If so, when?
It would be possible since there has passed all the tests of time. It wouldn't be too hard for it to reach that value since we all know the potential of ethereum. It is just hard to predict when but at least, we have the positive mind towards it and we should hold more for now.
You know one of the proof of reaching the value to $1000 is that we already saw the price of ethereum at $1000 from which we know that it already have a community which will make the value to $1000. When a value is once attained then for the second time it does not becomes hard for the price to reach to $1000.