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TRUSTED BY CHESTERFIELD, MA HOMEOWNERS

  • Average homeowner rating star icon4.3
    Average homeowner rating
  • Verified reviews icon168
    Verified roofing services reviews

Top-Rated Roofers in Chesterfield - Updated Nov 2026

Avatar for Global Home Exteriors, Inc.
Global Home Exteriors, Inc.
4.8(
86
)
Flat, Foam, or Single Ply Roofing - Install or Replace- For BusinessSealant for Roof - Apply- For BusinessAsphalt Shingle Roofing - Repair - For Business+2 more

Serving Chesterfield, MA and surrounding areas

Approved

In business since 2017

Free estimates

Emergency services offered

"I had a leak that can be seen from a ceiling. Called several roofing companies and got no reply back. Used home advisor and have Andrea called me and scheduled the visit promptly for Freddy to come and check the leak. Freddy was very professional, identified the leak that was due to improper seal of one of the skylights and fixed it right away. He also checked my other skylights and some had the same problem which he fixed. Freddy checked my roof for issues and provided tips for maintenance so it can last long. Definitely will recommend Global Home Improvement, Inc as a honest and very professional company !"
Roof Replacement
Roof Underlayment
Roof Installation
Roof Prep & Install
Shingle Installation

+1

Response time3 days
162 neighbors recently requested a quote
Recommended by97%of homeowners
Avatar for Adam Quenneville Roofing and Siding, Inc.
Adam Quenneville Roofing and Siding, Inc.
4.7(
136
)
Asphalt Shingle Roofing - RepairRoof - Clean

Serving Chesterfield, MA and surrounding areas

Approved

In business since 2004

Free estimates

Warranties offered

"Scott (the leader) Lewis and Davison did a stellar job on my 2 story home and garage. They go the extra mile! Have hired lots of folks who have done good work but this team I would give 10 stars to. Hope they are available again next fall!!! Very grateful."
Roof repair
Repairs
Roof maintenance.
New roof
Asphalt shingles, new roof.

+1

Response time10 hrs
52 neighbors recently requested a quote
Recommended by69%of homeowners
Avatar for East Coast Metal Roofing, LLC - Massachusetts
East Coast Metal Roofing, LLC - Massachusetts
4.6(
104
)
Metal Roofing - Install or Replace

Serving Chesterfield, MA and surrounding areas

Approved

In business since 2015

Free estimates

Warranties offered

"After a great deal of research into different metal roofing companies, we decided to call East Coast Metal Roofing. Dave Harrison came to our house, walking us through all the steps and answering whatever questions we had. We felt very good about our decision. The roofing team arrived earlier this past week. I didn't know that sort of worth ethic was still out there, but we were incredibly impressed! The care taken to protect the home and surrounding features, the constant clean up and the amazing skill to put our roof on so beautifully. Neighbors have commented on what a beautiful roof it is and we agree! They finished in a couple days and that night the rains came! No more worrying about a compromised roof! Thank you, Dave! Please convey our thanks to all members of the team at ECMR that made this possible. We are beyond thrilled with our decision and highly recommend ECMR to anyone contemplating a metal roof. Well worth the investment in our home."
Halifax, MA - Dawn Gray Aluminum Shingle
Griswold, CT - Dawn Gray Aluminum Shingle
Southborough, MA - Black Aluminum Shingle
Rindge, NH - Classic Brown Aluminum Shingle
Webster, MA - Black Aluminum Shingle

+155

Response time2 days
76 neighbors recently requested a quote
Recommended by92%of homeowners
Avatar for Express Home Restoration
Express Home Restoration
5.0(
10
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair - For Business

Serving Chesterfield, MA and surrounding areas

Approved

In business since 2024

Free estimates

Emergency services offered

We pride our company on reliability, great communication, integrity, and quality work. We are experts in our trade and will do our best to keep you as educated as we can on your particular task or project. We look forward to earning your business! Book with us online or feel free to give us a call today! \n

Roof Projects
Roof Projects
Roof Projects
Roof Projects
Roof Projects

+44

Response time4 hrs
Response rate93%
5 neighbors recently requested a quote
Avatar for Overstate Roofing Services Inc.
Overstate Roofing Services Inc.
4.2(
79
)
Asphalt Shingle Roofing - RepairFlat, Foam or Single Ply Roofing - RepairSealant for Roof - Apply+10 more

Serving Chesterfield, MA and surrounding areas

Approved

In business since 2025

Free estimates

Emergency services offered

"I have to commend these guys and the job they did with my roof. I had a partially collapsed roof from the snow and ice buildup on my roof. I needed the repair done urgently and withing budget. I got may quotes on the job with some outrageous bidding to be honest. Overstate gave me a fair price and told me exactly what needed to be done. Within a week the job was completed and my home is leakproof again."
Roof replacement
Roof replacement
1837 neighbors recently requested a quote
Recommended by1%of homeowners
Avatar for SOS Powerwash
SOS Powerwash
5.0(
12
)
Roof - Clean

Serving Chesterfield, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2022

Free estimates

Small jobs welcome

"My house and roof look fantastic. The chemical used for treating the moss on a portion of my roof also affected some of my surround plants on the ground. I'm sure they will come back fine next spring. It was worth it to have a clean house and roof."
What We Do...
What We Do...
What We Do...
What We Do...
Front Steps

+42

Response time7 hrs
Response rate97%
14 neighbors recently requested a quote
Avatar for Alliance Home Improvement, Inc.
Alliance Home Improvement, Inc.
4.5(
27
)
Asphalt Shingle Roofing - Install or Replace

Serving Chesterfield, MA and surrounding areas

Approved

In business since 2006

Free estimates

Warranties offered

"Entire process exceeded my expectations from the initial contact I had with Alliance to the completion of the project. The proposal I received from Keith provided the level of detail I was looking for and he did a great job in going over the siding products Alliance offered to detailing all the necessary steps in the process. The installation process went very smoothly and was completed in a timely manner. The crew led by Serg were extremely professional, knowledgeable and focused. I could not be happier with the work they did and Serg kept me updated on how the project was progressing and was quick to reach out to me with any questions he had on the proposed installation approach. Therefore, I would recommend Alliance for any home improvement needs that you may need addressed. Lastly, I was so satisfied with the siding installation Alliance did I am now having them replace the two entry doors to my garage. Thank you again Sergiy, Keith, Serg and the rest of the installation crew. CFP Sr."
Home Improvements
Home Improvements
Home Improvements
Home Improvements
Home Improvements

+37

Response time10 hrs
Response rate93%
22 neighbors recently requested a quote
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Roofing FAQs, answered by experts

Roof underlayment usually lasts as long as the roofing material that covers it, as it’s not directly exposed to the elements. In most cases, roofing companies will replace the underlayment each time they install a new roof. In some cases, particularly with slate, clay, or certain metal roofs that can last 50 to 100 years, your underlayment may require replacement within that timeframe, especially if you start to notice roof leaks.

Whether a metal or shingle roof is better for you depends on your preferences. Standing seam metal roofs require little to no maintenance, but if you install a screw-down metal roof where the fasteners are exposed, the gaskets on the fasteners will dry rot and need to be replaced. Generally, screw-down metal roofs need to be re-screwed every 15 to 20 years.

Metal roofs are energy-efficient and have extended warranties, while asphalt shingles are less durable than most. They tend to lose color and get damaged over time, and absorb heat from the sun.

It’s always a good idea to have a lawyer review any legally binding contract before signing, including roofing contracts. Most contracts have straightforward language that’s easy to understand, but getting advice from an attorney before signing could save you from being locked into a contract you don’t want to move forward with. Having a lawyer review your contract can also help protect you if your roofing professional defaults on their side of the agreement.

The material and frequency of maintenance are the biggest factors for determining the longevity of your shingles, not the color. For instance, luxury asphalt shingles can last 30 years or even longer, while slate tiles have an impressive lifespan ranging from 75 to 100 years. That said, lighter-colored shingles can help reduce your energy costs in the summertime.

While it’s technically possible to repoint a chimney without scaffolding, it’s not recommended, especially for taller chimneys. Scaffolding provides a stable platform that allows for safer and more precise work. Without it, you might find yourself in a risky situation, and the quality of the repointing could suffer.

The Chesterfield, MA homeowners’ guide to roofing services

From average costs to expert advice, get all the answers you need to get your job done.