I agree with John S. I would add removing the shutters. The windows are not right for them. Otherwise, you have a very attractive house. Good luck!

tight budget and reworking a roofline do not work together.

save up until you have enough money to redo the front how you like.

for now, paint the shutters and concentrate on landscaping. those over grown shrubs aren't doing your house any favors.

Great points! We will definitely redo the landscaping, and I'm on the fence about the shutters. I figured we can try keeping them and reconsider if they don't look right after the brick is painted. The before and after photo that Beth H posted is similar to what I would like to do. Thanks all!

Here’s a late response - just thinking out of the box - could you enclose the porch area (full or semi open) and bring the front door forward? The new entry needn’t be heated, it could be an area to take off boots, umbrellas, dog leashes, hats, etc. I like your new home, lots of charm and character!

I think I would remove the shutters and beef up the trim around the windows.

Meant to add, leave the shutters on smaller windows and add trim work on larger window, like the posted after photo.

Our reno is finished. The budget was busted by having to upgrade all the electric and most of the plumbing. But we did replace the front door and put T&G on the ceiling. Thanks to all for your comments!

Great to see a completed after. Gorgeous. Did not need construction on front. Top off with some pots with seasonal plantings to the porch for some color and interest.

Didn't comment on the original post, but would have said, "Wait until you determine how much money will have to go into issues you don't know about yet like HVAC, plumbing, foundations, etc." I'm glad you got to do some of the things you wanted.