This is something difficult to know. We know from authors like Cicero and Pliny that land could change hands frequently, and that some properties had a great deal of prestige because of past owners (such as Pompey's in Rome). This indicates that land did change hands, and there was nothing particularly shameful in selling it.

This doesn't really answer your question however, and beyond it is kind of hard to know. There have been some very clever attempts to understand changes in ownership from the archeology, a good example being Brobdribb at Shakenoak in Britain, but it is almost impossible to know whether a new wing added on a villa is because of a new owner, or if a lack of change is because the villa stayed in the same hands.