Words

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The longest common word
"pneumonoultramicroscopicsilicovolcanoconiosis" (45)6
The two longest one-syllable words in English
"screeched" (9)2, "strengths" (9)2.
words which contain all five (or six, if you append "ly") vowels in alphabetical order
"facetious"1, "abstemious"4, "annelidous"5, "arsenious"4
words which contain all five vowels in reverse alphabetical order
"duoliteral"5, "subcontinental"5 "uncomplimentary"5
words which contain the longest strings of consonants14
"bergschrund" (6), "borschts" (6), "eschscholtzia" (6), "latchstring" (6), "weltschmerz" (6)
longest word with no repeated letters
"uncopyrightable" (15)4
sentence containing seven spellings of the [i] ("ee") sound
"He believed Caesar could see people seizing the seas."
sentence containing nine ways the combination "ough" can be pronounced
"A rough-coated, dough-faced, thoughtful ploughmanstrode through the streets of Scarborough;after falling into a slough,he coughed and hiccoughed."
longest word typeable on a qwerty keyboard with left hand9
"desegregated" (12), "desegregates" (12), "reverberated" (12), "reverberates" (12), "stewardesses" (12), "watercresses" (12)
longest word typeable on a qwerty keyboard with right hand10
"homophony" (9), "homophyly" (9), "nonillion" (9), "pollinium" (9), "polyonomy" (9), "polyphony" (9)
longest word typeable on a qwerty keyboard with alternating hands11
"dismantlement" (13)
longest word typeable on a qwerty keyboard on the top row ("qwertyuiop")7
"rupturewort" (11)
longest word typeable on a qwerty keyboard on the middle row ("asdfghjkl")8
"alfalfas" (11), "hadassah" (11)

Semantics

words with two synonyms which are antonyms
"cleave" ("adhere" and "separate")4

"cover" ("conceal" and "expose")13

"sanction" ("approve" and "prohibit" (colloquial))12

"transparent" ("hidden" (jargon) and "known" (jargon))15

"trim" ("garnish" and "prune")16
seemingly contradictory synonyms
"flammable" and "inflammable""toxicant" and "intoxicant"