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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 BusinessAsphalt Shingle Roofing - Repair - For BusinessSealant for Roof - Apply- 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
152 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
58 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
74 neighbors recently requested a quote
Recommended by92%of homeowners
Avatar for Overstate Roofing Services Inc.
Overstate Roofing Services Inc.
4.2(
80
)
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
1719 neighbors recently requested a quote
Recommended by1%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 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%
12 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%
17 neighbors recently requested a quote
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Roofing FAQs, answered by experts

Underlayment is used between existing shingles and a new metal roof to prevent friction and wear from the shingle granules on the underside of the metal. The underlayment also helps prevent water intrusion and allows expansion and contraction without wearing away at the roofing material.

A roof replacement will usually include removal of your old roof, shingle replacement, and a new roof underlayment, but it may only include adding new shingles if you’re layering new shingles over the old shingles. If you have signs of roof leaks or your roofer finds water damage to the roof decking underneath your old roof, it can also include replacement of the OSB or plywood decking that lays over your rafters and supports the roofing material above.

The formula for calculating how many squares of roofing you need is pretty easy. Take the total amount of square footage and divide it by 100. With this formula in mind, a 2,000-square-foot roof would require 20 squares of roofing material to adequately cover it.

Fall is widely considered the best time of year to replace a roof. The moderate temperatures are ideal for roofing crews to work and for new shingles to seal properly. Additionally, autumn weather is often drier, reducing the risk of weather-related delays compared to the rainier spring season.

While spring is also a viable option, the higher chance of rainfall can slow down the project. The main drawback to a fall installation is that it's the peak season for roofers, which can lead to higher prices and scheduling challenges.

To potentially save money, you could consider scheduling your roof replacement during the summer or winter off-seasons. However, both seasons have significant disadvantages. Extreme summer heat can make shingles too soft to handle, while winter's cold, snow, and ice can create dangerous working conditions and prevent shingles from sealing correctly, as they typically require temperatures above 40-45°F.

The best kind of tarp for a roof is one that will stand up to the elements, weather, and sun. Viny roof tarps are known for their durability and resistance to water, tears, and mold—making these tarps a good choice for use in winter conditions and the summer sun. Polyethylene tarps are also quite durable and waterproof.

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.