JetMaxx, since you are feeding the deer in your yard and the area you describe is residential these deer may not be hunted much or at all. Combine that with being fed by people and watched often, deer will lose their fear of humans.

In areas of CT and around Philly that I know of deer can seem almost domesticated they live so closely with people. I wouldn't push this guy to much as deer have been known to rush people and from the behavior you describe he could be a prime candidate.