This is a portrait of a young woman sitting on a low wall with the out of focus tower of a castle in the background which I believe is Kenilworth Castle. Admittedly, I can't be sure it is Kenilworth, but since one of the Challenge photos was identified yesterday, and this picture was in the same box, I'm reasonably certain.
I would guess that his picture was taken sometime in the 1950s judging by the hairstyle the woman has, and the clothes she is wearing.