Usually means: A significant amount of money.
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We found 5 dictionaries that define the word pretty penny:

General (4 matching dictionaries)
  1. pretty penny: Wiktionary
  2. pretty penny: Dictionary.com
  3. Pretty Penny: Wikipedia, the Free Encyclopedia
  4. pretty penny: TheFreeDictionary.com

Slang (1 matching dictionary)
  1. pretty penny: Urban Dictionary

Definitions from Wiktionary (pretty penny)

noun:  (idiomatic, informal) Chiefly preceded by a: a considerable amount of money; a high income or price.

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