That's an attractive traditional house. Pick up a Sherwin Williams paint deck, it will save you time and trips. The brown roof looks different in the two photos. Try a peachy off white or pinkish off white depending on the dominant color of the front facade's bricks. Also, put Samplize samples next to the pinkish brick on the front since that is the most important area to coordinate.

IMO the biggest update would be new windows and landscaping. As for paint gutters should be the same color as the roof and painted downspout to match the siding In this casea color from the stone for the siding and yoou could keep the white trim since I assume new windows are not in the budget.and thay are white.If my any chance those Xs in the lower windows can be removed do that to see how much better it looks.

I'd do cream for the trim. You could consider a warm blue or olive for the siding, but a tan or brown from your stone might work, too.

No one can comment on your landscaping when the pictures are in shade. Is it lovely or in desperate need of improvement? I certainly can't tell.