Around Portland, most house upkeep lands just before and during the rainy months. Clear gutters and downspouts in late fall, cover outdoor faucets before the first frost, test alarms and look for drips every month, and keep paint, stain and rot repair for July through September. Anything here you'd rather not climb a ladder for, we take on as handyman work.
This home maintenance checklist runs by month and starts in October, because that's when a west-side house begins taking on water. I'm Slava, and I have 7 years of hands-on repair work behind me. The order below is the order I'd follow on my own place .
Why does a Portland-area house need its own maintenance checklist?
Most lists you'll find online were written for somewhere else. They spend pages on ice dams, snow loads, hurricane shutters and air conditioners. A house on the west side of Portland lives through something simpler: a long wet half of the year and a short, dry summer.
The numbers from Portland International Airport show it plainly. NOAA's 1991-2020 normals put the year at 36.9 inches of rain, and 27.3 of those inches fall between October and March, about 74 percent. July and August together average roughly one inch. The airport sees around 32 nights a year at or below freezing, nearly all of them November through March, and only about 4 inches of snow. These are airport readings, not Beaverton or Cedar Mill ones, but they give the shape of the year.
Three things follow. Water handling is most of the job: gutters, downspouts, crawl spaces and the wood that rots when water sits on it. Freeze protection matters, but it's short and cheap. And any outside work that needs dry wood belongs in the narrow window when the wood is actually dry. The ice-dam and AC chapters on national lists rarely apply here.
What should you do each month?
Here's the year as a table, starting with the first wet month. Each row is short on purpose. The last column names the jobs people most often pass to someone else.

| Month | Outside | Inside | Hand it off? |
|---|---|---|---|
| October | First look at gutters as leaves start dropping; turn downspout outlets away from the foundation | Press the test button on every smoke and CO alarm; check the furnace filter (your job, not ours) | Gutter cleaning |
| November | Main gutter cleaning once the maples are bare; unhook hoses, shut off and cover outdoor faucets | Learn where the main water shut-off is; feel for drafts at exterior doors | Gutter cleaning, faucet covers, weatherstrip and door sweeps |
| December | Walk around during a hard rain and watch where the water goes: over the gutter lip, onto the siding, into a puddle by the wall | Look for condensation and soft paint on window sills | Downspout extensions and splash blocks |
| January | Shine a light into the crawl space from the hatch: standing water, sagging insulation, torn vent screens | Wrap any pipe that froze or came close | Pipe insulation, crawlspace vent screens |
| February | A second gutter pass if firs hang over the roof; start booking dry-season jobs | Push the test button on bathroom and kitchen GFCI outlets; redo cracked tub caulk | Tub and shower caulking |
| March | From the ground, look over the roof for moss and lifted shingles; check fence posts and gates after the winter | Pull the dryer lint screen and look at the duct behind the dryer | Roof moss removal by hand, dryer vent cleaning |
| April | Walk the deck and stairs: soft boards, loose railings | Run the bathroom fan during a shower and see if the mirror clears | Railing and step fixes |
| May | Wash siding and walkways if they're green (never the roof) | Check the water heater straps and clear stored things away from it | Pressure washing, water heater straps |
| June | Push a screwdriver into sills, fascia and the bottoms of door frames to find rot while there's time to fix it | Note anything that sticks, drips or leaks for the summer list | Rot repair |
| July-August | Paint, stain and seal decks, fences and trim; re-caulk windows | Nothing urgent; it's the outside's turn | Deck and fence staining, trim painting, window caulking |
| September | Refresh weatherstrip, door sweeps and window caulk before the rain; clear the last needles | Replace alarm batteries that have started chirping | Weatherproofing doors and windows |
The table fits on one printed page if you want it on the fridge .
What belongs on the monthly list, whatever the season?
A few checks don't care what month it is. They take ten minutes and catch the small leaks that become big ones.
Press the test button on each smoke and CO alarm. A battery alarm needs a fresh battery or a new unit once it gets old, so read the date printed on the back. Open the cabinets under each sink and look at the floor around the toilet base for dark spots or a soft feel. After any big windstorm, step outside and glance at the gutters and downspouts for anything bent, pulled loose or overflowing.
The furnace filter is a homeowner task too. Check it and swap it when it looks grey. Servicing the furnace or heat pump itself is work for a heating company, not a handyman.
What should you check from October to February, the wet and cold months?
Gutters come first. On a house under big trees they usually need a full cleaning after the leaves are down and a second look in late winter if firs stand over the roof. Our gutter cleaning page covers timing and price in detail . Where a downspout empties right next to the wall, an extension or a splash block carries the water a few feet out.
Outdoor faucets need attention before the first hard frost night. At the airport, November averages about four nights at or below freezing, and December and January about eight or nine each. Unhook every hose, close the inside shut-off valve if your house has one, open the outside tap to drain it, and put an insulated cover over the faucet. Some owners replace old faucets with frost-free ones instead .
Many 1960s-80s houses on the west side sit on crawl spaces, and that's where winter water shows up first. In January, open the access hatch and use a flashlight. Look for standing water, insulation hanging down from the floor above, and vent screens that are torn or missing. If the space looks wet or you're not sure it's safe to go in, don't .
Drafts are cheap to fix in winter. A worn door seal or a gap under the door lets in cold air and rain on the wind. We handle weatherstripping and door sweeps as a short visit. If a door starts sticking in damp weather, wait for summer before planing it, since the wood shrinks back once it dries out; our door-sticking guide explains why.
After a windstorm, look for branches lying on the roof or caught in the gutters. Storm damage repair is a separate job; tree removal and hauling are not things we do.
What should you check from March to June, as the rain eases?
Start with the roof, seen from the ground or from a ladder at the eave. Under Douglas firs, shingle roofs grow moss, and moss holds water against the shingles. Look for green mats, shingles with lifted edges and flashing that's pulled away. We take moss off by hand with brushes and scrapers . We don't spray chemicals on roofs or put up zinc strips.

Washing comes next. Siding, walkways and decks often go green over the winter, and they should be clean before you stain or paint anything. We wash siding, walks and decks, never a roof.
The deck, stairs and fence have just come through six wet months. Step on each deck board and stair tread, and lean on each railing. A fence post that rocks or a gate that drags has often started rotting at the ground line .
Two quick inside jobs fit here too. Pull the dryer out and look at the duct behind it: lint buildup or a flattened duct makes the dryer run long and hot. Then look at the water heater. Its earthquake straps should be snug, and nothing stored should be leaning against it.
What should you do in the dry months, July to September?
July and August average about one inch of rain combined at the airport. That's the window for any outside job that needs dry wood or time for paint and stain to cure. Because everyone wants the same weeks, booking in spring makes sense .

Fix rot first and paint second. Probe the window sills, fascia, trim and the bottom few inches of door frames. Paint over soft wood and it keeps rotting underneath, out of sight. Cut it out and replace it, then prime and paint. We do rot repair on sills and fascia through the dry months .
Then the coatings: stain or seal the deck and fence, and spot-paint trim and fascia where the paint has failed. Our guide on when to paint a house's exterior goes deeper on dates and temperatures.
One caution for older houses. If yours was built before 1978, old exterior paint may contain lead, and scraping or sanding it is a different kind of job. We don't disturb lead paint. Read our guide to Oregon's lead paint rules before anyone starts scraping.
September is for closing the house up. Re-caulk around windows and doors and replace weatherstrip that has gone flat, so it's done before October brings the rain back.
Which three items do west-side homeowners skip most?
- Downspouts that empty right at the foundation instead of a few feet out .
- Crawl-space vents and the access hatch, which some owners never open at all .
- Caulk and paint on south- and west-facing sills, where the sun cracks the finish and the rain gets in behind it .
Which jobs on the list are worth handing to a pro, and what do they cost?
Most items on this list are fine to do yourself. The ones people hand off usually involve a ladder, a crawl space or a few hours of steady work. Here's what the common ones cost around Portland.
| Job | Typical | Range | Basis |
|---|---|---|---|
| Gutter cleaning, gutters and downspouts | $285 | $175-$450 per job | labour only |
| Downspout extensions and splash blocks | $250 | $120-$500 per job | labour only |
| Gutter repair: leaks, sag, hangers | $350 | $150-$800 per job | labour only |
| Roof moss removal by hand | $425 | $225-$750 per roof | labour only |
| Hose bib shut-off and covers | $150 | $100-$250 per job | labour only |
| Pipe insulation, crawl space or garage | $400 | $200-$800 per job | labour only |
| Door weatherstrip replacement | $250 | $150-$400 per job | labour only |
| Door sweep and threshold | $250 | $150-$450 per job | labour only |
| Window caulking and sealing | $350 | $150-$800 per job | labour only |
| Tub and shower caulking | $250 | $150-$400 per job | labour only |
| Dryer vent cleaning | $143 | $103-$188 per job | labour only |
| Battery smoke and CO alarms installed | $200 | $120-$350 per job | labour only |
| Water heater earthquake straps | $250 | $150-$400 per job | labour only |
| Crawlspace vent screens and covers | $400 | $195-$850 per job | labour only |
| Pressure washing: siding, walks, driveway | $433 | $265-$601 per job | labour only |
| Deck staining and sealing | $850 | $550-$1,250 per deck | with materials |
Portland-area market ranges, November 2026 . Related jobs: a frost-free outdoor faucet runs $250-$650, rerouting a crushed dryer duct $250-$900, and door and window weatherproofing $200-$800, all labour only; fence staining is $500-$2,000 with materials, and trim and fascia spot-painting $400-$2,000, labour only .
The point of the cheap jobs is the expensive ones they can head off. Clearing a plugged gutter costs $175-$450 in this market. Rotted trim, fascia or sills behind it run $500-$4,000 with materials, soffit and fascia replacement $600-$6,000, and siding repair up to $6,500. Water getting into a crawl space costs $400-$3,000 to fix, labour only, and a small roof leak $350-$1,872 with materials. A clogged gutter doesn't always lead to any of that, but it's where a lot of it starts .
A common rule of thumb says to set aside about 1 percent of a home's value each year for upkeep. Treat it as a rough guide, not data. An older house under big trees tends to spend more of that budget on water and wood .
People often ask which repair costs the most. Roofs, foundations and water damage are the usual answers. Most of the costly ones begin as water going somewhere it shouldn't.
What does this checklist leave to other trades?
A handyman covers a lot of this list, not all of it. Furnace and heat-pump service belongs to a heating company. Garage doors and openers, chimney sweeping, lawn care and landscaping, tree removal, pest control, chemical moss treatment, gas lines and hauling all go to other specialists. Here's what we hand to other trades and why.
We don't sell maintenance plans or yearly contracts. Use the list, and when it turns up a job, text us about that job.
Most items here are repairs. If you're unsure whether something on your list needs a permit, our permit guide walks through it.
Does an older or newer west-side house change the list?
House age changes where you look first. Cedar Hills has many 1950s-60s tract houses, and Cedar Mill many from the 1960s and 70s. Those often still have original windows and doors, sit over crawl spaces, and may carry old paint under the newer coats (see the pre-1978 note in the dry-month section). Bolting an older house to its foundation is a separate seismic job, not a checklist item.
Bethany's houses mostly date from the 1990s and 2000s. At 25-30 years, the items that come due there are different: water heaters near the end of their life, first-generation decks and fences, and floors from the original build.
If you just bought a house, spend part of the first day finding three things: the main water shut-off, the electrical panel and the crawl-space hatch. If an inspection report came with the sale, start the list with what it flagged.
