Is there a second story above this room?

@jck910, yes there is a second story above

OK I was going to suggest skylights

A question for the professionals...would transom lighting work in this space?

You understand the amount of work involved, no? Workers will have to remove the finish on the outside of your home down to the foundation as well as inside your house - even if your desired window isnt that large. If you have a brick or stucco home - that means removal of such in the shape of your window but extended all the way to the ground. Further, electricians may have to come in and move electrical if you have plugs. A support frame has to be built. Food for thought, take the price of your desired window and triple it. Is that what kind of a price point youre looking to spend? Windows are cheap; the labor and finishing work are a long road to whats in your imagination.

Instead, maybe consider hiring an electrician and install recessed lighting.

Yes we never use this room because it is so dark and it’s our family room. We would like more natural light for our long winter months in New England since we love the room otherwise and it’s the place we should be spending most of our time.

We have vinyl siding and had it priced out before. Just wondering design advice.

If you have the budget, I think I would have the fireplace centered and create symmetrical windows on either side. If your fireplace is a gas insert, it can usually be moved without moving the exterior chimney. However, probably that whole wall will need pretty significant construction to put in windows anyway.

Do you recommend this type of window