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Cement Board siding by someone like Hardi-plank can look like shingles and is not environmentally toxic. You cold also do panels of it for a more modern look. Down with vinyl siding.

Congrat's on your new house. It's adorable.
But what's wrong with the weatherboards currently on it?
Could you live with what you've got--at least until you save enough for the cedar shingles of your heart's desire?

HardieShingle® Siding - and the color is an intrinsic part of the siding so that painting isn't an issue.

http://www.jameshardie.com/homeowner/products_siding_hardieshingleSiding.py

And as far as windows, remember that you don't need to replace the entire casing, etc - Replacement sash units can be retrofitted into your existing casings if they're still in good condition.

http://www.andersenwindows.com/servlet/Satellite/AW/Page/awGeneral-3/1162992733936

How about fiber cement? It's lightweight, fire-retardant and insulating. They can make it look like cedar shingles. It might be the same thing as cement board that the first commenter mentioned.

Hardi-board of any type: shingles, panels, planks, even soffit pieces turned horizontally. You can be creative but the success depends on the contractor. The stuff is also high in recycled content. Before you put on new siding, check the waterproof sheathing underneath your siding. After 50 years, it could need a re-wrap. As for the roof, best low cost option is 20 year, energy star shingles. Don't let them do it without increasing the R-value of the roofing insulation. Dreams of standing seam metal dance in my head!

Please don't go vinyl ... it's so vile.

But Hardi-plank is outrageously expensive.

I say just sit tight for now. Cute house.

would stucco work or facing with stone?

Do you really have to put up siding? The house looks like it's in good condition. Are there termites or something we can't see? No weatherproofing?

Not sure why you're doing this -- aesthetics or necessity?

I just bought a new home and have had to ask some of the same questions as you, so here goes (this post is long...)

First, the house is really cute, there's definitely some hidden potential there. I agree with a some of the posters above, if you're looking to change the siding merely for aesthetics, wait and save up the money for those cedar shingles you're dreaming of (the're tougher than you think)! It looks like you might have aluminium siding... which is pretty tough stuff and fairly long lasing (I know it looks bad when dented and it's hard to replace damaged sections).

If you absolutely have to change the siding now and vinyl is all you can afford, keep an eye out for vinyl siding with some built in insulation (usually styrofoam) it tends to have an r-value somewhere between 3-5. At least you can offset some of the toxic plastic with siding that reduces your heating/cooling bill.

As for color have fun it's your house, just make sure you have some kind of vision for the overall look of the house. Try to pick the roof, trim, siding, door color, shutters, (even the landscape materials) before buying anything. It will save you headaches down the road. And remember that darker vinyl siding almost always fades and warps, especially the cheaper stuff (even if the warranty says it won't...).

As for the roof, cur1ous1 mentioned 20year energy star shingles, which is your best option on a low budget; just so you know midwest winters can easily chop a few years of the expected lifespan of asphalt shingles, even when installed to perfection (once again check the warranty). If you can wait, energystar rated metal shingles are available on the market with 50 year warranties (and metal roofs can easily last longer then that), and while they are more expensive to install up front, in the long run they usually come out to be cheaper (plus you save on the landfill waste the roof would have generated being shingled three times with typical shingles). And the warranty is transferable in a lot of cases, which can be a good selling point. (I don't work for a shingling company, just so you know).

Hope this helps!

Have you considered wood?

I had my garage done with barnboard planks last year and like the look so much I am planning on removing the evil vinyl the back of my house is clad in - the remainder is Victorian brick, thankfully - and use barnboard to replace it.

Barnboard is cheap and weathers beautifully to a silvery gray. It has a life expectancy of 30 to 50 years up here in Ontario and is easily replaced. My planks are 3/4 of an inch thick.

dont fix what doesnt need fixing..save up your money for other house projects (which WILL come up!).
replace any rotten or messed up portions, but for the most part, that looks in good condition.
spruce it up with some work on those shutters...a new color for those & the trim will be nice

Paint it unless there is some practical need to replace it. Save till you can afford what you really want. Don't do vinyl. Don't do vinyl. Just don't. A great paint job hides a lot of sins. It could transform it into something you like till you can make changes. No vinyl.

I am perplexed by the lecture-and-link about the evils of vinyl followed by the shrug of "Eh, it's all I can afford."

If you feel so strongly about the material, then hold off until you have researched a viable alternative.

Having lived in my little 'fixer upper' (AKA slated for demolition) cottage for almost a decade, I can't stress too strongly the need for patience (unless your aim is to improve and resell quickly). I totally agree with those who say to fix what has to be fixed and save your money for what you want most. As you live in the house, what you 'want most' may change a bit--and you'll certainly discover more things that need fixing.

And, as others have said, paint is a WONDERFUL thing. Cheap as chips and DIY friendly when you've only got a little bit of house to work on. Have fun with it!

I would leave the siding and just paint it.

"Cement Board siding by someone like Hardi-plank can look like shingles and is not environmentally toxic."

Since when is cement not environmentally toxic? Cement production is about as Earth-friendly as a patio heater.

For once I agree with patrick (the other one).

If you are concerned about the environment, the most environmentally friendly option is don't fix it if it ain't broke.

You can get wood siding and wood windows from a building goods recycling store (like Re-Store), thus saving the material from a landfill, not using vinyl, not creating a new product, AND saving money. (and wood looks better than vinyl, be it window or door).

Though fiber cement does have its environmental downsides, it is very durable and will last an incredibly long time. Balancing embodied energy or toxicity vs. lifespan makes a big difference. Vinyl on the other hand may last you 20 years _if_ you're lucky. While the shingle style of hardi planks are pretty expensive, the clapboard style are not, they aren't significantly different from medium to high end vinyl. There are also mid- grade white cedar shingles that aren't outrageously expensive. Being from the east coast and not the midwest, I'm not sure what aspect of the midwestern climate isn't good for cedar- hasn't it been used there for over a hundred years?

If you're really looking for the most environmental bang for your buck, leave the siding alone, maybe just patch and paint for now, repair any leaks in the windows- save money for better ones later and caulk and add insulation. If the house is minimally or not insulated, a few rolls of batting in the attic will make a much bigger difference than new windows.

Not only does cement siding last a long time, it holds paint well AND your insurance company might give you a break because cement is fire resistant.

@andreasduess: Can you post a link to a picture? Would love to see how your barnboard garage turned out. I'm in Ontario too. We used it for our fencing and love the result. But our house has siding on the sides and the back that could use a facelift, so we're considering our options. Barnboard could work really well, I think. Did you do the installation yourself?