I would remove the overgrown shrub to the right of the front door. The house looks great as is. If you want more emphasis on the front door, you could paint it a deep color (maybe red or blue) and change the hanging light fixture to something more modern looking, that corresponds to your light pole.

I agree that a landscape refresh will be your best bet. The only other thing that stood out to me is the dormer above the entry -- it doesn't look like the window matches the other windows. Lovely home!

I totally agree with einportlander......that window should be replaced.

Have you thought about a roof deck on the flat roof? I wonder if you could change that dormer window so you could exit it and come out onto the "observation deck", and put an interesting modern railing on the edge? the house has a sort of "ship" look about it to me. If you had a railing (like ships railing) it would connect the dormer area to the garage and help visually level out the look. Might want to get some pros out to give you some input and an architect to assess weight considerations, etc. I have a client who took a home similar to this and did some modern touches like this and transformed the home but using "period" type materials and looks. Try talking to your local college professors with knowledge about the architecture of the period and see what you can come up with.

You are talking about drastic changes so you do need an architect. Less drastic changes that would make a lot of improvement would be new landscaping and a different paint color.

I think there is not enough contrast in the gray roof color and the gray house color. It does not appeal to me. I suggest a lighter gray or off white.

The low windows on the front of the house are an important feature and are not meant to be hidden by plants. Really, no window should be hidden by plants.

If you have attic rooms then the dormers need to exist. If they just provide light in a cathedral ceiling then I would remove the one above the front door.

I am not bothered by the flat roof section. Perhaps you just need time to get used to it.

The landscaping (or lack of design) is the only thing wrong with your house. I agree with the advice above re hiring a landscape architect or designer.