We don’t know, exactly. Oldstones, for example, seems to have remained in ruins ever since the fall of House Mudd, which is kind of odd given that viable land is something of a premium. We also don’t know who the lords of Fairmarket were/are after the Hoares were chucked out. It does seem like a lot of the land between the Red Fork and the Blue Fork is underutilized.
As for Harrenhal, I think it’s a bit of a white elephant thing. If you’re the lord of Harrenhal, so much of your income is tied up with maintenance that you can’t really afford to buy real estate.