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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
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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
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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
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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
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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
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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
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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
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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
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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.
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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
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Find Roofers in Chester

Global Home Exteriors, Inc.

4.8(

)

Flat, Foam or Single Ply Roofing - Repair- For BusinessAsphalt Shingle Roofing - Repair - For BusinessAsphalt Shingle Roofing - Install or Replace - For Business+2 more

Serving Chester, 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 !"

Response time3 days

106 neighbors recently requested a quote

Recommended by97%of homeowners

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Adam Quenneville Roofing and Siding, Inc.

4.7(

136

)

Asphalt Shingle Roofing - RepairRoof - Clean

Serving Chester, MA and surrounding areas

Approved

In business since 2004

Free estimates

Warranties offered

"They would not do the complete job that I needed, i.e., they would only do the exterior roofing work while I needed interior work done as well."

Response time10 hrs

54 neighbors recently requested a quote

Recommended by69%of homeowners

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East Coast Metal Roofing, LLC - Massachusetts

4.6(

104

)

Metal Roofing - Install or Replace

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

62 neighbors recently requested a quote

Recommended by92%of homeowners

Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For Business

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

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Power Home Remodeling

4.1(

546

)

Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairInspection - Roofing+4 more

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

2669 neighbors recently requested a quote

Recommended by84%of homeowners

Asphalt Shingle Roofing - Install or Replace

Serving Chester, MA and surrounding areas

Approved

In business since 1999

Free estimates

Emergency services offered

"Aaron Tircuit Excellent in improving my knowlege of roofing Outstanding ability to answer my questions. I signed two. Contractions immediately!!!"

Recommended by87%of homeowners

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ProEdge Remodeling - Roofing

4.3(

)

Asphalt Shingle Roofing - Install or Replace

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 rate97%

30 neighbors recently requested a quote

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Alliance Home Improvement, Inc.

4.5(

)

Asphalt Shingle Roofing - Install or Replace

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 rate93%

54 neighbors recently requested a quote

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Advanced Seamless Gutters

4.4(

210

)

Metal Roofing - Install or Replace

Serving Chester, MA and surrounding areas

Approved

In business since 1999

Free estimates

Emergency services offered

"The options and costs were explained well to me. The old gutters were removed without damage to my house. The old gutters were disposed of. The new gutters were neatly and professionally installed. They cleaned up after themselves. I was very pleased with the workmanship."

+63

Response time1 day

Response rate86%

92 neighbors recently requested a quote

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Showing 1-10 of 191

Roofing questions, answered by experts

Tar and gravel roofs last an average of 30 years, which is longer than the average lifespan of many other flat roofs. The gravel on top of the waterproof membrane helps protect the roof from UV damage and physical damage, so if you keep your roof drains clear and carry out annual roof inspections to catch issues early, you could see up to 40 years of useful life from your roof.

For homeowners who plan to stay in their homes for a long time or never want to have to deal with replacing a roof again, rubber roof shingles are likely worth the added investment amount over asphalt shingle varieties. While the initial cost of installing a rubber shingle roof will be significantly higher, their long life spans can be worth it in the long term. Consider the curb appeal of a rubber roof, though, as other roofing materials, like metal, can look better and offer even greater value.

If you’re building the roof trusses yourself, which isn’t recommended, it will be more affordable than buying pre-built trusses. Trusses cost more because they use the same amount of material, but you’ll also be paying for the labor, as well as the delivery to your home. However, if you’re having a contractor build the roof for you, then trusses will be less expensive, as the labor costs to build roof framing on-site will cost more.

An improperly installed skylight could potentially impact your roof's warranty. This happens because roofing penetration is necessary during skylight installation. Check your warranty information to verify. In most cases, having skylights professionally installed with proof that flashing is being done to specifications can be enough to preserve your roof's warranty.

Copper roofs last an average of around 100 years, making it one of the longest-lasting types of roofs. It’s significantly more expensive than an asphalt shingle roof, but it also lasts three to four times as long, providing great value for the money. You can extend the life of your copper roof by carrying out routine maintenance, like scheduling annual cleaning and roof inspections.

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.