Asymmetrical windows are tough, but a portico entry might help.

Paint shutters black & put nice window boxes (Walpole)under windows

I have a very similar house & want to do what a neighbor did. Adding doggie dormers made a huge difference. Agree about adding portico

I think you are on the right track, focusing on landscape and hardscape. The walk to the front door could use a redesign.
yes, the upper windows are not true colonial/ don't balance with the lower story, but you have a lovely lot, and found a house that says home to many people. Reminds me of my mom's home.
Focus on the entry. And leading guests to the entry in a gentle and pleasant way.
congratulations on your new home.

And, obviously, that tree planted too close to the foundation, next to the entry, has to go....

Raegan Ford thank you for your constructive comments. I also am putting on a new roof - what color would go with a white exterior and black shutters? Black? dark gray? Thank you again,

I also agree with a nice portico and walk. When choosing a roof color, you might want to research the energy efficiency of dark roofs in your area; they can absorb heat.

I LOVE the current siding and colors, it seems totally appropriate for the house. a new roof, walkway and landscaping is all it needs. Personally I don't think dormers would look good in that house at all.

Laura, I think a medium gray roof would be perfect. The roof color in the attached photo is neutral, not too dark and would look good with black shutters...and lots of other colors.

Your double windows are really too large for shutters. A wide trim around them would be better...and maybe add the window boxes mentioned.

Porticooo

A portico under that upstairs window that doesn't align with the entry below it will be a nightmare. I would remove all the faux shutters and beef up the window trim. Paint the house a great sage green or a blue to fit in with your wooded lot. Aluminum colored metal roof.

The overhanging second story makes it a Garrison Colonial, if you want to search Google for what other people have done with theirs. I agree with no dormers and no portico. Looks good as it is.

If the taller evergreen is a yew, you an trim it to just about any shape. For example, you could clip it to a classic triangular shape and with a bit of clipping every year, keep it like that. I think it looks good where it is now. If it's not a yew, pruning is less likely to be successful.

A larger front light would look good. If you have plants in pots, or if you plant annuals in between or in front of your shrubs, choose red ones to echo the front door color.

The existing gray roof color works well. Nice house.

I was going to suggest a metal roof and a front porch addition:

I think you have the perfect house to put on a front porch

But here is one w/a portico

and a close up view of one in the construction phase. Also, notice the black metal roof.

metal roof on white house. great investment if you're going to be in the house a long time

Partim thank you for the info that the house is a garrison colonial. You can bet I’ve been all over Google with that one. But - What could the builder have been thinking with those asymmetrical windows on the second floor?!?

The comments I have received here have been extremely helpful. Thanks to everyone.

I will post “after” pictures, probably in the spring.

(I’m about to undertake a massive reno of the interior, also.)

If you search for Garrison Colonial here on Houzz and you find one with a portico, you'll note that it aligns with the door and a window directly above. Consider moving the window or the door to achieve that balance. Reducing the size of the window above the door might be achievable depending on what room is behind your upstairs window. I think a porch will block a lot of light from your interior first floor.

I assume that the asymmetrical windows relate the needs of the rooms in the house. Changing them would probably require an interior renovation and some major expenditure. I wouldn't obsess about it. It's a lovely home. Actually quite a few of the garrison colonials that I saw online had asymmetrical windows, so it's not unusual.

I would do the porch straight across like Beth suggested.

Laura, any chance you have updated photos to share? We have a similar garrison colonial situation (right down to the asymmetrical window/door situation!), and would love to see what you ended up design-wise. In the process of planning new siding, and portico addition.