I would contact via a PM RES from this forum RES2 - Newton, MA, US 02461 | Houzz He'll know all about windows in your area as he lives there. And he's a talented architect if you don't already have one.

Yes get a Pro's guidance. I do live south of Boston and don't find many stucco houses. I have a Cape Cod style house built in the late 60's: cedar shingles & wood trim. We did replace the shingles because they were not properly cared for by previous owners but 90% of the wood trim is original. Hardie board is now very popular here. We put in Pella aluminum clad wood interior windows 20 years ago they are ok but I wouldn't get them again.

Older stucco homes I've seen in the area inevitably have poorly repaired large cracks in the material. It's an uncommon siding in the region which implies that skilled tradesmen are not plentiful. I'd go with a fiber cement siding. Winters are harsh and exterior clad windows are a good choice. Get the best windows you can - construction, materials, operation, parts availability. There are various levels of quality from each manufacturer. I have 1978 Andersons and they are solid though some casement operators are failing and some of the glass is fogging. A relative put in a mid-grade Anderson in 2020 and the frame was failing within the year.

I'm now retired so you need to ask me questions while my memory is still intact.

18" cedar shingle perfections provide triple coverage and will last as long as you are likely to live in the house but they do require some maintenance if you want them to look like they did when installed. Most New Englanders don't care about that but, if you do, you should use an imitative material of which I only know what I have read. If synthetic cladding were avaialble without an embossed pattern I might have used it.

The best person to talk to about windows is Joe Adams at JB Sash & Door in Chelsea, MA 617 884 8940. https://jbsash.com/commercial-windows-and-doors/

They sell Marvin and have recently dropped Andersen which, similar to Pella, hasn't kept up their customer service and technical improvements. I recommend Marvin's "Elevate" series fiberglass clad wood windows or their "Ultimate" series if your budget will allow it. I believe its possibile to order these windows with a different color sash and frame which can be a bit more elegant than all one color. I've not used fixed winows or casements except for a few basement emergency escape openings and windows in showers.

Trim should be cellular PVC or a composite.

Most windows need a sub sill to allow water to drip over the exterior cladding (Azek Historic Sill AZM 6930 or equal).

Roofs need 5/8 or 3/4 sheathing and fullcoverage Ice & Water Shield underlayment.

I recommend a sealed attic with spray foam against the roof sheathing and provision for future expansion into that space if appropriate. New Englanders are frugal with space and like attics and basements..

Foam the ceiling of a garage if the space above it will be habitable.

At roof eaves trusses should have a "raised heel" and attic rafters should rest on a double plate on an attic floor; this raises the roof about a foot allowing for better insulation placement in the eaves and more exterior wall above the windows.

Good luck.

I would not do stucco but really witoutseeing the house at least drawings who knows what finishes are right for the house I lkke black metal windows no matter where the house is and there are many to choose from so look at what is available near you so you can check them out in person. I do not love casement windows many times so agin I need to see the house. I had aluminum clad wood in Calagry for years no issues but check what is appropriate in Boston and trust your architect to help with these decisions .

Can Hardie board deliver a more contemporary look?

Would the stucco be cementitious or Exterior Insulation Finish System (EIFS)?

@RES2, I sent you a DM but we’re still awaiting clarity on that!

Whatever finish you did (traditional stucco or EIFs) would incorporate a 1x4 PVC trim around the windows for serviceability down the road so that you don't need to rip out the exterior cladding/finish.

Thanks for the input - do you still need the PVC trim if you use a different type of exterior finish or is that only true for stucco?