Hope your post will get noticed by groveraxle.

It would help if you posted actual photos of your house (though the aerial view is helpful too)

Ah, sorry! Here's a front view of it! That dormer will be shifted over and will look more like the dormer on the inspiration photo above, and the whole thing is getting resided (that siding is past retirement age!).

Two years ago we looked into turning our third floor attic with good head room even without dormers into a master suite. Due to the age of our English cottage the floor joists were not to present code for the weight of adding a living area and bath the estimated cost to finish the space was close to 200k for an added 740 sq ft. Without even touching the existing roof line. We desided to build a small addition Next to our existing bedroom for a fraction of the cost. Talk to contractors and architects to get a cost idea.

@Sophie Wheeler and @roarah - Thank you for your kind and helpful input! To give a little background, we've been working with a residential designer and contractors for about a year and a half, and right now we're actually working with a full roof raise plan - so yep, joists will be sistered, electrical will be upgraded, stairs are actually ok, foundation is good, we will zone HVAC, electrical will be upgraded. Right now, we're looking at 180k for the full roof raise project (bidded by several firms). We looked at other iterations with dormers on the back, but never with moving the dormer to the left (Sophie, I know it's not technically shifting, but yes, it would be rebuilt). The front could never be broken into two separate spaces because of the centering of that window. I'm talking with my residential designer now about how this plan might possibly lower the budget - I have to imagine there's some possibility that using the existing roofline and enhancing it might be less costly than taking the house down to the second story floor joists and rebuilding it back up - which is the present plan!

Where are you located? Because that seems really low for the overall scope of a tearoff and rebuild of a second floor. Really low.

I think the house will suffer with an off center dormer. Especially since you are not counterbalancing that with an added mass of an addition below. The reason the inspiration works is because it has balance, not symmetry. And it is much wider than yours.

I would just eliminate the center dormer window in order to partition the space. But, at the present size those windows do not meet emergency escape requirements for bedrooms, which is a must.

I am located just outside of Milwaukee, Wisconsin.

It may be that you're right; that's why we're just exploring the option with my residential designer, but I wanted to bring some ideas to him if people in the internet world have them.

Eliminating the center dormer altogether could be an option, and is not one I had thought of. It would be too bad to have a room with only the window(s) on the side of the house (which do meet emergency escape requirements), and to have such a "roof heavy" front of the house. I hate the way the front looks at present, but the dormer at least breaks up SOME of the long roof line. (Maybe I hate it mostly because my house is yellow and brown!)

And when you say off balance, do you mean because our house doesn't have that other little peak over the stairwell? I'd actually be open to doing something like that, I like it. But again, it remains to be seen if it would work. According to the website I got that photo from (they do bungalow plans), that inspiration house is 5 feet wider than my house is.

Off balance because you don't take an old craftsman house and put a pop top on it. That's called remuddling. Your house is nothing like your inspiration. In fact your house is so much better, but if you remuddle it, it won't be. (Not that that house is bad. It's not!)

99% of people, including house "designers" (in most cases glorified draftsmen) haven't a clue what makes a craftsman house so wonderful and how to keep the character.

I hate the way the front looks at present,

Your front just needs the siding that is not authentic to it removed, the proper siding replaced if needed, replacing the columns to hold up the porch roof and a proper paint job to bring it back to its craftsman roots.

First do some research by going to your local historical society to see what the house looked like when it was new.

If you want to do it right, forget the designer and find an architect who understands this style of house. I would suggest in this case you get in touch with David Heide as one suggestion. You need an architect. Not a designer for something this extensive. Otherwise it's going to look like a b*st*rdized version of what it should be.

I would also suggest you join this Facebook group. It's all about American bungalows.

No, don’t eliminate the dormer. Eliminate the Center window in the dormer. You will have to recreate everything anyway with a reframe. Reframe it with two separate windows instead of 3. With enough space between them to fit the 4 1/2” of a wall and drywall, plus a skosh. Yes that makes for awkward window treatments other than doing inside mount blinds. But it preserves a great deal of charm and originality in appearance. If you choose the correct type of windows. That’s the obvious solution. So I wonder why your drafter has not suggested it.

I really think you need an actual architect rather than a drafter with a fancy unregulated title.

@cpartist which Facebook group? I don't see a link.

Without an architect, this could be a disaster. Please do as the above posts advise and keep us informed!

A designer and a contractor are only good after you have met and figured out what is possible and that requires an architect and maybe a structural engineer.What you are planning where i live would be 200k and up. Your inspiration would require a new house it will not work with yours.