I'll be watching to see what others say. I have a similar situation with sidelights on either side & above the door. My thought is to paint the door a very dark greyish olive (same color as exterior), leave the rest of the woodwork white, & paint one wall (the one that goes up the staircase) a light-to-medium grey green to soften the contrast & make the eye flow up the stairs & to the back of the hall - hopefully tying the whole thing together. I've already painted the back hall door (double lights in door but no sidelights) a medium-dark green (from same color card) & left the trim white but haven't gotten the nerve to attack the front entrance yet.

@Windows on WashingtonLtd and @grafefruit1_ar Ideas on layout of new windows? Stick with casements? Double hung? The large front window is one large framed opening with a double casement, a picture window, a double casement. The sections on either side of the fixed section look different because of window screens. Here's a close up: Altogether it's about 10.5' x 5' of single pane steel casement loveliness *insert eye roll*. You both make a good point about vinyl. When we bought our home 21 years ago, there was no vinyl that would have looked nice enough to use on the front of the house. The choices were pretty much Anderson or Marvin wood windows. Vinyl has come such a long way in terms of both quality and looks. The contractor that did all the windows also built our great deck, and helped us remodel our family room: contacted him about our current kitchen remodel. We had a good conversation about it and asked me to email him the plans. I did. Never heard back. Called and texted again, never heard back :-( Very disappointed. Thank you for your feedback

Leave the interior of both doors the same color as trim in house. Just paint the exteriors black, and your choice if you want to paint both of them.

The door and sidelights should all be painted the same color. Be sure to sand and use a quality oil/solvent based primer. I really like Fine Paints of Europe for entry doors. Be sure to use their recommended primer too. It really stands up to weather and time if done properly. Love the high gloss finish too.