How in-your-face?the new property is newer and the entry points much more in-your-face.
How visible? How large a box could you have? Would an outside socket make sense there?
Any quality enclosure with cables taken in through the bottom will be waterproof.
If a socket would make sense you could fit a 2-gang Masterseal with a cable coming out of the house and up into the bottom of the enclosure, and the SWA running from there to the garage.