Ditch the box bay altogether.

From what I am seeing in my computer screen.....

The horizontal brick circled in yellow is a cream. Don't just use any 'ol cream for the garage and windows, color match to the brick. Then take a mid range brick, not the darkest and repaint the brown boxes so they don't stand out so much. Also the stripy gutters.

When I moved into current house I had a 3 year old and one on the way. Landscaping was not on my radar. The front of your house could use some plants. The minimum could be a ground cover perenial that spreads quick and takes little care. With all that brown roof you can't totally get awy from the colour.

if you plan to replace the windows anyway, why not make the window flush to the wall for a more modern look. You could even have a larger window to fill the opening rather than limit yourself to just replacing what you already have.

What is the space on the inside? does it box out making a indent in the room? or it the box window just a decorative box window hanging on the outside of the house?

I agree remove the box jut out if possible . Those are a very dated look and the rest of the house quite nice . Those garage doors are the other dated look on the house so if not replacing please do not bring attention to them with a trim color.

+1 to @toddinmn suggestion. The home will look much more modern with the box bay removed.

I appreciate everyone's input! After we work on the windows in the summer, the plan is to do landscaping in the fall - a lot of love is needed there. While the roof isn't being done immediately, it'll need replacement in the next 3-5 years and we'll probably go with a less brown color.

I would be open to making structural changes to the box window. For those suggesting the box bay be removed, are you suggesting the window becomes flush with the brick / removing the bay window altogether? Or, that the windows become wider (not sure taller is an option based on the inside picture) to fill the remaining space and remove a lot of the exterior wood framing? Or something else altogether? Thanks, again!

Here's a picture of the inside, in case relevant.

I like the boxes. They add interest. I might, however, make the windows wider, so the box frame is narrower. I'd make sure my windows (I'd probably do one per box, not 3 like you have now) matched the color of the box frame. Right now, you have a greenish beige (although maybe that's just my screen) that doesn't go with the brown trim nor the tans or reds in the brick.

" are you suggesting the window becomes flush with the brick / removing the bay window altogether "

Yes, exactly.

I'm in agreement with those who suggest removing the box altogether and making it flush with the brick. It will give you the opportunity to put in much bigger windows.