Chimney Leak Repair in Holliston, MA: Rebuilding a Failing Cricket & Flashing System

Project Summary

  • Location: Holliston, MA
  • Home: Built in 1957
  • Problem: Active chimney leak caused by failed flashing and deteriorating shingles
  • Solution: Rebuilt chimney cricket and re-roofed surrounding area
  • Result: Leak fully resolved with long-term water protection
replaced roof by Master Roof

The Situation: A Persistent Chimney Leak

The homeowner in Holliston, MA began noticing signs of a leak around their chimney—something that can quickly escalate if not addressed.


Built in 1957, the home’s roofing system had aged over time, and the area around the chimney had become a weak point. The flashing had failed, and the surrounding shingles were breaking down, allowing water to penetrate during rainstorms.


Like many homeowners, what started as a small issue had the potential to turn into much bigger (and more expensive) damage if left untreated.

The Inspection: What Was Causing the Leak

After a thorough inspection, the Master Roof team identified two primary issues:

  • Failed chimney flashing – no longer creating a watertight seal
  • Worn and deteriorating shingles around the chimney
  • Improper water diversion due to an ineffective or aging cricket system

Without proper drainage, water was pooling and pushing directly toward the chimney—one of the most vulnerable areas on any roof.

The Fix: Rebuilding Protection Where It Matters Most

To fully resolve the issue and prevent future leaks, Master Roof took a comprehensive approach:

  • Removed damaged shingles and old flashing around the chimney
  • Rebuilt the chimney cricket to properly divert water away
  • Installed new underlayment for added moisture protection
  • Re-roofed the area with high-quality shingles
  • Installed new flashing to create a tight, long-lasting seal

This wasn’t just a patch—it was a targeted rebuild designed to eliminate the root cause of the leak.

The Result: A Dry Home & Long-Term Peace of Mind

With the new cricket, flashing, and roofing system in place, the chimney is now fully protected from water intrusion.

The homeowner can move forward with confidence knowing:

  • The leak has been completely resolved
  • Water is now properly directed away from the chimney
  • The repair was done right the first time

Why This Matters

Chimney leaks are one of the most common roofing issues—and one of the most overlooked.

Without proper flashing and water diversion (like a cricket), even a small leak can lead to:

  • Interior water damage
  • Mold growth
  • Structural deterioration

Addressing the root cause—not just the symptoms—is what makes the difference between a temporary fix and a lasting solution.

Project Gallery

Old chimney with failing flashing
Newly flashed and flashed chimney

Frequently Asked Questions

  • What causes leaks around a chimney?

    The most common causes are failed flashing, deteriorated shingles, or poor water drainage. Chimneys interrupt the roofline, making them especially prone to leaks if not properly sealed.

  • What is a chimney cricket and why is it important?

    A cricket is a small peaked structure built behind a chimney to divert water away. Without it, water can pool and increase the risk of leaks.

  • Can chimney leaks be fixed without replacing the entire roof?

    Yes. In many cases, like this one, the issue can be resolved by repairing the flashing, rebuilding the cricket, and replacing the surrounding shingles.

  • How do I know if my chimney flashing has failed?

    Signs include water stains near the chimney, visible gaps or rust in flashing, or leaks during rainstorms.

  • How much does a chimney leak repair cost in Massachusetts?

    Costs vary depending on the extent of damage, but targeted repairs are typically far more affordable than a full roof replacement—especially when caught early.

Contact Us

Other Roofing Projects in Holliston & Surrounding Towns

At Master Roof, we offer exceptional residential roofing services across Holliston including roof replacement, repairs, attic ventilation, chimney flashing, skylight installations, roof maintenance, and assessments. Here are some other Master Roof projects in the area.

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