Very cute house. I personally like as is so if it needs to be redone I’d stick with a light color. I think dark charcoal will close the house up too much. I love how airy and inviting it looks right now.

The other thing you may consider to change up your exterior is to change out the posts and railings. The posts could be beefed up and a new classic, yet modern touch for the railings. Possibly even consider cedar posts instead of painted ones.

I loved the window boxes I had on the front windows of a home I owned in a 6A climate. They also really helped the resale of the house. They will need to be bare in winter, although I put pine boughs on mine. If I were designing yours i would make the box just a bit wider than the bottom sill, with mitered molding on top, and then angled down sides to a bottom that is the same width as the window sill. People often make window boxes too shallow,, which makes it harder for the plants to get enough room for roots, but also looks flimsy and insubtantial aesthetically. I might look for a way to echo the diamond design of your leaded glass in some subtle fashion, and I would be sure that the box coordinated with the look of the door. If you choose a window box it is better to have very low key plantings in bed below. I had compact azeleas.

If you're set on black window frames, i'd suggest painting the shutters a more gentle color. The facade is wide and the windows can benefit from some 'side support' to keep looking well proportioned. Similar with the concrete stepping stones, by the way, great idea just make them wider. And i personally wouldn't keep a red brick patio when all other reds and browns are removed. Your home is totally different from your inspo pic, it will never look that way and that's totally ok as it's a lovely house.