The earliest I found was from Amsterdam in 1695.
This 1712 edition, also from Amsterdam, has a beautiful woodcut of Jerusalem that looks like it is based on the 1695 one but with much more detail:
Here's a 1716 edition, from Rabbi Aharon ben Uri Lipman:
There was a 1744 Haggadah whose woodcut that was identical to the Lipman one.
The Jerusalem depiction in this 1746 is almost an exact mirror image of the 1695 one:
The one picture of the Temple that most interests me is this one, from 1738 and also from Amsterdam, but with a much different woodcut:
No one has ever depicted the Temple as an octagon.
But, perhaps, the artist was not depicting the previous Temple - but a future one. (The last three words on the top margin, "וכן יהי רצון", would seem to indicate that.) And if that is so, it seems possible that he had heard about the majestic, octagonal Dome of the Rock on the Temple Mount which is at the exact spot of the two Temples - and thought that the new Temple could be built using its walls!
