What does gutter cleaning involve on a big house with a cedar shake roof? On Monday, November 2, 2026, it took our technician Davey 1 hour and 25 minutes, and the invoice came to $325.
This job happened earlier this week, and we’re writing it up from our job log, the photos Davey took from the ladder, and the invoice. The house is brick, about 4,000 sq ft, built in 1986. We picked it because of the roof. Weathered wood shakes need more care than asphalt shingles at the exact spot where a gutter cleaner works, and the gutters on a roof like this protect more than the siding.
If you’re thinking about professional gutter cleaning for a home like this one, here’s what the visit looked like.
We’ve left out the homeowner’s name, address and town. The times, photos and price are from the real job.
The Numbers From This Job
| Detail | This job |
|---|---|
| House | Brick, about 4,000 sq ft |
| Built | 1986 |
| Roof | Cedar shake |
| Gutters | Open gutters, no guards |
| Date | Monday, November 2, 2026 |
| Technician | Davey |
| Drive to the job | 46 minutes |
| Time on the job | 1 hour 25 minutes |
| Price | $325 |
What Was Actually in the Gutters?
Davey marked the job “on my way” at 7:25 AM and started at 8:11, early in the 8:00 to 10:00 AM arrival window.
The gutters weren’t packed end to end. The photo at the top of this page shows the pattern: clumps of curled oak leaves, with bare stretches of dark sediment in between.
Look at where the clumps sit. Most are up against the hangers, the metal straps that hold the gutter to the roof edge. A hanger catches the first few leaves, those leaves catch the next ones, and a clump grows from there. A gutter can look half empty and still have a small dam every few feet.
Oak leaves make that worse. They’re tough, they break down slowly, and they mat together, so a clump holds water instead of letting it through. Moss was growing along the back wall of the gutter beside one downspout outlet, and moss needs damp conditions to get established.
Dry oak leaves piled against a hanger, and moss along the back wall of the gutter next to a downspout outlet.
Why Does a Cedar Shake Roof Change Gutter Cleaning?
There are two reasons: the ladder and the water.
The ladder. An extension ladder has to rest on something at the top. Leaned against a gutter, it can dent or bend it. Set down carelessly on old shakes, it can crack them. So Davey used a standoff, a curved aluminum arm with a padded end, which you can see in the photo further down. The pad sits on the shakes and the arm holds the ladder clear of the gutter. A bucket hung from the ladder takes the leaves.
The angle matters as much as the padding. NIOSH, the federal workplace safety research agency, puts the proper ladder angle at about 75 degrees, and its free Ladder Safety app will measure it for you if you ever set up your own ladder.
All of the photos in this post were taken from the ladder, which is where a wood roof wants you. The Cedar Shake & Shingle Bureau’s maintenance FAQ doesn’t advise homeowners to walk on their roofs, and it recommends a trained contractor with safety equipment for any roof survey.
The water. A wood roof needs to dry out between rains. Oregon State University Extension’s guide to caring for wood shingle and shake roofs explains that neglected gutters can back water up as far as the lowest row of the roof. It also notes that moss and lichen hold debris, which keeps the wood wet for longer and encourages decay.
So on a shake roof, a blocked gutter isn’t only a risk to your siding and foundation. It can keep the bottom of the roof itself wet.
You can also see dark growth along the lower edges of the shakes in these photos. This visit was for the gutters, and the roof itself wasn’t treated. If your roof looks similar, get advice before anyone points a pressure washer at it. The same Oregon State guide warns that careless power washing can damage the wood and fracture shingles.
Where Did the 85 Minutes Go?
Mostly into the size of the house. In August we cleaned a one-story home in Oakwood Hills, about 1,400 sq ft, in 33 minutes. This house is nearly three times the size and took about two and a half times as long.
| Detail | This job | Oakwood |
|---|---|---|
| House size | 4,000 sq ft | 1,400 sq ft |
| Month | November | August |
| In the gutters | Oak leaves | Maple leaves |
| Drive | 46 min | 42 min |
| On the job | 85 min | 33 min |
| Invoice total | $325 | $135 |
More house means more gutter, more corners and more ladder moves. Each time a run ends, the ladder comes down, moves along and gets set up again, with the pad placed back on the shakes. Davey’s photos were taken from at least three spots around this house.
The work itself doesn’t change with the size of the house. Every visit is the same job: every gutter cleared, every downspout flushed, debris bagged and hauled away, and photos sent when we finish. Here’s the full checklist of what’s included in gutter cleaning.
After: a long run with the leaves gone, and an open downspout outlet with the padded standoff resting on the shakes.
Look closely at those two photos. The gutter isn’t spotless. The leaves are gone and the outlet is open, but the metal is still stained, which is normal on a gutter that has been up for years. What matters is that water has a clear path from the roof edge to the ground.
What Did the Invoice Say?
| Line item | Amount |
|---|---|
| Gutter cleaning | $325.00 |
| Total | $325.00 |
The invoice went to the homeowner after the job, and it has been paid. Prices depend on the house, and our gutter cleaning cost guide walks through what moves a price, with worked examples.
Is One Cleaning Enough on a Lot Like This?
Probably not, and the photos show why. On November 2 the gutters already held oak leaves, while the trees around the house still had plenty of brown and orange leaves left to drop.
Oaks are the slowest trees to finish. Many hold their dead leaves well into winter and let them go a few at a time, which is why it pays to time your fall gutter cleaning around your trees rather than the calendar. For a home like this, we’d suggest:
- An early November cleaning (done) to get the gutters draining before freezing weather.
- A second look once the trees are mostly bare, because the leaves still on those branches have to land somewhere.
- A spring check, because oaks can hold some leaves until the new buds push them off, and then they shed their tassels.
The window is short. The National Weather Service’s snow climatology for the Chicago area puts the normal first measurable snowfall at November 18, just 16 days after this job. Wet oak leaves left in a gutter can freeze in place, and that’s how many ice dams start. On a wood roof, the bottom row is the last place you want meltwater sitting.
Would guards change this? With whole leaves, yes. They don’t end the maintenance, though. Fine grit and oak tassels still settle on the mesh, and guarded gutters take more work to clean. Our gutter guards page covers the options.
Questions We Get About Jobs Like This
Yes, with the right setup. On this job our technician used a ladder standoff with a padded end, so the pad rested on the shakes and the ladder stayed clear of the gutter, and the gutters were cleared from the ladder. Weathered shakes can crack under a hard point of pressure, which is why the setup matters so much on a wood roof.
This one took 1 hour and 25 minutes on the job, plus a 46-minute drive. A bigger house means more gutter, more corners and more ladder moves, and the number of stories, the access around the house and the amount of debris can all change the time.
$325, shown as one gutter cleaning line on the invoice. The invoice went to the homeowner after the job and has been paid. Prices depend on the house, so call or ask for a free estimate to get a number for yours.
No, because you want the gutters draining before freezing weather arrives. It may not be the last cleaning of the year, though. The trees around this house were still holding leaves on November 2, and many oaks keep shedding well into winter, so a second look once they are mostly bare is worth it.
The takeaway: a cedar shake roof doesn’t rule out a normal gutter cleaning. It makes the ladder setup matter more, and it gives you one more reason to keep the gutters draining. This one took 1 hour and 25 minutes and cost $325, and the oaks will decide whether it needs another visit this year.
Have a cedar shake roof, or oaks hanging over your gutters? Call (224) 386-4836 or ask for a free gutter cleaning estimate. Tell us your town, how many stories you have, what your roof is made of and what’s growing over it, and we’ll give you a price and an honest schedule.
