I found something entirely different in the symbolism of the chestnut tree:
http://www.symbolic-meanings.com/200...g-of-chestnut/
It is a symbol of foresight.
Foresight, of course, is applicable in Winston's case, because it is the first time he realizes that he is doomed from the start to betray everything that he loves ("I sold you, and you sold me"), which he will echo in the moments before his capture ("We are all dead.").


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