Andersen sells their window paint colors. Spray can is, like, $30. I'd seriously consider the Terratone option because 30% is a lot. Spray paint the two windows to match - do it now. While you're involved in the window thing. Don't put it off and then one day find out mis-matched windows could hurt resale and then you end up having to paint them anyway. Plus, if it were my house it'd bug me if they didn't all match. Get the new windows (I think a darker tone will look better than white) and then choose a paint color. It's a lot of color area. The good news is with a dark brown roof, trim, terratone windows you have A LOT of options for body color. Might want to start with your favorite color (not blue)because you truly have many color options. After new windows and paint maybe take a look at updating the landscaping. At that point you may feel it's far more attractive than you thought with character to spare. Just color can do that.

@HALLETT & Co. Great answer, thanks! We'd love for the whole house to be a different color, but don't have the budget for it right now. So maybe we could replace the trim when that project comes up. The quality of work on the remodel is mixed and we'll be steadily improving it. @toddinmn Yes, I started off looking at painting the trim, but then got more and more bothered by the style once I got into choosing a color. Skimming the trim smooth sounds appealing, but stucco is so strong, that I can't picture it coming off to leave a smooth surface! What do you mean by "venerating"? I tried looking that up but couldn't find anything. @chiflipper I was looking at a mossy green for the trim, actually. Funny you should mention the ironwork because that's my favorite thing about the house! But thanks for the input. I'll think about it. :)

The fact that there were no leaks is ONLY attributable to the lack of rain this this case. Is that small vinyl accessory piece on the exterior applied with a kind of stick'em tape? I would see about removing that and having some site fabricated flashing installed to tie if back to the building and sealed to the sheathing. At that point, the stucco can be re-done and if you want it to die right into the window, you are going to need to push the window out or fabricate some sort of exterior jamb to return the stucco to.

Hi. I'm no expert (very far from it lol), but in dealing with a situation similar to yours, I came across this video: https://www.youtube.com/watch?v=kUXKXJScyYQ This person added the trim afterwards (on top of the stucco). Doing that might make you feel better about your windows. Good luck going forward. Please let us know what you decided to do. Depending on the shape of the trim you choose, if you try this, you might be able to get close to the look of the window trim in the picture shared by Jeffrey above even though not actually recessed.