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As noted in other answers, the Greek ἄνωθεν [anōthen] means either again or above. Since Jesus uses the word twice, each meaning can be applied:

First, Jesus is from above ἄνω [anō] which means from on high or of time, formerly. As with anōthen both meanings apply. Jesus is anō, from above and from before.¹

As noted in other answers, the Greek ἄνωθεν [anōthen] means either again or above. As C.K. Barrett in his commentary states:

ανωθεν is capable of two meanings and here it probably has both. It may mean "from above", but also "afresh", "again". The birth which is required here is certainly a second birth, but it is not (see v. 4) a mere repetition of man's first birth, but a begetting from above, from God.¹

Since Jesus uses the word twice, each meaning can be applied:

First, Jesus is from above ἄνω [anō] which means from on high or of time, formerly. As with anōthen both meanings apply. Jesus is anō, from above and from before.²

As noted in other answers, the Greek ἄνωθεν anōthen means either again or above. Since John records Jesus using the word twice, each meaning can be applied:

See the Kingdom of God - born again
Enter the Kingdom of God - born from above

The response to Nicodemus' question about a man returning to his mother's womb, is "No. For a man to be born again (a second time), requires an act of (re)creation; a man must be born from above (from God)." This sequence follows the central theme of the Prologue:

A person has the authority to become a child of God: they can be born again. This authority is not from earthly rights or privileges. It is from the will of God: they are born from above.

The passage, obviously is understood solely from the Christian perspective. Yet the Gospel indicates a different type of "rebirth" is also possible:

First, Jesus is from above ἄνω. The word anōthen is from ἄνω which means from on high or of time, formerly [anō]. As with anōthen, both meanings are intended. Jesus is anō; He is from above and from before. The others are from below. The word here is κάτω which means below or beneath either of place or temporal succession [katō]. As with anōthen and anō both meanings can be applied. The others have been "reborn" from below:

A person will see the Kingdom of God when they have been reborn, from above or from below:

Seeing the kingdom of God does not mean entrance, because those born from below also see God's Kingdom, but their perspective is negative. In other words, a person who is born from below sees the kingdom of God as something to oppose.

Therefore the complete teaching about rebirth is:

Jesus answered, “Truly, truly, I say to you, unless one is born of water and the Spirit, he cannot enter the kingdom of God. That which is born of the flesh is flesh, and that which is born of the Spirit is spirit. Do not marvel that I said to you, ‘You (plural) must be born from above.’ The wind blows where it wishes, and you hear its sound, but you do not know where it comes from or where it goes. So it is with everyone who is born of the Spirit.” (3:5-8)

Finally, unless one is born of water and of Spirit, they remain as one "born from below" and the second use of anōthen would be "again" not "above".

As noted in other answers, the Greek ἄνωθεν [anōthen] means either again or above. Since Jesus uses the word twice, each meaning can be applied:

A person must be born again to see the Kingdom of God
A person must be born from above to enter the Kingdom of God

This sequence elaborates on the central theme of the Prologue:

A person has the authority to become a child of God. This authority is not from earthly rights or privileges. It is from the will of God. People who become children of God are born again from (God) who is above.

The focal point of Jesus' teaching Nicodemus is rebirth as children of God. Later Jesus teaches there is a different type of rebirth:

First, Jesus is from above ἄνω [anō] which means from on high or of time, formerly. As with anōthen both meanings apply. Jesus is anō, from above and from before.¹

Next, the others are from below. The word here is κάτω which means below or beneath either of place or temporal succession [katō]. As with anōthen and anō both meanings can be applied. The others have been "reborn" from below:

This explains the distinction Jesus made with Nicodemus. There is a difference between seeing and entering the Kingdom of God. Seeing the kingdom of God does not mean entrance, because those who are from below also see the Kingdom of God, but their perspective is negative. It something they oppose:

Therefore the complete teaching to Nicodemus is:

Every person born again [either from above or below] will see the Kingdom of God

Jesus answered, “Truly, truly, I say to you, unless one is born of water and the Spirit, he cannot enter the kingdom of God. That which is born of the flesh is flesh, and that which is born of the Spirit is spirit. Do not marvel that I said to you, ‘You (plural) must be born from above.’ The wind blows where it wishes, and you hear its sound, but you do not know where it comes from or where it goes. So it is with everyone who is born of the Spirit.” (3:5-8)

Only people born of water and Spirit from above will enter the Kingdom of God

Jesus answered, “Truly, truly, I say to you, unless one is born of water and the Spirit, he cannot enter the kingdom of God. That which is born of the flesh is flesh, and that which is born of the Spirit is spirit. Do not marvel that I said to you, ‘You (plural) must be born from above.’ The wind blows where it wishes, and you hear its sound, but you do not know where it comes from or where it goes. So it is with everyone who is born of the Spirit.” (3:5-8)

Jesus answered, “Truly, truly, I say to you, unless one is born of water and the Spirit, he cannot enter the kingdom of God. That which is born of the flesh is flesh, and that which is born of the Spirit is spirit. Do not marvel that I said to you, ‘You (plural) must be born from above.’ The wind blows where it wishes, and you hear its sound, but you do not know where it comes from or where it goes. So it is with everyone who is born of the Spirit.” (3:5-8)

Finally, unless one is born of water and of Spirit, they remain as one "born from below" and the second use of anōthen would be "again" not "above".