Yes you can over hunt an area.
Will I still do it, yes I am going back into an area this weekend but I only do this because I hunt public land. The pressure is constant and constantly moving the deer. If you own your own land I would think it depends on how much property you got available. Smaller 10-20 acres would move around the property a bit and give it rests in between so you dont push all deer off your property. If your lucky with a larger tract 100 plus I would continue hunting it just moving around the property if you notice changes in the deer movements.