The house is trying to be a center hall colonial with a 90’s porch and entrance jabbed in the middle. Remove the ‘porch’, remove the giant 90’s window, and install a pair of windows that are the same size as the existing bedroom windows and align with them. Now build a porch that has a roof between the first and second floor.

Thank you! That was definitely one of the options I was considering although I have been unable to find a brick match so I wasn't sure how easily it could be done.

By porch, do you mean something open like this?

I was picturing what housson kindly made- now it looks like a classic American house. If you can’t match the brick you can always paint or lime wash.

I'm wondering how much a makeover like that would cost, ballpark. Seems like it would be quite pricey because you'd have to re build the front part of the roof and re-shingle it all so it doesn't look patchy. Plus paint/limewash the whole house, in addition to the window replacement, new brickwork and building a new porch.

I agree. The only real problem things are the peak and the Columns. The rest of the house is very pretty!!

This is definitely going to be an expensive undertaking although I'd like to avoid it getting any bigger than necessary. We do not have (and cannot easily get) new brick so any changes to the transom window would be very expensive and would required that we paint the brick in order to try to cover the mismatch.

At this point, I've done 3 mockups that would "only" require removing the pitch & columns, replacing the front door (on the plan either way), and possibly adding a portico. We plan to redo the landscaping/front step to something like shown in the 2nd and 3rd pics.

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Thoughts? The complicated part about the portico is that the brick that runs beside the door and around the transom actually sticks out a few inches so we aren't working with a flat surface across the front (thus the angled portico thingy in pic #3).

Paint and landscaping can do a lot. Right now, the things that you don't like are painted white, so they draw attention. Also, there isn't much else to look at besides those white things.

Paint the columns and the gable a dark colour that does not draw the eye. I copied the colour of your garage door. Remove the tall evergreen that blocks your front door, and replace the front door with something more eye-catching. I show a wood one but you could paint your existing door a colour that you like. A deep blue or green would look good with your brick.

Add evergreens to soften the transition from house to lawn, and add some blooms in front of them. Here I show a simple row of dwarf hydrangea.

I like your second mock-up the best. You could use a limestone lintel to replace the transom.