If you’re planning a roof replacement or repair in Massachusetts, finding the right roofing contractor is essential. With the region’s harsh winters, coastal storms, and humid summers, your roof takes a beating year-round. Choosing the right roofing company can make the difference between a secure, long-lasting roof and one that needs constant repairs.

To help you make a smart hiring decision, we’ve compiled a list of the most important questions to ask a roofer before hiring in Massachusetts. These questions will give you peace of mind and help ensure the job is done to code, on time, and with high-quality materials.

Why Asking the Right Questions Is Critical in Massachusetts

Massachusetts has strict building codes and unpredictable weather patterns. From Nor’easters to heavy snowfall, your roof must be able to withstand extreme conditions. That’s why it’s important to hire a roofer who not only has strong references, but also understands local codes, weather challenges, and permitting requirements specific to towns like Boston, Newton, Woburn, and Cape Cod.

Whether you’re in the suburbs of Greater Boston or along the New Hampshire border, these questions will help you hire a roofing contractor you can trust.

1. Are You Licensed and Insured in Massachusetts?

This is the first and most important question to ask. In Massachusetts, roofing contractors must be licensed by the state and carry general liability and workers’ compensation insurance. This protects you from liability in the event of accidents or property damage.

Ask for their Massachusetts Construction Supervisor License (CSL) or Home Improvement Contractor (HIC) number, and verify their insurance coverage before any roofing work begins.

2. What Type of Warranty Do You Offer?

Weather in Massachusetts can be rough on roofing systems. That’s why you need both a material warranty and a workmanship warranty.

• Material warranties cover defects in the roofing material, often offered by manufacturers like GAF or CertainTeed.
• Workmanship warranties cover errors in the roof installation process and are provided by the roofer.

Ask how long each warranty lasts, what’s covered, and whether they’ll be honored in Massachusetts. Olympic Roofing, for example, is a GAF Master Elite Contractor offering industry-leading warranties to local clients.

3. Can You Provide Local References?

Massachusetts towns can vary widely in architecture, building codes, and homeowner preferences. Ask for local references, especially from homeowners in your area. This way, you can gauge the roofer’s familiarity with regional materials, municipal requirements, and the performance of their past roofing jobs in similar conditions.

4. What Roofing Materials Do You Recommend for New England Weather?

Not all shingles and roofing systems are suitable for New England. Ice dams, heavy snowfall, and high winds are common in cities like Worcester, Salem, and Lowell.

A qualified roofing contractor should explain which roofing materials—like architectural asphalt shingles, metal roofing, or rubber membrane for flat roofs—will work best for your property and the local climate.

5. Will You Remove My Old Roof?

It’s tempting to allow a contractor to install new shingles over the existing roof to save money, but this can shorten the lifespan of your roof and conceal issues like water damage or rotted decking.

In Massachusetts, with its freeze-thaw cycles and heavy snow loads, a full roof tear-off is almost always the better option. Be sure to confirm that the contractor plans to remove the old roof entirely.

6. How Will You Protect My Property?

Ask how your roofing company will protect your home’s siding, landscaping, and driveway—especially during a full tear-off. In Massachusetts, homes are often closer together, so careful debris management is crucial. Also ask how they will dispose of old materials and clean up after the job is complete.

7. Do You Pull Permits and Follow Massachusetts Building Codes?

Permits are required for most roofing projects in Massachusetts. Each town has its own inspection process, so it’s important to work with a roofer who understands local requirements. Ask if the company will handle the permit process.

A reputable contractor, like Olympic Roofing, will know how to navigate Massachusetts building codes and ensure your roofing job passes all required inspections.

8. Who Will Be Onsite for the Roofing Work?

Will the roofer you hire oversee the roof installation, or will they subcontract the work to another crew? Ask who will be present on the job site and whether a foreman or project manager will be supervising.

This is especially important in Massachusetts, where homes may have steep rooflines or historic architectural details that require extra attention.

9. What’s the Project Timeline?

Get a clear timeline for your roofing project. Roofing season in Massachusetts is limited, with spring through early fall being the busiest time of year. Ask when they can start, how long it will take, and how they handle delays due to weather.

10. Will You Install Proper Flashing and Drip Edge?

Flashing and drip edge installation is essential to keeping moisture out of your roof. Improper flashing around chimneys, skylights, and valleys is a leading cause of roof leaks in Massachusetts homes.

Ask the roofer how they handle flashing and whether they use metal drip edge along all roof edges as part of their standard practice.

11. What Happens If You Find Rot or Structural Damage?

Massachusetts homes, especially older ones, may have rotted decking, insufficient ventilation, or framing issues hidden beneath the surface. Ask your roofer how they address surprises during the job. Will they notify you first? How will they price the repairs?

The contractor should have a clear, documented process for handling unexpected issues, including change orders.

12. Can I Get a Detailed, Written Estimate?

Always ask for a written estimate before signing any contracts. Your estimate should include:

• Labor and materials
• Roof type and materials selected
• Timeline
• Payment schedule
• Permits and inspection details
• Warranty offered

Make sure the quote reflects Massachusetts-specific factors like regional labor costs and compliance with state codes.

Final Thoughts

Choosing the right roofing contractor in Massachusetts starts with asking the right questions. Whether you’re in Andover, Peabody, Waltham, or another part of the state, this guide will help you confidently evaluate your options and avoid costly mistakes.

Olympic Roofing has proudly served homeowners across Massachusetts, New Hampshire, and southern Maine for over 50 years. As a trusted, licensed, and insured roofing company, they welcome your questions and provide transparent, reliable answers every step of the way.

Before starting your next roofing project, take the time to ask these essential questions to ask a roofer before hiring. You’ll save money, avoid headaches, and get the quality roofing work your home deserves.