Did you have columns under your roof overhang? I will be anxiously following this thread...because this is my house, lol! And we will be doing an outside reno in the future :).

It does look very similar! No our house never had the columns-there was a short rail along the bottom of the porch (that the previous owner removed).

Nice looking house and adding landscaping is a good idea. I'm not sure if you're considering any structural changes, but you could add some curb appeal by adding a little more dimension to the front of the house. Consider a covered front door or covering a portion of your porch, like you see in this pic (I'm not necessarily recommending this style, just the dimensionality).

I was considering doing this but was worried about the second floor overhang making it not work. May talk to a contractor about adding a small overhang over the front door. Thanks for your comment!

The right contractor should be able to create an overhang for your front door that fits well with the design of the rest of your house. It helps that you have some contrast between the brick and the siding, as there's already a natural break there so the overhang won't be coming out of nowhere. It would definitely add a bit more curb appeal and also make your front entrance more inviting!

Or an awning over the front door? Landscaping (or lack of )is the biggest issue though.

I would consider adding columns to the overhang plus doing a separate covering over the front door. I would also consider removing the shutters since they are too small for the windows. Landscaping will be your friend here.