I think that some fairly inexpensive things could make a dramatic difference. First I would replace the iron columns with some more substantial 6x6 supports (with some moldings perhaps) and add some railings. Also, I would not paint the porch, but stain it. I think taking out the concrete porch would be a very big project. I would also add railings and wider wooden steps to the front door. Paint or replace the front door for pop and in your individual taste. The shutters look out of place and out of scale for the picture window. Shutters should look as if they would actually work, these do not. Once this is done the right of your house would be heavy and you would need to balance this out with a nice curved bed on the left with a fairly large tree to add balance. Zone 5 maybe a nice magnolia. Fill in the large bed around the tree with some nice plantings. Towards the road cries out for a small fence with a gate or maybe some hedges with more beds. A flagstone path up to the front steps. A small tree (maybe a Japanese maple) on the right and curved beds along the walkway and driveway. I think this would take your home from plain to fantastic with the least cost and with things that you can probably do on your own. I am sure you can. I do like the idea of shutters, but think you should look at different sizes and styles. I don't like being critical, however I think that by asking for help you are probably looking for honest evaluation.

A definite YES to the new porch column and railing. If your porch is less than 30" from the ground you shouldn't even need a railing although it may be your preference to have one anyway. Do like the idea of a garage door with a glazing (glass) in it somewhere. Perhaps the whole door could be glass? Good Luck!

(no, none of those your mentioned would clash w/your windows. I've linked quite a few articles for you to read. give them a shot first, and then come back if you have questions) Here's a color review on Dorian Gray. she favors Pure White and High Reflective white for the trim. https://www.kylieminteriors.ca/paint-colour-review-sherwin-williams-dorian-gray-sw-7017/ Have you ever read any of Kylies articles on exposure and paint colors? very interesting. here are a few you can peruse https://www.kylieminteriors.ca/exterior-painting-4-things-to-know-before-picking-a-colour/ https://www.kylieminteriors.ca/the-best-exterior-paint-colours-why-your-homes-exposure-matters/ scroll down to where she talks about East facing homes. SO, HOW DOES EAST-FACING LIGHT AFFECT PAINT COLOURS ON THE EXTERIOR OF A HOME? East-facing morning light is bright and will make paint colours look MUCH lighter than they will in the afternoon An east-facing afternoon will look an AWFUL lot like a north-facing one in that it gets NO sunshine and no shadows. It’s also similar to a west-facing morning light – flatter than a pancake In the afternoon, east-facing homes can look more shaded – more like they do on the north-facing side (or western morning) With east-facing light being tricky, you’ll want to pay attention to the LRV that you choose. This way, you can land on an LRV that doesn’t wash-out too much in the morning, but also doesn’t look too heavy in the afternoon. https://www.kylieminteriors.ca/paint-colours-and-lrv-the-ultimate-guide-to-choosing-the-right-colour/ https://www.kylieminteriors.ca/how-to-pick-exterior-paint-colours-in-5-easy-steps/ https://www.kylieminteriors.ca/sherwin-williams-best-gray-greige-paint-colours/ this link is all gray paint colors that she talks about. pay attention to the undertones and the LRV https://www.kylieminteriors.ca/page/2/?s=gray+exterior+colors

Okay, thanks All. You've talked me off the painted woodwork cliff. Appreciate the great suggestions! Oh I'm so glad to hear. In reality, if and when you go to sell, you truly would lose the majority of those who love old homes with the gorgeous woodwork. I know I was looking for a craftsman home in my area for over 2 years. Yes there are plenty that were built here in the 20's. However each one I went in had been remuddled. Either by adding on without thought, or painting old growth woodwork, or changing gorgeous old floors to put down tile (we're in FL) or a number of other things. In every case I could tell from what era they had remuddled the house based on what was in it. If they had worked instead with the house, even with necessary updates, I wouldn't have been the wiser. Make sure the next owner of the house isn't the wiser. :) I would also look online for old issues of Victorian Homes magazine. (Not sure they exist anymore). I would also look into Bradbury and Bradbury wallpapers as they specialize in patterns for Victorian homes.