To dream that you are homeless indicates that you are feeling powerless and insecure. You are unsure of yourself and where you are headed.
Seeing someone who is homeless in your dream is a reminder to cherish and value what you already have. If you dream that you are mean or cruel to the homeless, then it implies that you are taking what you already have for granted.
To dream that there is a homeless family living in your garage indicates that something is missing in your life. Perhaps you are headed in the wrong direction. Your current path is leaving you unfulfilled and unsatisfied. Alternatively, the dream means that you need to be more resourceful and make the best of an undesirable situation.