Get matched with top roofers in Chester, MA

Enter your zip and get matched with up to 5 pros

Need a pro for your roofing project in Chester, MA?

Select your specific project to find the pro for you.

TRUSTED BY CHESTER, MA HOMEOWNERS

4.2
Average homeowner rating
53
Verified roofing services reviews

Verified Reviews for Roofing pros in Chester, MA

*The Angi rating for Roofing companies in Chester, MA is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Roofing needs.

*The HomeAdvisor rating for Roofing companies in Chester, MA is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Roofing needs.

Last update on October 08, 2025

Reviewed in October 2025
We had a leak in our roof, and most of the roofers looked at it and told us we would need a new roof. We had Jared come out, and he was able to plug the leak for much less money. He also did a variety of smaller plumbing projects that we are very happy with. We plan on having him back for more...
SmithCraft Land & Home
Request a quote
Reviewed in August 2025
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.
SOS Powerwash
Request a quote
Reviewed in December 2023
Jim Flannery and his crew are fantastic to work with. His pricing is fair and competitive and his work is exceptional. He helped my family with a job and was able to squeeze us in last minute with his crew working on a Sunday just so we could get our roof fixed quickly. After they were...
Peak Performance Roofing LLC
Request a quote
Reviewed in November 2023
We had our roof replaced by this company. The workers were very professional and respectful to the property. They stripped and put on the new shingles in a short amount of time and when they were finished they cleaned up the area spotless.
Dave Miner Exterior Home Improvements LLC
Request a quote
Reviewed in January 2023
I needed repairs done to my garage including a new roof and a new roof on my house. Eli contacted me and came to look at the job. He gave me a very reasonable quote for the work he could do. He is very friendly, professional and honest. He is not a roofer but his brother, Andrew, is (Greenroof...
EZ Restore
Request a quote
Reviewed in July 2022
Jake and the crew did a great job just like he said and he rip off my roof and put a pich roof over my addition they were friendly fast and cleaned up everything when was done we will be using him for all our roofing needs thankz you again
Dependable Roofing
Request a quote
Reviewed in June 2022
Paul and his son Gabe did a great job on my roof. I also had to have a new electrical box put in and they got me an electrician. They were just wonderful. I would recommend Paul and his son Gabe highly. The final job turned out great. Carol Brzys
New Vision Construction Services LLC
Request a quote
Reviewed in September 2021
I was very impressed with SageWood. In every aspect of my dealings with SageWood the owner was involved. He was very through, and communicated well; from the estimate trough the clean up. I had six skylights replaced, my roof removed, and the new roof installed in one day! Before they started I...
SageWood Home Exteriors
Request a quote
Reviewed in September 2021
I had a good experience hiring this company. My roof looks great at a price I can live with. They were very knowledgeable and informative throughout the entire process. The project started on time and finished on schedule.
Exterior Construction, Inc.
Request a quote
Reviewed in June 2021
We are so impressed by RhinoBack roofing and it all started with my initial phone call to the office (Lisa) to schedule an estimate. Initially Ed came to our home and spent a reasonable amount of time talking about our options, pricing and quality of products. We enjoyed his professionalism and...
Rhino-Back Roofing
Request a quote

Find Roofers in Chester

Global Home Exteriors, Inc.

4.8(

)

Serving Chester, MA and surrounding areas

Approved

In business since 2017

Free estimates

Emergency services offered

"Very prompt and organized. Andrea came out during the day while they were working on the roof to check on progress and to see if there were any questions. She also followed up by email to see if we had any questions and was very transparent on the extra cost of having to replace some of the decking. Will definitely use them again in the future if need be!"

Response time3 days

157 neighbors recently requested a quote

Recommended by97%of homeowners

Request Quote

Adam Quenneville Roofing and Siding, Inc.

4.7(

136

)

Serving Chester, MA and surrounding areas

Approved

In business since 2004

Free estimates

Warranties offered

"We have gone to Adam over the years for roof repairs, roof shampoo and now gutter covers. Always quick and efficient with quality work. Weâ ll be calling Adam when itâ s time to replace the roof in a few years."

Response time10 hrs

43 neighbors recently requested a quote

Recommended by69%of homeowners

Request Quote

East Coast Metal Roofing, LLC - Massachusetts

4.6(

104

)

Serving Chester, MA and surrounding areas

Approved

In business since 2015

Free estimates

Warranties offered

"The cost of metal roof is more than asphalt but this roof comes with 50 year guarantee. Since this is our third roof , I wish we had this option years ago. Roof looks great"

Halifax, MA - Dawn Gray Aluminum Shingle

Griswold, CT - Dawn Gray Aluminum Shingle

Southborough, MA - Black Aluminum Shingle

Rindge, NH - Classic Brown Aluminum Shingle

+155

Response time2 days

57 neighbors recently requested a quote

Recommended by92%of homeowners

Serving Chester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 1988

Free estimates

Warranties offered

"Paul came by to install solar powered vent and repair chimney leak and finish Velux install. All went well and very polite people."

+13

Request Quote

Power Home Remodeling

4.1(

546

)

Serving Chester, MA and surrounding areas

Approved (Corporate)

In business since 1992

Free estimates

Warranties offered

"The Power Home Remodeling crew were very professional, fixed my roof in timely mater, came on time, cleanup excellent and now i hve beautiful new roof."

+20

3532 neighbors recently requested a quote

Recommended by84%of homeowners

Serving Chester, MA and surrounding areas

Approved

In business since 1999

Free estimates

Emergency services offered

"Alex is outstanding. The entire experience with Long Roofing is outstanding."

Recommended by87%of homeowners

Request Quote

ProEdge Remodeling - Roofing

4.3(

)

Serving Chester, MA and surrounding areas

Approved

In business since 1961

Free estimates

Credit card accepted

"Very satisfied. I built my own home that Jason, Eddie and David worked in. Could not be happier with there work and the windows. Would highly recommend them."

Recommended by85%of homeowners

Serving Chester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2022

Free estimates

Small jobs welcome

"They called me and came over the same day. The deck looks great and they worked very hard."

+42

Response time7 hrs

Response rate91%

30 neighbors recently requested a quote

Request Quote

Alliance Home Improvement, Inc.

4.5(

)

Serving Chester, MA and surrounding areas

Approved

In business since 2006

Free estimates

Warranties offered

"Hard working crew, professional , polite answered all questions. Once siding completed removed unused material and cleaned the area. definitely recommend"

+37

Response time10 hrs

Response rate92%

51 neighbors recently requested a quote

Request Quote

Advanced Seamless Gutters

4.4(

210

)

Serving Chester, MA and surrounding areas

Approved

In business since 1999

Free estimates

Emergency services offered

"great product just still waiting for them to come adjust roof heat cable pinched under new gutter"

+63

Response time1 day

66 neighbors recently requested a quote

Recommended by92%of homeowners

Request Quote

...

Showing 1-10 of 193

Roofing questions, answered by experts

Unfortunately, there’s no definitive answer to this question, but the wind rating of your shingles will give you a good idea of what wind speeds can damage your roof. If you’re concerned about damage, inspect your roof following windy conditions to look for signs of wind damage to your shingles. When in doubt, consider hiring a professional who fixes roofs to carry out an expert inspection. Remember that hurricanes, tropical storms, and tornadoes are likely to cause the most damage, but even severe thunderstorms can bring winds that compromise your roofing system.

There are several signs that indicate you’ll need new underlayment. Clear signs include missing or damaged roofing and exposing the underlayment to the elements. Additionally, if you notice water damage in your home by the roof after a storm, it could indicate that your underlayment may need to be replaced. If your gutters aren’t draining properly, it could also lead to rotting or water damage to the underlayment.

Heated roofs are a preventative measure and don’t have an outsized effect on your home’s value, so there is no definitive answer to this question. If you diligently monitor your roof in colder months, ensuring there is never snow or ice buildup then no, maybe they aren’t worth it. However, who really watches their roof every day or goes out in freezing weather to rake the roof? For most people worried about roof damage in the winter, heated roofs are a good investment.

If you choose tile for your roof, take the time to hire a true tile professional. Look at trusted online review sites to find a top-rated roofing contractor. This helps you zero in on great contractors while avoiding ones who bait and switch you with fluctuating bids.

After you’ve narrowed down a few great candidates with reasonable bids, there are some important questions to ask roofers before you hire. Be sure they are licensed, bonded, and insured before signing a contract. Once you find a roofer who checks off all your boxes, you’re ready to get your project started.

Tile roofing is durable, fire-resistant, and energy-efficient. It also adds aesthetic appeal and, with proper maintenance, can last 50-100 years.

The Chester, MA homeowners’ guide to roofing services

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

See all articles

Mizuki Hisaka
•
Mar 5, 2026Mar 5, 2026
How Much Does Roof Replacement Cost? [2026 Data]
A new roof improves curb appeal, increases home value and keeps your living space protected from the elements. Learn about average roof replacement costs to set your budget.
Deane Biermeier
•
Mar 17, 2026Mar 17, 2026
How Much Does Roof Repair Cost? [2026 Data]
The average cost of roof repair for U.S. homeowners averages between $386 and $1,875. Learn what factors can affect roof repair costs.
Dan Simms
•
May 30, 2026May 30, 2026
How Much Does It Cost to Tarp a Roof? [2026 Data]
Wondering about the cost to tarp a roof after a large storm or before a major roof renovation? We'll break it down by size, style, and scenario.
Rachel Hoffman
•
Jul 9, 2026Jul 9, 2026
Parts of a Roof: Ultimate Guide to Roof Anatomy
All of the parts of your roof work together to protect your home. Learn the anatomy of a roof and how each part functions.
Brionna Farney
•
Jul 9, 2026Jul 9, 2026
How to Build a Roof For Your Home, From Start to Finish
Building a roof is a serious but rewarding project. If you're up to the task, use this step-by-step guide to learn how to build a roof without the help of a contractor.
Dan Simms
•
Jul 9, 2026Jul 9, 2026
Who Can I Hire to Tarp My Roof?
Roof leaks are an emergency, so knowing who can tarp your roof quickly and correctly can save you from major water damage if you ever experience a leak.