looks more like late 40s or mid fifties to me. Cute home.

1939!

What grapefruit said. Especially the shutters and the tall shrubs at the front door. BeGone!!

Do you really need an awning there? It looks like a secondary door and I assume you'll probably enter the house through the garage.

@benjesbride, it will be a very often used door as only one of the garage doors is functioning (cabinets and a utility room of sorts were built on the right side of the garage), but a rain deflector on the roof might work. That thing just screams dental office to me!!

Littlebug and grapefruit, I also thought about the tall things! That front door won’t be used as often, thankfully, but they need to go! I’d like to incorporate some tropical plants here and there to break up the wall of evergreen that surrounds the house.

I'd want to see what water does in that area -- you have an overhang and shouldn't need the awning, but there's an odd set of angles meeting up, and maybe something unfortunate happens, like rain from the garage roof corner spraying the door area. If it's not strictly useful, i'd get rid of it and not replace. If it is solving some problem, then I'd look for a more pleasant solution, one that doesn't block the door and maybe stands out less as well.

All of the above and how about something like this instead of the awning you have.