With a hip roof you can only extend the clerestory windows between those two points.

Thank you!

Have you considered skylights on the back roof where they won't show from the front?

This might help you:

Making Shed Dormers Work - Fine Homebuilding

Also, see this for what not to do.

McMansions 101: Dormers | McMansion Hell

I would not mess with that adorable house. I would relandscape first, then replace front door with an all glass version. Lastly, would love to see pictures of inside of your living room because I bet there are some decorating tips that would really help lighten up your space.

Logical first step would be to replace the front door with a full or 3/4 lite door. The roof pitch is so low that I have my doubts about a shed dormer looking good or even being doable.

Shallow dormers all the way across like Beverly shows will really change the character of your house. Skylights make more sense, and would be considerably less expensive. You certainly need to refresh your landscaping so the bushes aren't as tall, and changing the front door is a good idea. Which direction does the front of the house face? I agree with Jeanne, can you show us the room? Maybe people can make other suggestions for brightening it up.

Older homes like this rarely have more than a single central light fixture in a room. Start with the outside landscaping, but put a better lighting plan on your radar as well. Yes, people DO turn on lights in the middle of the day if they need them. The new LED lights are super energy efficient, so it is not going to result in a big utility bill.

Adding interior living room photos from the initial real estate listing. We have since painted the room SW Alabaster, which helped brighten the space a bit.

Thanks to each of you who took the time to offer your thoughtful ideas. We do plan to thoroughly relandscape, replacing the leggy azaleas with fresh ones (and other native beauties), and to replace the front door with a full glass one. I love that so many of you suggested these too! (Simplynatural, your visual on that is beautiful!) To answer kandrewspa's question-- the house faces north/northeast and the home is surrounded by tall pines, so the front never gets blasted by direct sunlight, making that room fairly dark all day. We can absolutely improve the interior lighting, and will address that when we get to the renovation of that room. I also want to dig deeper into the option of raising or vaulting the ceiling (currently 8 ft), as I know that would provide more light and airiness-- we were told that there is so much HVAC duct work in the shallow attic that vaulting was not an option, but I can get a second opinion. I mostly wanted your opinions on whether a dormer would blend with the style and character of our home, but it sounds like wisdom says it would not-- I really do appreciate your thoughts and opinions!

Charming house. Often contractor speak ‘not an option’ means ‘more money than we think you want to spend.’ Vaulting that ceiling means structural engineer, framing changes, all new ductwork, and possibly new hvac as well. So much money. Could be great but seems like maybe too much? Have to agree with Minardi- this house needs some recessed lights. 9 4” recessed cans 30” from the outside wall would be transformative. Also re the azaleas- if you plan to replant them just cut them down to a foot tall this fall, they will fill right back in. (I hate azaleas but I know they are beloved by many)

Glad you painted the room a light color. Your floors look like they need refinishing. I would go as light as possible with them as medium to dark floors really suck up the light. And obviously keep window coverings totally open during the day. Light rug and furniture, colorful art also. And maybe think about taking out a couple of the tall pines you say are blocking the light.

Accept the house you chose to buy, as is. The big structural changes in ceiling height and roofline that you want to make would be probably 60-70% of tearing the house down and starting over.

And NEVER remove a mature azalea. Merely trim them back after the bloom, in order to be more manageable.

Remove the bushes in front and I have no idea how adding something with a roof could possibly add more lighting inside . Do some nice landscaping thta does not block the windows at all and a new front door with som e glass in a nice bright color would be awesome.