I want to be able to walk around outside and talk hands free (with headphones and built in microphone) and talk on Skype and still have the capability to make phone calls without having to come back inside the house and dial with the computer.

Of course. I’m just the messenger here, so at $164 it’s really pricey.
http://www.skype.com/allfeatures/cordlessphones/

Look around. You may be able to find Skype DECT phones for less.

Carl