If you are going to square those off, I'd make sure that all of the arched windows are addressed. The easiest thing would be to fill in the arches and build the opening down, but it might leave the proportions looking weird. Those rough openings are square, so you could bust them open and square off to the full height as well.

The only other thing that I'd say is to really think about if you want to get rid of them. Styles and trends are a funny thing, where the latest and greatest fad today is garish tomorrow, and some of those things come full circle. In my years around homes, what I've noticed is that things that design trends that show quality, craftsmanship, and generally cost more come back around even if they go through a period where the fashionistas say that they are terrible. Style trends that are cheaper but just happen to be "current" are the ones that don't age well. I'd put arched top windows into the former category, especially on a home like yours. Its part of the design. The irony of course is that the same design crowd that will tell you that you MUST get rid of the round top windows were the same guys and gals making these designs 20 years ago, and are often the same that will lose their minds if you were to suggest altering the shape of a round top on a turn of the century home that is half the size and value. Square them off if you want, it will make your home look more "up to date", but it will also cheapen the look and detract in the long run IMO. Just my $.02

Cheaper to move.

^^^Lol @Joseph Corlett, LLC... although if this theme of updating the window openings were to be applied to the entire home (bringing it into the "20's" style-wise), that point probably has some merit.

As far as the windows themselves, I'd either keep as is or blow them open to the full RO -- if there is clearance to do so on the inside. We[ve done this on a couple homes recently, although they were all siding, no brick.

I'm glad the OP is worried about the changes looking strange. That's encouraging.

I never decided these were great so I would square them off but it will not be cheap since the brick makes this an expensive proposition. Since it looks like you have siding at the entry that window will be the least expensive to change to a rectangular window . I think the others will require siding in the gables to make it work and a really good exterior designer to make it look intensional. IMO those windows do nothing for the house but neither did all the gables.

Redo the one over the door and the tiny tiny one on the former. The other ones will be costly!! Because you’ll need a pretty skilled mason to fill the gaps. To me the thick border seems to be the issue more than the arched windows. I’d try to thin out the trim around the windows and repaint. I don’t mind the round at all

*Dormer

Save your money for fixing the leaks in the roof. What a flashing NIGHTMARE. SOMEONE always graduates at the bottom of the class. Even architects.

Thank you for the suggestions everyone. I purchased this house in the condition that it is. I also do not care for the gray frames around the windows or the gray doors. I intend to paint the door black, put in black windows and white trim. I would love to put in a portico but I’m not sure if that is in my budget since I also need to replace all of the siding. Unfortunately, it is rotting. This house was purchased knowing it was going to be a project that would require a significant facelift. I also don’t care for all the gables but that’s certainly not a change my budget.

Thank you ourfarmhouse for your rendering! That is incredibly helpful to see!!

Thankfully the roof was replaced six months before I bought the home.

Sure thing.

Sometimes the best way to tackle this is over time. Of course, doing the windows at the same time as the siding would be a good idea. It is the best way to make sure that everything is water tight. Other projects (like a portico:) can be done at a later date...when you have lived with the changes for a while AND when you have recouped cash:) Good luck with your project!!

ah, yes. The farmhouse look. I'd give that fad another 5 years tops. And not that there is anything wrong with farm houses, they are great, but I puke in my mouth every time someone tries to make their home that is clearly NOT a farm house, look like a farmhouse.

#freethepallets

I'd just paint a lighter colored trim around the windows so they aren't such a focal point, and leave them as they are. Paint the door a brighter color.