A chimney or skylight leak in Winnipeg typically costs $250–$1,200 to repair, but the final price depends on the size of the job, the scope of the damage, and the site conditions of your roof, so treat that range as a starting point, not a firm quote. The most common causes are failed flashing, cracked boot seals, ice dam backup, and freeze-thaw cycles that open gaps around the penetration. Roof Repair Winnipeg finds the actual source, fixes it properly, and tells you honestly when a repair is smarter than a replacement, and when it isn't.
What a Chimney or Skylight Leak Actually Is
A chimney or skylight leak is almost never a problem with the chimney or skylight itself. It's a problem with the flashing, the metal pieces that seal the gap between your roof surface and the penetration. In Winnipeg, that flashing takes a beating:
- Freeze-thaw cycles, we get more than 50 freeze-thaw events a year in this city. Each one expands and contracts the metal and the roofing materials around it, working the sealant loose and opening hairline gaps that grow over time.
- Ice dams, when snow melts off your roof and refreezes at the eaves, it backs water up under the shingles and flashing. That water finds the path of least resistance, and chimney and skylight penetrations are exactly where it goes.
- Hail damage, May through September, hail can dent flashing, crack skylight seals, and bruise the asphalt shingles around the penetration. The damage isn't always visible from the ground.
- Age, flashing has a lifespan. After 15–20 years, the metal fatigues, the sealant dries out, and the rubber boots around vent pipes crack.
The result is the same: water gets in, stains your ceiling, rots your framing, and if left alone, damages the insulation and drywall. The fix is to find where the water is actually entering, not where it's showing up on your ceiling.
What's Included in the Repair
if you book a chimney or skylight leak repair with Roof Repair Winnipeg, what the job covers:
- On-roof inspection, we get up there and look at the actual flashing, the shingles around the penetration, the skylight frame, and the chimney chase. We don't diagnose from your living room.
- Leak detection, if the source isn't obvious, we use thermal imaging and water testing to trace the entry point. This is included in the diagnostic phase of the repair.
- Flashing repair or replacement, we re-seal, re-fit, or replace the metal flashing around the chimney or skylight. If the flashing is beyond saving, we replace it with new stepped or continuous flashing, properly integrated with the asphalt shingles.
- Sealant and boot replacement, we replace dried-out caulk and cracked rubber boots with fresh, UV-resistant sealant and new boots rated for Winnipeg winters.
- Skylight seal and frame work, we re-seal the skylight glazing, check the frame for rot, and repair or replace damaged seals.
- Ice dam mitigation, if ice dams caused the leak, we address the immediate backup and recommend the ventilation or de-icing work needed to stop it from recurring.
- Ceiling stain assessment, we'll tell you whether the interior stain needs attention and what the drywall repair will involve, so there are no surprises after we leave.
- Adjuster-ready documentation, if hail or storm damage is involved, we provide a damage report you can hand to your insurance adjuster.
The goal is a complete repair, not a patch. We fix the source, and we do it so it holds up to the next freeze-thaw cycle, the next hail season, and the next ice dam.
Chimney & Skylight Leak Repair Pricing in Winnipeg
Here's a breakdown of what drives the cost. Every number below is a range, not a quote, the final price varies a lot depending on job size, scope, and site conditions.
| Scope of Work | Typical Range |
|---|---|
| Re-sealing flashing and replacing caulk around a chimney or skylight | $250–$500 |
| Partial flashing repair, re-fitting one or two sections | $350–$700 |
| Full flashing replacement around a chimney or skylight | $600–$1,200 |
| Skylight seal replacement and frame re-sealing | $400–$900 |
| Boot replacement around vent pipes near the penetration | $150–$400 |
| Ice dam removal and de-icing work linked to the leak | $200–$800 |
| Interior drywall and ceiling stain repair (if you want it done) | $200–$800 |
A few things that push the price up:
- Roof pitch, a steep roof is harder and slower to work on, and that adds labour time.
- Number of penetrations, if you have two skylights and a chimney all leaking, the scope multiplies.
- Flashing condition, if the metal is corroded or the wood underneath is rotted, replacement costs more than a re-seal.
- Access, a second-storey roof with limited ladder access takes longer.
- Season, winter leak response involves ice and snow removal before we can even see the flashing, which adds time and cost.
A few things that bring the price down:
- Early detection, catch the leak after one rain event, and the damage is usually limited to the flashing itself.
- Simple scope, a single chimney with intact flashing just needs a re-seal, and that's the low end of the range.
- Insurance coverage, if hail or storm damage caused the leak, your policy may cover the repair. We provide the documentation your adjuster needs.
Free on-site estimate · no obligation
Our Repair Process
Here's exactly how a chimney or skylight leak repair works with us:
Book the inspection
Call or use the website to book. We serve all of Winnipeg and surrounding communities, including St. Vital, Charleswood, River Heights, Transcona, and the surrounding RM areas
On-roof diagnosis
We get up on the roof and inspect the flashing, the shingles, the skylight frame, and the chimney chase. If the source isn't obvious, we use thermal imaging and water testing to trace it. We don't guess, and we don't patch the ceiling and call it done
Honest quote
You get a written quote for the repair. It's the same person who inspected your roof, and it's the same person who'll do the work. We tell you directly if a repair is the smart move or if a replacement makes more sense. If we quote a repair, it's because a repair will actually hold
The repair
We do the work, re-sealing, re-fitting, or replacing flashing, replacing boots and sealant, and addressing any ice dam or ventilation issues that caused the leak. We use materials rated for Winnipeg winters
Water test and walkthrough
We test the repair with water before we leave, then walk you through what we did, what we found, and what to watch for. If your insurance claim is involved, you get the adjuster-ready report
Warranty and follow-up
The repair is backed by our workmanship warranty. If it leaks again, we come back. That's the deal
Why Choose Roof Repair Winnipeg
Small crew, honest pricing. We run deliberately lean. No call centre, no account managers, no showroom, no twelve-truck fleet. The person who answers the phone is the person who inspects your roof, writes your quote, and does the repair. That low overhead shows up in the price.
Repair-first quotes. Most Winnipeg roofers make their money on replacements. We make ours on fixing leaks properly. When we quote a chimney or skylight repair, it's because a repair is the right call. When a replacement is the right call, we tell you that too, but we won't sell you one you don't need.
Freeze-thaw local crew. We've worked every season this city has. We know what freeze-thaw does to flashing, what hail does to asphalt shingles, and what ice dams do to a roof penetration. That experience is built into every repair.
Storm response in 24–48 hours. If hail or storm damage caused your leak, we get to you fast. We contain the leak, document the damage, and give you an adjuster-ready report for your insurance claim. That speed keeps the water from doing real damage to your framing, insulation, and drywall.
No surprises. You get a written quote before we start. The price you're quoted is the price you pay. If we find something unexpected mid-job, we stop and talk to you before we proceed. No hidden charges, no "while we're up here" upsells.
Get Your Free Quote Today
If your chimney or skylight is leaking, don't wait for the next rain event. The longer water sits in your framing, the more the damage spreads, and the more the repair costs. Book a free quote with Roof Repair Winnipeg today. We'll get up on your roof, find the actual source of the leak, and give you an honest price to fix it. Small crew. Honest repairs. Fair prices. That's how we've built our name in Winnipeg.