Tudorizing it all the way, including the brick and appropriate muntins and mullions, is certainly one approach in creating character that is sorely missing. The original style is mid-century modern gobbled by gables. In any case, minimize the garage with hardware and paint that makes it appear to be two doors.

I'm not a fan of painting brick as it turns a no maintenance product into a long term maintenance issue. The brick seems to have more browns than grays in it but the roof is gray. You need to find a color that marries the two. Something in the taupe family would work. Also, a couple of other things. If you plan on keeping shutters I would switch to a wider shutter that is correctly sized for you windows. The current ones are too narrow. Also, the area without a railing in front of the door needs to have one installed. Building codes require them if the change in elevation is more than 30", which yours definitely is. If you're interested in seeing some virtual makeovers of your house check out my website, Creative Visual Concepts.

Thanks very much! I accidentally included pictures that showed the front of the house before we replaced the kitchen window and added a window to the left of the front door. The quick background is we renovated the kitchen during quarantine (because that is a fun project to take on with working remotely full time in IT and having kids at home 24/7 :)) and as part of that project we replaced the double casement kitchen window with one that has a larger, fixed center flanked by casement windows on each side. We took the old kitchen window and added it to the bedroom that is to the left of the front door. Previously, there was no window on that wall. This seemed like a no brainer at the time because the wall to the left of the door was begging for a window. We also ended up adding a 4 ft. by 5 ft. double casement window to a wall in the master bedroom that looks out onto the backyard. Against my better judgement I ordered the same window for a smaller bedroom that has the same orientation to the backyard as the master bedroom. My hesitation in ordering it was that this bedroom is smaller and has french doors that open onto our back patio, and I suspected the window was going to be too large for the room. Once it arrived, it was clear that I had made a mistake. However, I had an aha moment when I realized it would be perfect in the front bedroom (to the left of the front door). If you are reading along at home and shaking your head, I UNDERSTAND! SO! The window by the front door will be replaced with the new window. May I claim quarantine craziness?! I swear I'm usually much better at executing on projects.

Glass would be an interesting way to go. There are many options, but something directly above the door is far preferable to extending the roof. And getting water off will be important. I don't think an architect is necessary and it would be difficult to find someone who would take on such a small job. But it DOES need to be engineered. Maybe start with a local contractor but make sure it will be properly supported and drained.