The cheap one is the Pro model. What this means is that it's built with a higher clamping force. This can have dramatic effects on both the comfort and sound as it pushes the drivers closer to your ears and can feel like a vice on your head.
Also, judging from the picture, that is the old revision of the DT990s. You can tell from the different grille design on the earcups. The newer ones (post-2005 I believe) come with the silver slat grille design. It's actually remarkable that Amazon even has "new" old revision DT990s for sale. They haven't made that design in years.
If you're willing to consider different impedances and buying a used pair, you can get them around $230 on Amazon right now. Their Amazon Warehouse deals are typically brand new open box items that got returned for stupid reasons and they have Amazon's full 30-day money back guarantee if you decide you don't like them.