New windows! The windows (and shutters) look worse than the siding. Will be worth every penny.

Agree with above, make the windows as large as the whole brick inset space, lose the inset shutters.

looks like someone took out a door at some point and put in that window. That's why you have that mish-mash look. Did you guys do that? That should have been addressed at the time.

why do both windows have that little step out porch? what used to be there? doors?

the shutters do not fit and don't belong there w/those short windows.

best thing to do is call in a mason guy and see what he says. I'd put in larger windows and have the brick redone so that it comes up to the window. (no shutters) mason should be able to match the bricks.

+1 to millworkman comment above. They did you a bit of a solid by not bringing the brick up. Much easier to enlarge the opening at that point.

We bought this with hopes to change it in our future. We found some house plans close to original when we moved in. They had tiny windows in it too. Maybe changed minds as they built or to cut costs. The opening is HUGE! More than a standard door but not enough as a patio. Do not want doors there like I said kids rooms. The stoop as someone saw is actually egress window covers. They can hold in case of fire. Was thinking a large double hung with maybe a window with a transom window above that to add length. I don’t know how big I can go since bedrooms are 11’ wide on window wall.

Once you decide you'll get new windows (let's say 4 or 5ft wide) and new siding, you could fill out the 'cavities' around the windows. Also remove the concrete coins and have some nice paving along the windows.

Then again, I like the brick. If it were mine I'd probably fit the windows in the inset's width and add horizontal siding under it, same as on the side of the house.

I certainly would not be spending money replacing brick with siding unless there is some problem with the brick Those windows need replacing anyway if they are in kids rooms since they are not egree windows. They are a decent width so just get new windows that fit that width but are bigger in length then that piece at the bottom will be quite small and paint it to match the brick or better yet get some brick to match no matter what those shutters need to go.

The existence of the brick "window sill" tells me the window was meant to be full length. Forgive the crude image, like this. Imagine both panes the same size, I am not good at images.

Some houses were built like this with built in shutters. I think if you remove the shutters you will find there is no brick beneath.

You could make the window less expensive by leaving the top part stationary.

If you remove the shutters and use siding it will be more like this.

From the street it will still look like shutters.