The house was built in the early/mid 30s by a very affluent family in the area. It stayed in the family until I purchased it. The house is a mix of victorian and craftsman. Most of the interior design elements were "over-the-top" Victorian. The house is the largest/nicest house in the area and is one of the houses everyone knows. There are quite a few things that are not strictly to-code in the house, but the house is grandfathered so most I don't need to worry about. While updating, if it is possible I try to correct any issues, but some things it just isn't possible. FYI, the radiator sits back into the wall under the window. The cubby is 8.5" deep. We've never worried about burning ourselves on that radiator. The one in the basement my knees touch while on the toilet, but they don't get hot enough to actually burn (hot water, not steam). I WILL be fixing that one in the future. I actually found the original blueprints to the house in the basement. From it, I can tell there have been A LOT of changes, and additions to the house over the years. Generally you can look at the material and have a pretty good idea what decade it was done. When I spoke to the previous owner (his father built the house) he told me they didn't care about keeping it era specific or anything, his comment was "we like what we like, and wanted what we wanted", and they had the money to do it... I am NOT a purist, but the bones of this house are of a grand nature. I am trying to restore what I think the house should look like in my own way. I am keeping with the mix of victorian and craftsman as well.

The window trim change would be to Craftsman style. Unless you are doing the work yourself it seems a lot of expense for little difference on upstairs windows. It would, however, be extremely easy to do on your front door as you would only need to change the top board. And you could replace the side lights with solid wood inserts, or you could use textured glass that would obscure the view while still letting light in. While the limestone exterior is very light it has a yellow hue. Simply speaking the easiest way to find colors that work with the warm limestone is to choose a nearby color. That was probably why the trim is green. Since you prefer a modern look, I suggest you keep your siding light and use color only in the trim. Below are two combinations that I like. I darkened the roof color in these pictures.

With the windows and garage doors I would probably go with the same color for the fascia and gutters. I think white siding would look too stark in the gable ends. Something in the taupe family to bridge the dark trim/windows and the lighter brick would look nice. If you're interested in seeing some virtual finishes on your house check out my web site, Creative Visual Concepts.

The colors you are considering are the exact same as our house! Of course elevation is very different - but here is how it looks for reference!