $28,000. Frame Dimensions: 30" x 42". Image Dimensions: 23" x 35". Signed lower left. In original frame. Frame is near perfect. Painting has minor cracquelure. Two very minor areas of paint loss. Each is approx 1/8". Overall, in beautiful condition for its age. I am not an art expert and am describing this to the best of my ability.
I found another chess painting by the same artist (but without cherubs) at Worthopedia™: Signed Ansen Hoffman (LR) oil on board, which gave some further information about the artist.
Eugene Ansen Hoffman is a German artist best known for his genre scenes and interiors. (b.1892 - d.1955).
Besides chess and interiors, he also appears to have been a specialist in nudes. I imagine that's the type of piece that sold for $28.000. As for Worthopedia™, a 'Value It' query on 'chess' returned 'Found 87,895 sold items'. That's a lot of chess items and might be worth a longer visit.