Roof Replacement in Mendon, MA: Fixing Failing Shingles & Flashing on a 1958 Home

Project Summary

  • Location: Mendon, MA
  • Home: Built in 1958
  • Problem: Deteriorated shingles, failing & missing flashing, active leak risks
  • Solution: Full roof replacement with new decking repairs, underlayment, and flashing system
  • Result: Long-term protection, improved durability, and peace of mind
replaced roof by Master Roof

The Situation: An Aging Roof Reaching Its Limit

This Mendon, MA home, built in 1958, had a roofing system that had simply reached the end of its lifespan.


The homeowner was dealing with:

  • Worn, brittle shingles
  • Areas of failing and missing flashing
  • Visible vulnerabilities around roof penetrations


While there may not have been a catastrophic failure yet, the roof was at a tipping point—where small issues could quickly turn into major leaks.

The Inspection: What We Found

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

Once the Master Roof team got on-site and began evaluating the roof, the extent of the issues became clear:

  • Significant shingle deterioration reducing water protection
  • Improper and failing flashing around vents and key areas
  • Exposed and vulnerable penetrations (as seen in the photos)
  • Underlying areas at risk of water intrusion


After stripping the roof, it confirmed what we often see in homes of this age—hidden vulnerabilities that aren’t always visible from the ground.

The Fix: A Full Roof Replacement Done Right

To ensure the home was properly protected moving forward, Master Roof completed a full replacement with a focus on doing it right—not just fast.



Key steps included:

  • Full tear-off of old roofing materials
  • Inspection of roof decking and replacement where needed
  • Installation of high-quality synthetic underlayment (as shown in progress photos)
  • Proper sealing of all penetrations, including vent boots
  • Installation of new flashing system to eliminate weak points
  • Installation of new shingles for long-term durability
  • This comprehensive approach ensures every layer of the roofing system works together to protect the home.

The Result: A Roof Built for the Next Several Decades

With a brand-new roofing system in place, this Mendon homeowner now has:


  • Reliable protection against leaks
  • Properly sealed flashing and penetrations
  • A roof system designed to handle New England weather
  • Confidence knowing the job was done thoroughly


Instead of continuing to patch problem areas, the homeowner made a smart investment in a long-term solution.

Project Gallery

Old chimney with failing flashing
Newly flashed chimney and new roofing

Frequently Asked Questions

  • How do I know if I need a full roof replacement instead of a repair?

    If shingles are widely deteriorated and flashing is failing in multiple areas, a replacement is often more cost-effective than ongoing repairs.

  • What happens if flashing is missing or failing?

    Flashing protects the most vulnerable areas of your roof. Without it, water can easily enter and cause interior damage.

  • Why is underlayment important in a roof replacement?

    Underlayment acts as a secondary water barrier, protecting your home even if shingles are damaged.

  • Are roof penetrations like vents common leak points?

    Yes—vents, pipes, and other penetrations are some of the most common sources of leaks if not properly sealed.

  • How long does a new roof typically last in Massachusetts?

    With proper installation and materials, a new asphalt roof can last 20–30+ years depending on conditions.

Contact Us

Other Roofing Projects in Mendon & Surrounding Towns

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

Properly installed flashing and shingles around a chimney
April 28, 2026
Leaking roof in Hopkinton, MA? See how Master Roof repaired chimney flashing, sheathing, and gutters to stop leaks for good.
New roofing installed around a chimney
April 27, 2026
Leaking chimney in Holliston, MA? See how Master Roof rebuilt flashing and a cricket to stop water intrusion and protect this 1957 home.
Home with an old roof
March 28, 2026
Explore this Shrewsbury, MA roof replacement case study featuring GAF Timberline HDZ shingles, Deck-Armor, StormGuard, chimney flashing, and venting improvements.
Image of house in Upton, MA, before roof replacement
March 28, 2026
Master Roof replaced a 1994 roof in Upton, MA using GAF Timberline HDZ, Deck-Armor, and StormGuard, including skylight replacement and flashing upgrades.
1958 Home with Master Roof truck in the driveway
March 28, 2026
Master Roof replaced a 1958 Burlington, MA roof using GAF Timberline HDZ, Tiger Paw, and StormGuard, fixing skylights, flashing, and wood rot issues.
Older home getting a new roof
February 25, 2026
Master Roof replaced a storm-damaged 1894 Springfield home roof, upgrading decking, flashing, and gutters to meet Massachusetts code.
SHOW MORE