Roof leak repair
A Small Leak Is Never Small for Long
That faint ceiling stain after a rainy weekend in Oak Bluffs? It’s the last stop on a journey that started somewhere up on the roof — often nowhere near where the water shows up inside. Water tracks along rafters and sheathing before it drips, which is why “caulk where it drips” repairs fail and why leak-chasing is a skill, not a guess.
We trace leaks to their true source: lifted or cracked shingles, failed pipe boots, rusted valley metal, tired chimney and wall flashing, clogged dead valleys, or skylights that were never flashed correctly in the first place. Then we fix the source properly — matching materials where it matters and photographing the work so you can see exactly what was done.
Storm & Wind Damage: What to Do First
Nor’easters and hurricane-season winds are part of Vineyard life. When a storm lifts shingles in Chilmark or drops a limb on a Vineyard Haven roof, the first 48 hours matter most. Here’s our process:
- Emergency tarping — we secure the damaged area fast so one storm doesn’t become two claims.
- Photo documentation — every damaged area photographed and written up for your insurance conversation.
- Honest scope — if it’s a repair, we say so. If the storm exposed a roof at the end of its life, we’ll show you why.
- Permanent repair — wind-rated materials installed to the current MA building code, not a patch that waits for the next gust.
Repairs We Handle Every Week
Missing and wind-lifted shingles, roof leak repair around chimneys and plumbing vents, flashing repair and replacement, valley rebuilds, ridge cap repairs, leaking skylights, cedar shingle repairs and blending, soffit and fascia damage, and small structural fixes where rot has started. If water is getting in — from Edgartown to Aquinnah, and yes, Chappaquiddick too — we’ve almost certainly fixed the exact problem before.
Repair or Replace? The Honest Answer
Our rule of thumb: localized damage on a roof under ~15 years old is usually worth repairing. Recurring leaks on an older roof usually aren’t — you end up paying for the same square feet twice. And because insurers now scrutinize roof age, sometimes the repair that “saves money” costs you at renewal time. When it’s a close call we price both paths in writing — the repair and the full replacement — so you can decide with real numbers.
While we’re up there, we’ll also flag anything else that shortens roof life: clogged or sagging gutters (see our seamless gutter installation), blocked ventilation, or trim that’s letting water behind the fascia.
Roof Repair FAQs
How fast can you repair my roof?
In most cases we offer same-week repair appointments anywhere on Martha’s Vineyard. After major storms we triage: emergency tarping first to stop water, then permanent repairs as materials and weather allow.
Will you help with my insurance claim?
We document storm and wind damage with clear photos, tarp the roof to prevent further damage, and give you a written scope you can bring to your insurance conversation. We can’t file the claim for you, but we make sure you walk into it with real evidence.
Should I repair or replace my roof?
If the damage is localized and the roof is under about 15 years old, a repair usually makes sense. If leaks keep coming back or the roof is 15+ years old, replacement is often the better investment — and insurers increasingly look at roof age. We’ll give you an honest written answer either way.
