Usually means: Most dilapidated, shabby, or neglected.
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We found 12 dictionaries that define the word dumpiest:

General (10 matching dictionaries)
  1. dumpiest: Merriam-Webster
  2. dumpiest: Oxford Learner's Dictionaries
  3. dumpiest: Collins English Dictionary
  4. dumpiest: Vocabulary.com
  5. dumpiest: Cambridge Advanced Learner's Dictionary
  6. dumpiest: Wiktionary
  7. Dumpiest, dumpiest: Dictionary.com
  8. dumpiest: Cambridge Essential American English Dictionary
  9. dumpiest: FreeDictionary.org
  10. dumpiest: TheFreeDictionary.com

Computing (1 matching dictionary)
  1. dumpiest: Encyclopedia

Slang (1 matching dictionary)
  1. dumpiest: Urban Dictionary

(Note: See dumpy as well.)

Definitions from Wiktionary (dumpy)

adjective:  Short and thick; stout or stocky.
noun:  A short, stout person or animal, especially one of a breed of very short-legged chickens.
noun:  (South Africa) A small bottle of beer.
adjective:  Of or relating to a garbage dump; rubbishy.
noun:  (slang) Synonym of dump truck (“prominent buttocks”).
noun:  (surveying) Ellipsis of dumpy level. [(surveying) A level having a short telescope, usually an inverting one, rigidly fixed to a table capable only of rotatory movement in a horizontal plane.]
▸ Also see dumpy


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