Sure, dark windows. No shutters on the rightmost window, for sure, maybe the rest too. Serious need for some kind of landscaping!!

I actually think the current roof colour looks fine as is but black also good.

I find sometimes the black windows particularly if they have cross pieces look like lego windows and draw the eye to the window frame when it's in large contrast to the colour of the side of the house (though you have shutters). I don't really think window frames are that interesting so I don't like them as focal points so I would think twice about black.

It's quite an attractive house and you get in some plants it will really help.

I think in terms of curb appeal one of the big issues is the hard to locate front door. I think a bigger landing would help perhaps something that would result in a large landing when you come out door into the yard and then wraps somewhat to the left [in picture] of the door. Or perhaps a portico or your porch may do this too depending on what you were envisioning.

Where were you thinking of putting the porch?

Some pics to show you what I mean (but I'm not suggesting the walk way materials shown in the photos)

I agree with acm.

I think a charcoal roof with black windows would look good.

Be careful about pressure washing the limestone. I believe it is a relatively soft material. Look for products made for washing stone.

It would be nice if you could widen the stoop and frame the front door. I don't know how you would add a porch, since the existing roof pitch is so low.

The biggest bang for you buck is landscaping. Plant for a couple of native trees out in the yard. Layer plantings along the foundation with all material spaced at least a foot away from the side of the house when the plants reach maturity. Look for a variety of leaf color and texture and add perennials to the mix.

Good luck!

Thank you guys! Yes some plants and shrubs will look great. My porch idea without understanding structure would be adding a gable over the front large window and door. Create a walkway into the yard to the middle of the decking. Just keeping the weird door on the corner.