Yiddish is infamous for its vocabulary that draws on both European and Middle-Eastern languages. It is therefore no surprise that there are in Yiddish, one from Hebrew and the other from German.
In my dialect (Southern/Galician Yiddish): דורך is pronounced "derekh." But wait: so is דרך (literally meaning "way"), such as in דרך־ארץ, loosely translated as "respect." Of course, this couldn't cause that much ambiguity, considering that the first is a preposition and the second is a noun. But how about this one (it's very witty, actually): .עמלק and אַמאָליק
Don't be fooled by the disparity in appearance. They are pronounced almost exactly the same. One is amolek, the sworn enemies of the Jews who attacked them from the back in the desert. Haman from the Purim story, and, more recently, Adolf Hitler, are said to be spiritual or physical descendants of amolek. The second word is amolik, the adjective meaning once-upon-a-time. Can anyone think of a sentence where the meaning would be ambiguous?