Extreme homonyms

While not antonymic, several have unrelated meanings.

Note: Several of these words, while spelled the same, differentiate meaning by having different pronunciations.

homonyms but not homophones

• Tear - The liquid that flows out of a sad eye or a rip or breach in something, especially cloth.

• Lead - The metal which alchymists attempted to turn into gold or the action of offering direction, or the person who performs that function, if used as a noun as in "This teller is the lead."

• Wound - An injury to a person or animal or the action of turning or winding something in the past (he wound the watch.)

• Wind The movement of air or the action of turning or winding something.

homonyms and homophones

• Groom - a man about to be married or the person who cares for horses.

• Lie - To deceive by telling an untruth or to rest one's body horizontally such that it is not supported by the feet.

• Duck a quacking bird which waddles on webbed feet or the action of bending one's self (duck your head.)

• box a cuboid container or a martial sport of fisticuffs.

One of my favourite incongruous pairings is cleave (to split) and cleave (to stick together).

I can literally only think of one (or two):

Literally - used to emphasize the truth and accuracy of a statement or description that is actually true - Factual.

Literally - used in an exaggerated way to emphasize a statement or description that is not actually true (or possible) - Figurative.

First example: I got into a cab and the driver took it literally when asked to go straight across the traffic circle.

Second example: Of course, we got into a wreck! From that moment on, our worlds have literally been turned upside down.

This wasn't always possible until a few years ago when the figurative meaning of the word was added to the dictionary - due to its overuse (and misuse).

According to the dictionary, “literally” now also means “figuratively”