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Your best bet is to contact some contractors and get estimates. There's no way to give you a ball park figure. I don't know how big your house is, if there are any updates, where your electric and water are located, permits, structural issues, etc. Also, be aware of the towns property barriers and the building limit. You have to have so many feet between your structure and your property line.
Just a basic 2 car garage - not 30x40 - is at least $20K with concrete and excavating. The building you want above the garage will require permits from the town. If you want it to be a separate living space, you may run into issues if you are not zoned for multi family.
It's a shed dormer and it doesn't square off the roof.
Ask around for contractors names and get estimates. That's the only way you can get an actual idea of costs. It sounds like a huge project and there could be permit issues. Permits are fun......sigh
Also, if you plan on a fence, deck, or patio or anything like this, you'll need permits for them as well. We're permit happy up here!
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