Talk to a contractor about what's needed for various window sizes and what the costs will be. In the meantime, take a photo facing the view on the outside, standing close to the outside wall. Print it up the size of your existing windows at a print shop such as Kinkos. Then tape it to the wall to help you decide.

double hungs are easier to dress and would match what you have. save the Big Glass for out the back...

but will you have no walls left? many people like to put even the bottom of a hutch for storage in their dining room.

another thought is a lighter shade of paint, you havent done yourself a favor having so many uninterrupted square feet of something not very reflective. if you end up deciding not to add windows, go with a lighter shade of your grey perhaps.

2 single hungs, no grids

I actually already have my contractor / window guy lined up and invoice in hand, it's just a matter of which window. What you can't see is there is a wall to the left with room for a hutch where do now have a buffet. When we do the kitchen there will be a peninsula on the other side with a dual sided cabinet for things like china etc. Here is a pic of the other side of the room. Again, I am just concerned about the windows not matching being they will same size, etc.

Sliding glass patio door and small deck. Choose wood vertical blinds for the patio door.

Match what is already in the DR

Matching what is already in a room exactly is not necessary.

Those are nice. Why not repeat those?

Thank you everyone for your suggestions. Stengle those do look really nice. Krismays, while I'd love to repeat I am actually looking to open up the house a bit more considering this is a Formal dining room and privacy isn't really we are concerned as in fact I'd love for people. What I didn't mention was on the outside we will be eventually wrapping the front porch around so a bigger window will look better from the exterior with that porch.

If you are wrapping the porch around...french doors would look beautiful :)

I agree with French Doors if you are wrapping your porch around, or at least a single French door. Otherwise, nothing wrong with two single hung windows there.

outshopping422 I couldn't agree more however what you can't tell from the picture is the house and room is fairly small so it might be a bit crowded. House is only 2000 square feet.

Matching what you already have in the dining room would look so pretty. In my opinion the grids would look best since it's the same room. When you do the kitchen, it's technically another room...so no need to match. I love your dining room furniture :)

Thank you. It's from Park Hill and to no surprise after we bought it we have now spotted every item in an episode of Fixer Upper :)