Why is s/he suggesting this? Think about that.

Is he proposing synthetic stucco over foam insulation board or real cementitious stucco on wire lath?

He's proposing adding wire lath on top of current siding and then putting stucco on top of that.

From what I can see of the house it seems like a Ranch rather than a Craftsman house. If that is the case, I suspect stucco might look inappropriate but I would need to see more of the house and neighboring houses to be sure.

Would the stucco be flush with the window and door trim?

Synthetic EIFS would add insulation to the wall and conserve energy. The amount depends on the climate. Cement stucco might add a slight mass effect to the wall but probably would not conserve much energy.

What does the contractor say the advantage of cement stucco would be? You may be trading one maintenance issue for another. I would update some of the detailing of the house. Is the siding lapped "drop" or "novelty" siding?

If you do it be sure to use a double layer of weather barrier or a drain mat and weather barrier with seeps at the bottom edges. If water cannot drain from behind the stucco you will have a serious problem.

I don't know where you're located but what gets stuccoed is somewhat regional. Where I am in CA, 50s ranches usually have stucco. And wood siding. And bricks and stone. And often all of the above, but this looks pre-50s. From what I can see, your house is maybe from the 40s? Sort of ranchy, sort of craftsman influenced cottagey? Is there a name for that? Is this California?

Your current siding looks very good and from what you've shown, stucco wouldn't look as nice. And if you're in CA (as opposed to other orange growing areas) the maintenance on the wood isn't terrible and shouldn't be a factor.

Adding stucco on top of the siding (not removing the wood?) would mess up your windows and door trim. They'd have to be redone. Are you sure that's what your contractor is proposing? It seems sort of wrong to do it that way, although maybe it's fine.

Is your contractor also pushing for the "color coat" stucco? The stuff that gets sprayed on, paint included? That'll supposedly never need painting ever again? The guys around here really love that stuff and push it pretty hard. It must be easy to do because they want to stucco everything. Using that is the only reason I can see for trying to get you to stucco that siding.

You are all, it's ranch and not craftsman. I got confused. You are right on. It's 1940s CA ranch style. I am just wondering if doing it would add value to house and less maintenance and better for long term. And whether it's better for winters and hot summers.

Contractor said he would replace all windows to make it flush.

There shouldn't be a significant difference in maintenance. (My house has both.) The siding you have now is probably a little more work to repaint than stucco would be, but it's not something you do very often. The siding IS easier to repair should a repair be necessary.

I don't think stucco would look as good as what you have now, though.

For energy savings, you might look into having insulation blown into the walls. That would be a much better fix.

So anyway, I wouldn't do it. Stuccoing over all that, aside from being weird, would greatly reduce the charm of the place. If you do go ahead and stucco all over, please don't do that ghastly stucco window "trim" that is so often done when people try to de-ranchify their ranches. It only looks right on Walmarts.

And I would like to see a pro's opinion on stuccoing OVER siding. I've never heard of such a thing!

I'm in Cali and have both stucco and wood siding. The paint on the stucco has held up very, very well compared to the paint on the wood siding. While the exposed wood areas are in dire need of paint, the stucco looks perfectly fine. That could possibly have something to do with inadequate prep before painting, though, as I don't think my painter was very thorough. We've considered getting rid of the wood and putting stucco on the entire house, but if we did do that, we'd remove the wood siding rather than stuccoing over it. But my wood siding doesn't look nearly as nice as yours, and if it did, I wouldn't even think about changing it. Your house looks really charming just like it is. Stucco the whole thing and it will look like one of a gazillion tract homes.

How will they detail the stucco terminating under the rake boards, which are applied over the siding (no gable overhang)? That is an invitation to letting water in behind the stucco, and the consequences are dire. I'm sure there is a flashing-based solution, but then the rake boards will be flush (the shadow line you have now will disappear). The solution to that is only one thing: re-roof, and add back in the shadow line, making the roof an inch deeper on all of the gables/rakes. This is the point where it gets more expen$ive.
Casey

Having grown up in S CA, I can say that siding is a pleasing thing. CA does not need another stucco house.
Diane

Scott-
I'm glad you decided against this as it looked to me like it would create problems when you don't appear to have any to start with. The reason I am posting is to suggest you think about this contractor and why he is proposing to do expensive, non-essential work. If that were my house and I was getting that kind of advice from a contractor, I would be very careful employing that person. Good luck.