The house is fabulous. I would paint it one monochromatic color- all black, all grey, that sort of thing. Trim on these houses is too skinny to pick out In a contrasting color (the white trim on the windows looks so skimpy right now)

Invest in great landscaping. It’s all this house needs. Right now you have some nice plants but they are all right up against the house as if they are trying to stay warm.

I feel like the peek with garage is too much one all one material. I really like how it’s broken up into different materials on the reference pic. I also love the window above the garage. It makes it so much more interesting. Just worried this look won’t last and my house will be extremely outdated again.

Remove everything colonial- the six panel door, the carriage lanterns, the popcorn ceilings (just guessing). Contemporary design is about clean looks, texture, and materials. Cut down those two conifers next to the house. Stop trying to hide the house generally.

I agree with Hallett you do ralize in the inspo pic that space above the garage is actual living spce not just windows to nwhere which is what you would get. IMO I would satrt with new garage doors for sure and all the overgrowth needs to be gone..You could do something like this if you are not ready to go full on black

Add large corner window above garage, glass/contemporary garage doors, new modern front door, take out three small windows next to front door and make one large one, take out the two very large shrubs/trees against house and trim all others much lower to open the front of house to show off vertical windows. Maybe add a horizonal window above those vertical windows....? I would not go to the expense to raise the roof or change roof line. Adding the natural wood element around your new windows over garage (as your example picture shows) is great looking. Love the neutral white paint as picture shows as well. The brick around garage is a dark grey....but the other brick on right is a neutral tan... Love the tan especially with the neutral white and natural wood feature! You did this yourself, go with the picture!

There is nothing at all wrong with a house clad in a single material. Your house is a good example of late 20th c. contemporary just as it is.

I’m not a fan of “modern”, but that second photo could change my mind a bit. Do you have access to the area above the garage, or would it even be possible to use that space? Would your budget be able to cover the cost of making that space usable?

I am going to throw something out there, and I chose examples far away from the style of your house.

The three buildings in the middle were all modernized during various times because someone decided they looked "dated" The one with the medieval revival peaked roof behind the station wagon was modernized again

They chopped off the gable and put in more modern windows. Granted it is utilitarian, but they were not Trying to make these buildings look ugly, they were "updating them"

This is what one of those houses looks like restored: It's the one on the right side of the empty lot above.

Here's another one. Ignore the blight. The first floor of this building was "modernized" probably in the 1930s or 1940s because the old appearance was "dated". It was restored about 1970

New glass garage doors like in the inspiration photo would spiff up that side of the house. It's an undo-able update, too. No need to cut new windows in the upper area.

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It could be simpler to redo the elevation on the roof over the garage to be closer in its angle to the roofline on the right side of your home and not so much taller. It would still maintain it's midcentury style and be modern as well with your butterfly roof. On the other hand your vertical siding is not doing that tall volume any favors either and a horizontal band of siding could help as well. Replacing your narrow windows with a larger midcentury inspired style as in your inspiration photo (Marvin has this style) and your garage door to coordinate (love the bottom style door) would draw attention to the lower portion of this cool house especially if you remove the obscuring large shrubs. I guess the question is if you try to camouflage that volume, will it give you the result of visually lowering or reducing the slope of that roofline. It might be useful to consult with an architect on this question about whether to embrace or change (lower) the roofline over the garage. This could help you decide where to spend your dollars.

Go full in to the MCM look and embrace what your house is. Great photos being posted for inspiration. Getting a talented architect’s ideas would help you decide.