While the description says up to 26 inch monitors, would it be possible to have three 27 inch monitors with the center one in landscape and the other two in portrait?

That should be fine. If the vesta holes are the same which I'm sure they are it will work.

I know it technically says up to 26", but could it hold three 27" in landscape?

If you look at the literature on the Ergotech website holds 3 - 27" wide monitors.

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Ergotech 100-D16-B03-TW Triple LCD Desk Stand

Out of Stock