Seems pretty high compared to what else is out there in this size turn key. There was that 2004 28' Northern Bay with Cummins 220 that was last listed at $39K and that took 8 months to sell. It was also on long island. Maybe this seller bought that boat and looking to dump this?
Seems to be an entirely different mold then the 29, just always thought it would compete with people who want a smaller DE, like the 26 General Marine. But yea, that price difference between 27-29 is tiny.
It ain't worth more than 20k because you will spend 25k-30k on a new motor and gear plus shaft/prop and install and do probably another 5k minimum of other stuff. Unless you can use his non working engine as a core you are looking at being upside down on it if you paid over 20k for the boat.