So this is the front of your house? It looks like the back.

I like the idea of continuing the roofline of the sunroom with a pergola, and turning the area underneath into a terrace/patio. That would have the added benefit of partially concealing that one random small window, which isn't centered on anything and looks tiny under those huge second-story windows. Getting rid of the skylight is also a good idea.

I think one of the reasons the exerior is so "unique" is not just the shape, but that there are a lot of different window and door sizes, shapes, and materials going on. Big, small, tall, wide, wood, vinyl. In general, you want only a few different window shapes/sizes on a single facade, and those should all be spec'd the same. I would try to get that to be as cohesive as possible as you replace windows, assuming that's on the docket, and when you paint, I would do all the trim in the same color you paint the siding so you downplay the randomness.

Personally, I wouldn't do two different siding types/styles. You already have enough going on here - it will emphasize that. I'd consider shingles/shakes instead of clapboards. Your house almost has a neo-Victorian/Shingle Style vibe that would make sense with that type of siding.

Having a masonry chimney installed would also do a lot to calm down the uniqueness.

The odd window out is the little double hung window to the left of what I am assuming is the front door? It looks new. Can it be changed out to a casement so that it matches the others? Its proportions and style are wrong. You will unify the house with identical siding and paint. There are some unusual parts to your home. Can you explain what rooms are in them? The tower? The room with the arched window?

Yes the double hung was added over the kitchen sink. The slider opens to the living room. The first floor is basically one big room with kitchen dining and living. Upstairs the tiny window and skylight are the main bedroom, large windows are a common areas, windows on second level of tower are bathroom. Third story of tower is a bedroom.
I agree about replacing kitchen window with a casement. What should we do for the main bedroom? Want to add more windows there - double or triple.
Maybe a matching window to the right of the slider as well, though that will require moving kitchen cabinets….

IMO the hing that is all wrong is the addition upper floor on the right "dormer tower" I agree one type of siding I do not agree that should be shingle but a nice simple horizontol one everywhere would calm down the exterior.I am not sure adding another element to this facade is a good plan so get some good drawings from a good designer to see what will work. Maybe a nice glass roofed pergola type additin very simple no embellishment with curvy rafters .I do not think there is anything Victorian about this home , I would also make that kitchen window larger if at all possible.Once you have done all of that then go to work on some really awesome landscaping that will take you eye off that tower , so lots of color for sure.

This is the type of pergola I was thinking. Hoping to go for a more woodsy modern look, not Victorian. I agree about the tower but there’s not much I can do about it!
Was thinking of a solid body stain on the siding and matching trim color. Should we go with wood tone or a darker color like grey ? Roof will be black.

Still unsure about windows in main bedroom. They can’t be any taller but we could put in a row of two or three.

Something like this for color?

https://pin.it/5TBIAUT