Winter in southern Maine is hard on roofs, and when you manage several buildings the problems tend to arrive together. The first big storm, a freeze-thaw week in January and a March rain on top of snow can turn small defects into leaks across a whole portfolio in a few days. A walk around each roof in the fall is the cheapest way to get ahead of that.
Here is what to check before the snow, building by building.
1. Gutters, downspouts and roof drains
Meltwater needs somewhere to go. When gutters are packed with leaves or a flat-roof drain is half blocked, water backs up, freezes and starts working under shingles or membrane seams. Clear every gutter after the leaves are down, flush the downspouts, and make sure flat-roof drains and scuppers have their strainers in place and nothing piled around them.
Look at where the downspouts discharge too. Water dumped against a foundation in December becomes ice on a walkway in January, which is a liability problem as much as a roofing one.
2. Flashing at walls, chimneys, vents and skylights
Most roof leaks are not in the middle of the roof. They start where the roof meets something: a chimney, a sidewall, a plumbing vent, a skylight or a rooftop unit. Check that metal flashing is tight, that sealant has not cracked or pulled away, and that rubber pipe boots are not split. These are quick repairs in the fall and slow ones once everything is frozen.
3. Missing, cracked or lifted shingles
Walk the roof or look from a ladder or lift for shingles that are missing, curled or lifted at the edges. A lifted shingle is easy for the next nor'easter to tear off, and it leaves the roof open right before snow sits on it for weeks. Note granule loss and bare spots as well. They tell you a roof is near the end of its life and belongs in next year's budget.
4. Flat-roof seams, edges and ponding
On EPDM rubber, TPO and other low-slope roofs, look closely at seams, perimeter edges and anywhere the membrane turns up a wall. Note any areas where water ponds for more than a couple of days after rain. Standing water is where ice forms and where membranes wear out first.
5. Ice dam history and attic conditions
If a building had ice dams last winter, it will probably have them again unless something changes. Ice dams form when heat escaping through the roof melts snow, and the water refreezes at the colder eaves. The long-term fix is usually better attic air sealing, insulation and ventilation. Before winter, at least note which buildings and which roof sections had trouble, so you can respond quickly. Our ice dam page explains removal and prevention.
6. Trees and overhanging branches
Snow and ice add a lot of weight to branches. Limbs hanging over a roof should be noted and trimmed where possible, since a falling branch in a storm can puncture a roof and pull down gutters.
7. Write it down for every building
The most useful thing to come out of a fall roof walk is a record. For each building, keep:
- The date of the inspection and who did it
- Photos of anything that needs attention
- What was fixed on the spot
- What needs repair before winter, and what can wait for spring
- A rough sense of how many years the roof has left
When to call a roofer
A roof walk is not something to do in icy conditions or on a steep roof without the right equipment. If you would rather have it handled, a roofing contractor can inspect every building, make small repairs while on the roof and give you a written report for each one.
Pine Tree Roofing & Exteriors does pre-winter roof walks for property managers and condo associations across Greater Portland, York County and Lewiston-Auburn. The inspection is free, and you get a written report and quote for each building. Call (207) 731-8136 or request a roof walk online.
Frequently Asked Questions
When should a property manager schedule a fall roof inspection in Maine?
After most leaves are down and before the first lasting snow, usually October into November. Inspections can continue into winter as long as the roof is safe to walk.
What causes most winter roof leaks on apartment and condo buildings?
Blocked gutters and drains, failed flashing where the roof meets walls, chimneys and vents, and ice dams at the eaves. All three are easier and cheaper to deal with before the snow.
Need Help With Your Roof or Siding?
Book a free inspection. We'll look over your house, explain what we find and tell you straight what it needs, if anything.

