if I apprehend (yet another!) David's question correctly, he seeks not words that can be defined in two nearly opposite senses (self-contradicting, enantiodromic)*, but rather words such as those in column one of the "cabbage puzzle"--non-selfdescriptive (heterological) words; e.g., monosyllabic, adjective.

one of my favorite words which exhibits this quality is orthoepy, which has the meaning "the customary pronunciation of words"; orthoepy has two accepted pronunciations.

*self-contradicting words have been discussed in these pages to some degree in the past.

(for that matter, heterological words have come up in a couple of threads, notably this one: http://wordsmith.org/board/showflat.pl?Cat=&Board=words&Number=6120)