re: The Crag?
I suspect that this is 'The Craig' on the St. Jude's Road, about a mile south of Andreas village.
According to Sally McCambridges's book 'Andreas' (2005): Thomas Saile [modern spelling Sayle] is recorded as the owner of East Craig [the modern name for the property] in 1727. The Corlett family eventually came into possession of East Craig in 1837, then the Teare's in 1924