Haven't we seen this before?

I suggest a visit to major paint stores in your area (Sherwin Williams and Benjamin Moore are Houzz favs.) Ask about historic colors and find a color palette that starts with something close to your blue building. They probably have your colors already matched in a nice glossy flyer.

Valspar has historic colors developed in conjunction with the National Trust for Historic Preservation. Start there. But, obviously, that blue is probably not historic.

Your first step is a vist to your historical society to see what colors are appropriate in your area. It takes some planning to make this look right.I have always loved the painted ladies in San Fransico but it depends on your area and the era and IMO you need some interest on that bare wall.

I addition to painting there are other things you can do to bring back some of the historic character of the buildings. Doors of an appropriate style will add more historic character. The commercial entrance on the blue building needs to be more of a feature. One way to do that is to paint the red door to the right of the entrance the same color as the siding so the eye is not drawn to that area.

Kickplates could be added under the windows on building with the purple(ish) door. Since picture windows were on most commercial buildings adding them to these windows would return some of the character of a commercial space.

Awnings could be added over some of the windows.

See if you can find some historic photos of the buildings to see what was there previously. There might have been dentil molding or corbels on the cornice along the top of the blue building that could be recreated.

Signage is another area that can aide in bringing more historic character to a building. Using overhanging signs is appropriate, and also, since the buildings are so close to the street allow people to know who and where a business is.

You need to put together a list of things you want to do and then rank them in order of what has to be done, what you really want to do and finally what would be nice to do but is not a priority. If there is a local Historic Preservation/Planning Department they can be an valuable resource for you. Good luck.

Whatever you do avoid white.https://www.oldhouseguy.com/white-replacement-window/