3 Jesus answered and said to him, “Truly, truly I say to you, unless someone is born from above/again, he is not able to perceive the kingdom of God.” 4 Nicodemus says to him, “How is a man, being old, able to be born? Is he not able to enter a second time into his mother’s womb and be born?” 5 Jesus answered, “Truly, truly I say to you, unless someone is born from water and spirit/wind, he is not able to enter into the Kingdom of God. 6 What has been born from the flesh is flesh, and what has been born from the spirit/wind is spirit/wind. 7 Don’t marvel because I said to you ‘You must be born from above/again.’ 8 The spirit/wind blows where it will and you hear its sound, but you don’t know where it comes from and where it goes. So it is with everyone who is born from the spirit/wind.
The Greek word for “from above” is ἄνωθεν. It can also mean “again”. ἄνωθεν is used 5 times in the Gospel of John. The 3 times it is used outside of the above passage, ἄνωθεν means “above”. See John 3:31, 19:11, 19:23. Since 3:31 is actually part of the above passage, then one can see the use. Verse 31 begins “Ο ἄνωθεν ἐρχόμενος ἐπάνω πάντων ἐστίν” (The one who comes from above is over all things). The main Greek word for “again” is πάλιν. John uses it 45 times in the Gospel. So, there is no confusion about the words. John uses the word to create the confusion in Jesus’ and Nicodemus’ conversation. Jesus means “from above” while Nicodemus is thinking of the alternate meaning; “again”. That’s what prompts his questions. In his 2nd question in verse 4, the Greek word for “not” here is μὴ. When μὴ is used with questions, a negative or “no” answer is expected. There are two words for “not”. οὐ with questions expects a positive or “yes” answer, while μὴ expects the “no” answer.
The problem with translating ἄνωθεν as either “from above” or “again” misses the word play in the Greek, but there is no equivalent English word that will do the job! The really fun thing about this is that Jesus and Nicodemus would not have had this conversation in Greek! They would have had the conversation in Aramaic. So, John is probably doing this in a stylistic way.
The other word play is with τὸ πνεῦμα (spirit or wind). There is another word for wind which is ἄνεμος and John uses it in 6:18. So, he is using πνεῦμα for wind on purpose here in this passage as he is aware of the other Greek word for wind. The verb form of πνεῦμα is πνέω and it means “to blow”. John uses it here and in 6:18.
Finally, what are to make of these word plays? John either used them as a matter of style or used them to draw attention to what was being written. I tend to lean toward the latter and will add that John’s Gospel was written to be read in Greek and not in any other language as a translation just doesn’t do the passages (at least this one) justice.