B-2 Visa, re-entry (with existing ESTA)

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So, if I don't leave the US, I can stay until april 21, 2016 without having an overstay, correct?

Yes. The valid dates of your visa (up to December 24th, 2015) is the date up to which you can enter the US. Upon entry, your stamp will tell you the date that you are to leave by.

What is, if I leave the US. I have to visit my family for Christmas and like to come back in January 2016, would this be possible?

Not with your current visa, since it expires in December.

Another question: I already have an existing ESTA which I used for entering the US in 2014. Saying, I could not re-enter the US with my B2 visa after december 24th, could I enter the US with my approved ESTA?

Yes, your ESTA remains valid after your visa expires (as long as your passport also remains valid).

Is all this somehow affected by the fact, that I take part in the greencard lottery?

No. You may enter the greencard lottery at any time, even if you hold other visas or are actually in the US.

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