Keep the stucco, definitely - yeah it does require some occasional maintenance every ... oh, half a century or so... but it really is a quality item. Either patch and repaint, but make it an earthier color that realates better to roof and brick chimney - eg if green, a browner/richer/earthier shade of green. Or if you are resurfacing entire house, they can color the stucco itself to leave you with a more maintenance free surface that has a more of a natural masonry pebbly surface that can be VERY attractive. Im curious do you know what the original color or finish was? Not that you have to replicate it, but it can be helpful to inform you what the original intention was and look up pictures of other stucco houses of that era - could be Im way off about my inclination toward earthier colors for stucco. Your houses era/style, midcentury modern, is very fashionable these days and in fact a lot of contemporary architecture and home furnishings replicate or are inspired by that era.... so you really cant go wrong by remaining true to that style. You say "modernize" but IMHO, getting houses back to their roots and making changes that are harmonious with and true to the original design esthetic is usually the best choice. That in itself will make your house look totally refreshed and "new." Actually I cant see any sign of swirl marks in the photo - I don't think changing that would have nearly as much impact as repairing the surface & refreshing the color. BTW, I do agree with above posters that it is a very attractive house as is!

I was going to say, just take it off the dang thing and replace with siding. Its just a veneer and often only on the one side of the house, not relating to anything else. Then do raised beds and stairway in stone in front to ground the house and give appearance of solidity. Create a good size landing in front of the door - at least 3-4 feet out, with the 4 steps going down between the raised beds on either side. The beds should extend at least 6 feet out to allow for a generous display of perennials or flowering shrubs. If room add small ornamental tree closer to the street, to the side of the house. Oh well, a project for another time maybe. IMHO small modest houses always benefit from lush cottagey plantings - - you could get geeky and choose popular 1950s era flowers like bright zinnias and red carnations

That extension of the small sidewalk on what would be the side of the house was what I originally meant about putting in a concrete sidewalk. Although it would be nice to change the location of the entryway unless the entryway on the front of the house was changed to a window vs. simply being bricked up it would probably cause people to think subconsciously that there was something missing and therefore wrong with the house. One thing about extending the original front entry with a much larger stoop is that there is what appears to be a window to the basement. While it may not be a problem now and there may be other windows our current codes require an easily accessed egress window if there is any living area in basements. The steps coming down from the sunroom although they fit the area appear to be too steep for comfort. It is a personal preference of mine that I like to have a step wide enough that my whole foot is on it when I step onto it. Since you are thinking of things that could be redone perhaps a decorative ramp could be used in place of those steps for entry onto a patio. That could assist if anyone would have a health problem like a broken leg that would make using stairs a problem. The a/c could be moved but if the house is like many of this same age with addons there may be spots that are not evenly cooled. It might be possible that there should be two units. My house is of a similar age and this is one of the things I am currently exploring if I decide to stay here.

Definitely not gray with a tan roof. When you say ’flat roof’ you don’t mean removing the whole roof and its pitch, do you? In my experience, flat roofs always leak because they don’t drain off. I’d see if I could get the rocks and chimney the same color as the siding/stucco (or whatever the body of the house is). If you stay with the current roof color or go to a tan, make the rest of the house a pale tan or cream or beige.