Start with water, not snow
Most of the winter damage we get called about isn't caused by snow. It's caused by water that had nowhere to go. A clogged gutter, a downspout dumping against a foundation, a roof valley packed with pine needles — all of it holds water, that water freezes, and ice expands into whatever is closest. So the first pass through the property is about giving meltwater a clear path off the roof and away from the house.
Clear the gutters after the leaves are actually down. Do it in late September and you'll be doing it again in November. Then check that every downspout still discharges a few feet out from the foundation, and that the extensions haven't been knocked loose by a mower over the summer — that's the single most common thing we find, and it's the reason for a lot of wet basements in March.
Get on the roof once, on purpose
One deliberate look now beats finding out in February. What matters: granules collecting in the gutters, shingles curling or cupping at the edges, flashing where the roof meets a chimney or a wall, and the rubber boots around plumbing vents, which crack and go brittle somewhere around the ten to fifteen year mark.
A flashing repair in October costs a couple hundred dollars. The same leak found in February is a ceiling repair, an insulation replacement, and a roofer working around snow. Three signs your roof won't make it through another winter covers what to look for in more detail.
The attic is a winter problem
Heat escaping into the attic is what causes ice dams, and ice dams are what cause the leaks that show up on ceilings in January. Two things matter up there: whether the insulation is even rather than just present, and whether the soffit and ridge vents are actually clear.
What we usually find is insulation that's been shoved aside near the eaves by someone who was up there running a wire, blown-in insulation packed into the soffit vents so no air can move, or a bathroom fan venting straight into the attic instead of out through the roof. Any one of those turns a cold attic into a warm one. Here's the full explanation of how ice dams form and what actually stops them.
Shut down anything that holds water
Hose bibs drained, and the hoses disconnected. A garden hose left attached over winter is one of the most reliable ways to split a pipe inside a wall, because the hose holds water against the valve and it freezes from the outside in. Irrigation blown out. Outdoor showers drained. Docks and lifts out or secured.
For unheated outbuildings and crawlspaces, shut the water off at the valve and drain the line, rather than just turning off the fixture at the end of it.
Heat, before you need it
Furnace or boiler serviced and filters changed — but more importantly, if a place sits empty for any stretch, know how the heat would fail and how you'd find out. A furnace that quits in early January in an empty house isn't a furnace bill. It's a whole-house plumbing bill, plus drywall, plus flooring.
A smart thermostat with a low-temperature alert, or a standalone freeze alarm, runs well under a hundred dollars and is the cheapest insurance in this entire list. Worth it for any seasonal place, any rental, and any house where you travel in winter.
Think about access while you still can
Driveway markers go in before the ground freezes, not after. Decide now where snow is going to get piled, and make sure that isn't against a garage door, on top of a septic field, or blocking the propane fill or the gas meter. Anyone delivering propane in January needs a clear path, and so does anyone plowing.
If the property is a rental, walk the arrival the way a guest will: parking, the path to the door, and whether that path will still exist after eight inches of lake-effect snow and no one on site.
Vacant and seasonal places need a plan, not hope
Snow season here runs from roughly the first week of November into April, and a lot of properties around Emmet, Cheboygan and Charlevoix Counties sit empty through part of it. If nobody is coming, the water gets shut off and the lines drained. If somebody is coming, the heat stays at 55 and somebody checks on the place on a schedule — a real schedule, with dates, not an intention to swing by.
That's most of what we do for owners through the winter: scheduled checks, snow cleared before it becomes an ice sheet, and a phone call when something looks off rather than a surprise in the spring.