Is it somebody enormously wealthy like Bill Gates (who, even though he's not from Massachusetts, is the largest private owner of land in the country)? I actually thought that the largest landowner in Massachusetts was New England Patriots owner Robert Kraft, but no, that wasn't correct, either. I'll grant you that he's probably the most famous person from Massachusetts(at least nowadays), but he's not the largest landowner. According to the World Population Review, the largest landowner in Massachusetts is the company W.D. Now, if anyone asks you who the largest landowner in Massachusetts is, you'll know the answer!