If you cut just the top, yes it should. if you cut it too low it can end up killing the tree though. Cut just as much as you need to, it will grow back.
It generally will, but it does depend on the age of the tree and how wide the trunk is where the cut is made. If the trunk is only a few inches, then another top should appear in time.
The top will never grow back to its origional look. It will grow weaker shoots that tend to break off and become very weak. Tree topping should never be preformed.
The Leland Cypress is a beautiful tree. It has two diversions. If you want to cut the tree firstly clip the same one. Then say to neighbour cut their side and on the same way we have to cut. This helps to growing of the tree.