The joys of home ownership :) You don't have to tear up the stucco. Here is a good method. Get a diamond blade for your circular saw. Get an expensive high quality one. On the outside, right NEXT to the exposed aluminum frame, cut through the stucco AND the nailing fin. Experiment with your blade depth because you don't want to be cutting into the stud. Diamond blades don't work so well on wood! Be careful on the corners to get a full cut - you'll have to go past 3/4" to compensate for the circular shape of the blade. When your finished, the old window will lift out if it doesn't fall out, so don't hold on to the window when your cutting. Also wear a mask because this is very dusty. At this point, you should end up with a clean cut in the stucco. You should measure your window to be app that size, and you can do that before cutting. Give yourself a minimum of an extra 1/4 inch all the way around for easy fitment between the stucco. You will most likely be behind the sheetrock at that point, but that's not for sure. Once you do one, you'll know how to do the others better. Worse case, you'll have to cut the stucco twice on the first one. DO NOT forget to flash/drip cap above the new window. You can get up in there with a sawzall blade and cut the nails to remove the upper fin, which should give you plenty of clearance for your drip cap. Go ahead and rip out your sheetrock before installing the new window, and then just jamb up to it once it's determined where it will sit. You won't loose much glass area, if any, if you do it this way. The new window, in this situation, will stick out past the stucco app 3/8 of an inch. You will be able, hopefully, to put a nice neat bead of caulk around it that way, with no raw stucco edge showing. Be sure that you measure for this from the inside surface of the wall around the window all the way around, because stucco can be much much more uneven than the inside sheetrock. Don't forget you can measure where the studs are by measuring between the sheetrock on the inside and adding for the thickness of the sheetrock. Compare this measurement with what you get measuring the exposed aluminum frame on the outside - BUT, use your inside stud to stud measurements for your basis of determining the new window size. Also, do not forget, window sizes are always width first. width x height. Always. If this sounds like too much for you, bit the bullet and have the pros do it. If you don't know what you're doing it's not hard to butcher this kind of job. Worse worse case, you're patching stucco, but that will always have a tendency to crack where you patched it. And please be careful with power tools on ladders. Always have a helper or two. Preferably one to steady the ladder, and one to hold the window. Tie off the ladder, tie off yourself. I hope this makes sense to you. Good luck.

We're replacing windows in our 30 year old stucco house and are leaning toward Milgard vinyl Style Line series because of the narrower profile compared to the Tuscany series. Major question is longevity of caulking and maintenance needs of retrofit windows vs. new construction windows. Price is, of course, cheaper in the retrofit, and we're still debating whether the frames are good enough for it. Any advice on long term cost/benefit issues of new construction vs retrofit? Any thoughts on how much of an issue the mainenance of retrofit windows can become?

If that's dry rot I see at the bottom of your frame, its got to go, one way or another. A skilled carpenter (not a "door installer") could cut out the bad bottom section of the stud and replace it with minimal damage to the stucco, but that may be a moot issue. I'm replacing a slider in a stucco wall too and have found that you have to be very lucky to find door with a rough opening size that will just slip into to the old frame without a wide band of trim around the door. That will really be a negative for appearance so we're adding $400 to our budget to cover stucco repair. Most major window mfrs make patio doors in replacement sizes (Integrity does not) and the use of the nailing fin is preferred but optional. If not used, it's bent back out of the way or cut off.

Hi Shannon, To get the desired look, for the look you are trying to achieve, I would recommend the following based on our twelve years as a Windsor distributor/installer: 1) Windsor Legend double-hung windows with exterior moulding factory applied. This will give you the set-back look you are desiring and still allows the Hardie planks to "dive in" to the side of the window trim. We completed numerous homes, that were a farmhouse architectural typology, in the South Carolina Low Country as well as Savannah, GA area with the Windsor Legend series . 2) Windsor Next Dimension classic series with nail fin and no brickmould attached. You will still need to have the window recessed so it is set back, then have PVC exterior trim applied so the Hardie plank "dives in" to the window trim. If you are using 2 x 4 exterior walls, the builder will have to fur-out the inside of the window wall so the drywall and interior window trim can be applied appropriately. Hope this helps! Patrick