Windows would be beautiful flanking the fireplace. Before doing that project, though, you might consider whether or not the dark brown couches are affecting the light in the space. The reason I say this is that I once tried dark brown slipcovers on our old white couches, and found that they sucked the light out of our low light living room. I didn't realize how much those white couches were doing for the space until I covered them in brown. It would be interesting to put a light color, maybe sheets, over the couches and see how it changes the perception of light. Although, with the prices of furniture today, new windows might be cheaper than different couches!

This is obviously an outside wall and you might want to carefully check into how much wall space you will actually have once you come in from the corner for house frame and window frame and in from the fireplace for the same thing. You may be left with very skinny windows and then you have to decide if that is what you are envisioning.

If that is a problem and in the interest of maintaining proportion you could put smaller square windows on either side of the fireplace above the mantel height. Like the first picture here windows by fireplace

Does the four-season room run right to the end of the fireplace wall or can you put a window in the wall where the tv is located.

Something else to consider is how about a mirror over the couch and using reflected light as a way of brightening up the room. Instead of a table lamp you could also put pole lamps in the two corners and so bring the light up into the ceiling where there are probably shadows.

Anyway, random thoughts as you could probably tell.

My concern with putting your TV over the fireplace is that it will be too high and everyone will end up with sore necks, unless you lower the height of the surround. That, and the fact that people sitting on the couch against the wall will have to look sideways.

I like the idea of windows but also fear there is not enough space and two skinny windows will look odd.

Agree that perhaps lighter furniture and some mirrors would help.

I'm assuming there is a second floor above the family room. Otherwise, I would suggest a skylight or a solar tube.

I agree with laughablemoments - furnishings can make a huge difference. A light area rug and lighter sofas could make the world of difference. I've done that in my dark-ish living room - off-white "fun fur" covered loveseat, with light tan leather easy chairs, and a light patterned area rug. Another good suggestion: a mirror opposite the "window" would help a lot. I would be concerned about whether windows might look awkward on the fireplace wall.

We put a light-ish rug on top of our dark LR floors and what a difference it made! Much lighter, even with the dark brown sofa and medium-dark wood furniture.

High windows would look very nice on either side of the chimney and bring in light and open feel, even if you can't really enjoy the view, and even with a sheer-ish blind if it gets too bright (which direction does that wall face?). The TV could go on the wall below them at a comfortable height.

The windows would face north (indirect light), so bringing in extra light with mirrors and light furnishings combined with windows are great ideas. I agree with all the concern over the size of the windows. This is important, it needs to look right, so..

What would be the best approach tackling a project that involves placing windows into a exterior brick wall and possibly remodeling the fireplace for the best overall function and look? I'm not sure what professional we should be working with….we've talked to a contractor who can do the work but not the design, we've talked to 2 interior decorators/designers who do not have experience with this type of project...I'm not sure that a window company could manage the design…a design architect? I know different companies can get the job done, but we're looking for experience and knowledge in this area-windows and fireplace.

Since most of the light from windows comes from the top, you could put in short windows with cabinetry underneath including a spot for the TV.

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If you didn't want to go through the expense and process of adding windows, you can get the same impression with glass fronted lit cabinetry.

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Your room reminds me a lot of our family/living room (just the one room in our small house). Similar paint color, dark room, white fireplace, tv vying with fireplace for focal point... The only windows in our space are in the corner to the right of the fireplace, they are adjacent to each other. The one by the fireplace faces East, and the one adjacent faces South but is shaded by our patio. They are on the taller side, 72" tall but 31" wide; evenso, we really don't get much light except in the early part of the day due to the orientation.

I don't know the best approach for you to add in the windows, but IMHO east or north-facing windows aren't going to bring in that much extra light except in the morning...although it sounds like they will offer a nice view (we don't even have that going for us LOL). Do you spend a lot of time in there in the morning?

Have you considered just embracing the fact that it's a dark, cozy room for enjoying a fire and watching a show? Is a four-seasons room a sun room? Maybe that can be your light/bright space and this room can be your rich, vibrant-color, cozy space.

I think it would be helpful for you to solve the room layout issues first, so that you can prioritize with respect to budgeting and remodeling.

One thing that would make decorating a lot easier would be to combine the TV and fireplace into a focal point. That would be a great focal point since the entrance faces that wall. Then you can orient furniture around that focal point, and create some pleasing symmetry.

Realistically, how much is the room used for TV watching? Is it 20% or 90%? If it's a high number, then IMHO it would be worth decorating around comfortable TV watching. I don't know what the best solution is but you don't appear to have a lot of wall space suitable for the TV (the wall opposite the sun room would be glare-y.

I have a crazy idea. Mount a mirror TV over the fireplace with a drop-down mount. The mirror in the photo below is actually a TV - crazy huh? Available in various frame styles and sizes.

Samsung LED Mirror TV

And use a down-mount like this so that you can view TV at a comfortable height.

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I assume all that would be expensive, but seems like it would solve a lot of problems? At the same time you could build in some storage on either side of the fireplace to deal with the inevitable media gadgets and clutter.

Perhaps a "tree" like the one in the Comfortvu photo above would add some life and texture as well.

Some of the fireplace-flanking window photos in previous posts look really nice, but they all appear to be on much larger walls than yours? Dimensions and proportions are going to be critical.

I'd lighten the room with a light area rug, lighter pillows, slipcover the ottoman in a lighter fabric, and, though it might seem counter-intuitive, darken the stain on the TV cabinet. A darker cabinet will balance the heaviness of the sofas.
Either that, or make the room more clubby with deep toned walls.