The words bailey, bailee, bailie sound the same but have different meanings and spellings. Why do bailey, bailee, bailie sound the same even though they are completely different words?
The answer is simple: bailey, bailee, bailie are homophones of the English language.
A person to whom property is bailed.
The outer wall of a castle.
The space enclosed by this outer wall.
A Scottish municipal officer corresponding to an English alderman.
Obsolete A bailiff.
Definitions from The American Heritage® Dictionary of the English Language, 4th Edition and Wordnik.
Homophones (literally "same sound") are usually defined as words that share the same pronunciation, regardless of how they are spelled.