That would depend on which words you use (as they have different numbers of letters).
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740
Words are considered to be 3-7 characters average. However, normally the 500 characters would include the space between words. Assuming an average for this is 5 characters per word, you could probably get 80-100 words into 500 characters, depending how "big" the words are that you use.
Bout 250
50 words. 5 characters equals one word, so 250 / 5 = 50
there are 24 spaces one for each space and letter on the following words. America's* game*spin$win*