Toss the shutters and trim out all the windows in a similar style. Why does one have wide white trim?

You desperately need updated landscaping, at least some ornamental trees/shrubs at the corners. It looks like there are some small green things lining the foundation but whatever they are they’re not particularly eyecatching. What’s your planting zone?

We are zone 5b. The small green shrubs lining the foundation are rose bushes. We don’t like them. We have no idea why the previous owners did the wide, white trim around the window. My guess is they were trying to give it some character.

Paint the white trim to match the rest of the trim and spend your money on landscaping. The house is great, does not need "jazz"

Does it need a new roof? I feel like the shingle and brick are not easy companions, could just be my monitor.

With those dark trimmed out windows it appears someone already 'updated'. You just need to get them all matching including I am seeing three different colors on the trim out. Go with the darkest if on trend is your goal.

These comments are all so very helpful. Thank you for all of your thoughtful responses. I now have some really good ideas to explore!