The Ultimate Exterior Home Maintenance Checklist For 2025
Oconomowoc home exterior remodeling project in progress

Even if it feels like your home is in tip-top shape, there might be hidden cracks lurking beneath the surface… Or maybe right on your roof. Either way, no one wants to deal with outrageously expensive exterior home maintenance. After all, doing the dishes and cleaning up the kids’ mess is a back breaker as it is–let alone taking care of siding, gutters, and everything else outside the front door.

So instead of letting Wisconsin’s four-season climate beat up your house without your permission, we’re here to give you the ultimate exterior home maintenance checklist for 2025. We’ll cover how to find damage on your roof, siding, windows, and more!  

With this guide, you’ll be able to inspect your house like the pros, and find any issues before they snowball into a hefty repair. Grab your glasses and a notebook, and let’s inspect your home!

Looking For Something In Particular?

Roof Inspection

Out in the Midwest where heavy snow, ice, and hail are bound to hit your home, you’ll want a sturdy roof to keep you covered. And unless you’re stargazing on your shingles every other week, you probably won’t notice any damage on your roof until it’s too late. So here’s how to inspect your roof.

Signs Your Roof Needs A Repair Or Replacement

  • Curling or buckling shingles – when the edges curl or look cupped
  • Missing or cracked shingles – exposes your roof to leaks
  • Bald spots – when your shingles lose the asphalt (granules)
  • Brown water stains (or indoor leaks)
  • Sagging roof – When your roof looks uneven or slightly sinks due to rotting wood or weak spots
  • Moss or algae growth – collects moisture and can shorten your roof’s lifespan

How Often Should You Inspect Your Roof?

Since the Midwest slews summer storms and harsh winters, you’ll want to inspect your roof twice a year–in both the spring and fall. It’s better to catch issues early before they evolve into major damage (and a financial headache). If you’re unsure a potential bruise may lead to something bigger, you can always ask a contractor for an expert inspection. 

exterior home maintenance: roof repairs

How to Inspect Your Roof Safely

If you’ve never checked out your roof before, don’t worry, you won’t need to climb on a slippery roof to get the job done. You can use binoculars to scope it out from the ground, and look for the signs we mentioned earlier. If you want a thorough inspection by yourself, feel free to use a ladder–make sure someone stabilizes it–to check those blind spots. Don’t climb on your roof if it’s icy or steep. 

Pro Tip: On a sunny day, head up to your attic and see if you notice any light coming through the roof. Those are your hidden cracks!

Siding Maintenance

The sides of your home not only protect it from mother nature, but also gives your home its neighborhood reputation! While the roof is like the head of your home, the siding is the skin–let’s check for any bruises.

Signs of Siding Damage

  • Cracks or gaps – even the smallest cracks let air and moisture in. You’ll want to replace cracks as soon as you can to prevent any water from coming in.
  • Warping or bulging – warped (or wavy) siding, like shingles, are a sign of water damage or heat warping. 
  • Rot/soft spots – Soft, spongy wood or visible rot means the material has been altered by moisture and likely needs replacing.
  • Mold, Mildew, or Fungus – this should be easy to spot. Look for green/black spots, especially towards the bottom of your home. You can prevent this by making sure your sprinkles aren’t drowning your siding
  • Blistering, bubbling, or peeling paint – If you spot any bubbles, those might be pockets of moisture that shouldn’t be getting into your walls. If they come back even after repainting, it’s a sign you might need to replace your siding

When Should You Repair or Replace Your Siding?

Deciding whether to repair or replace your siding comes down to the severity of the damage

  • If the damage is focused on a specific area (ex: cracked panels from a baseball), you can usually repair and patch it–you can even do it on your own if you’d like. You’d want to replace the panels and paint it to match the rest of the home.
  • If the damage is widespread (ex: warping on an entire side of the house), it makes more sense to replace the siding on the wall or even the whole house. If you were to patch each spot, that might actually cost you more and potentially even miss the root issues that caused the warping.
exterior home maintenance: siding damage

Also consider your siding’s age and maintenance, you shouldn’t need to be constantly touching up your siding.

Popular Siding Options for Curb Appeal

Let’s say you need siding replacement, what type should you choose? 

Vinyl siding is a popular choice in the Midwest as it’s affordable and you won’t need to patch it up every month. Opt for fiber cement if you want something durable and aesthetic, engineered wood for a natural wood look, or metal for durable accents. You might even consider brick or stone veneer, for a more luxurious and rustic look (and the big bad wolf won’t blow it away).

Check Your Windows, They Might Have This…

On top of giving your home views of Waukesha, windows also keep your home warm and even affect your energy bills. If you’ve been feeling winter drafts while binge-watching Netflix, your windows might be to blame (not your AC unit). So here’s how to investigate your panes.

Signs Your Windows Might Be Failing

  • Drafts – if you feel air coming in around the frame, your window’s insulation isn’t doing its job.
  • Condensation or fog between panes – that’s a broken seal. Time to get it looked at.
  • Hard to open or close – windows should slide smooth, not feel like a workout.
  • Rising energy bills – if the numbers look funny on your bill, the poor insulation is making your HVAC work overtime.
  • Cracks – duh!

When To Repair vs. Replace

If it’s just a little draft or one broken latch, you can probably fix it up with weatherstripping, caulk, or new hardware. But if you have foggy glass in multiple windows or wood rot around the frames, it’s probably time for a replacement. Especially if they’re decades old.

Energy-Efficient Window Upgrades That Pay Off

When you do upgrade, look for double-pane windows with Low-E coatings and argon gas fills. These features trap heat inside in the winter and reflect heat out in the summer—saving you money every month. 

Bonus: They dull down the noise from the kids playing outside, too. 

Clean Your Gutters!

Your gutters may be boring, and quite possible the most overlooked part of your home, but they do one of the most important jobs in your house—keeping water away from your foundation. If they’re clogged, sagging, or leaking, you could be in for a world of trouble.

Why Clogged Gutters Are A Nightmare

Water that doesn’t drain properly can pool around the base of your home, leading to cracks, leaks, and a flooded basement. In the winter, clogged gutters cause ice dams that push water under your shingles. Yikes. Doesn’t seem like something you want to skip now, eh?

How To Gut Your Gutter Problems

  1. Clean them out twice a year (spring and fall)
  2. Install gutter guards if you’re surrounded by trees
  3. Make sure downspouts carry water at least 5 feet away from your home to avoid pools and puddles
  4. Patch small leaks with gutter sealant

When To Call A Pro

If your gutters are sagging, pulling away from the house, or your second-story is out of reach, it’s safer (and smarter) to call a contractor. They’ll re-secure, rehang, or replace what’s needed to keep things flowing smoothly.

Open Door Policy, Anyone?

Knock knock, who’s there? Hopefully not any issues with your door… Whether it’s a security concern or just plain ugly, here’s how to check if it needs an upgrade.

When It’s Time for a New Door

If it’s hard to open or close, you feel a draft, or see daylight around the edges it’s probably time for a new door. Also make sure, like your siding and roof, the door isn’t warped, rotting, or rusting. This should be pretty easy to spot. While you’re at it, double check the lock for security.

How to Improve Security and Efficiency

Add weatherstripping to stop air leaks, and reinforce deadbolts with longer screws and a strike plate. If your door feels flimsy or outdated, upgrading to a steel or fiberglass option boosts both safety and energy performance.

Don’t Forget Curb Appeal

A fresh front door can completely change your home’s vibe. Whether you choose classic woodgrain or a bold color, your front entrance sets the tone for the rest of the house. Always keep your creative mind running, even when it comes to exterior projects!

Storm Damage

Midwest storms don’t mess around. Hail, heavy wind, and flying debris can do serious damage in a flash. While you can’t control the weather… Here’s what to do if your home takes a hit:

What To Do Immediately After A Major Storm

  1. Check everyone is safe first
  2. Walk the property (safely) and document damage with photos
  3. Look for missing shingles, cracked siding, broken windows, or flooded areas
  4. Temporarily cover broken areas with tarps or boards

Insurance Tips

  • File a claim ASAP—don’t wait too long or you run the risk of missing the time requirement
  • Keep records of everything (with photos or receipts)
  • Ask about your coverage: do you have a replacement cost or actual cash value?
  • If needed, get quotes from contractors to compare with your adjuster’s estimate

Choosing A Contractor

Storm chasers might show up out of nowhere—be careful. Stick with a trusted local company that’s licensed and insured. Ask about warranties, and never pay 100% up front.

A Home Protected From The Weather

Great! Now you have pristine windows that protect your home and your energy bill, a moss-free, storm-ridden roof, with gutters that flow freely, and your front door is more than a first impression. You’ve taken the time to safeguard your home before the upcoming storm, well done.

But if that isn’t the case and you need a helping hand getting there… We’ve got your back. From roof inspection to siding replacement and everything in between, our team of experts is here to get our hands dirty and patch up your house.

You handle the inside—we’ll protect the outside. Get your exterior dialed in by the pros. Includes a FREE quote.

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