Top-rated roofers.

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

  • Average homeowner rating star icon4.2
    Average homeowner rating
  • Verified reviews icon53
    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

Find Roofers in Chester

Avatar for Global Home Exteriors, Inc.
Global Home Exteriors, Inc.
4.8(
86
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceFlat, Foam, or Single Ply Roofing - Install or Replace+5 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 !"
Roof Replacement
Roof Underlayment
Roof Installation
Roof Prep & Install
Shingle Installation

+1

Response time3 days
170 neighbors recently requested a quote
Recommended by97%of homeowners
Request Quote
Avatar for Adam Quenneville Roofing and Siding, Inc.
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."
Roof repair
Repairs
Roof maintenance.
New roof
Asphalt shingles, new roof.

+1

Response time10 hrs
45 neighbors recently requested a quote
Recommended by69%of homeowners
Request Quote
Avatar for East Coast Metal Roofing, LLC - Massachusetts
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
Webster, MA - Black Aluminum Shingle

+155

Response time2 days
57 neighbors recently requested a quote
Recommended by92%of homeowners
Request Quote
Avatar for JP Carroll Roofing
JP Carroll Roofing
5.0(
10
)
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."
JP Carroll Roofing
JP Carroll Roofing
JP Carroll Roofing
JP Carroll Roofing
JP Carroll Roofing

+13

Request Quote
Avatar for Power Home Remodeling
Power Home Remodeling
4.1(
546
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairMetal Roofing - Install or Replace+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."
GAF Fortitude Roof
GAF Fortitude Roof
GAF Fortitude Roof
GAF Fortitude Roof
GAF Fortitude Roof

+20

3339 neighbors recently requested a quote
Recommended by84%of homeowners
Request Quote
Avatar for Long Home
Long Home
4.3(
184
)
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
Request Quote
Avatar for ProEdge Remodeling - Roofing
ProEdge Remodeling - Roofing
4.3(
47
)
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."
Asphalt Shingle Roofing
Asphalt Shingle Roofing
Recommended by85%of homeowners
Request Quote
Avatar for SOS Powerwash
SOS Powerwash
5.0(
12
)
Roof - Clean

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."
What We Do...
What We Do...
What We Do...
What We Do...
Front Steps

+42

Response time7 hrs
Response rate91%
28 neighbors recently requested a quote
Request Quote
Avatar for Alliance Home Improvement, Inc.
Alliance Home Improvement, Inc.
4.5(
26
)
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"
Home Improvements
Home Improvements
Home Improvements
Home Improvements
Home Improvements

+37

Response time10 hrs
Response rate92%
51 neighbors recently requested a quote
Request Quote
Avatar for Advanced Seamless Gutters
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."
BASEMENT RE-FINISHING
MOLD CERTIFICATION
Hatchway
Footer
Hatchway Foundation Walls

+63

Response time1 day
67 neighbors recently requested a quote
Recommended by92%of homeowners
Request Quote
...
Showing 1-10 of 190
Roofing questions, answered by experts

Yes, roofers can repair and replace roof trusses. In fact, because trusses are such an important part of your roof’s structure, it’s best to have a roofing contractor deal with a damaged truss. If you try to fix the problem without the right skills or knowledge, your roof could sustain further damage or even collapse.

You shouldn’t put a new roof underlayment over an old one for a few reasons. Old felt must be removed in order to assess the condition of your roof decking, such as rotting wood or other structural issues. Also, if your roofer doesn't install a fresh layer of felt as is required by shingle manufacturers, your warranty may be voided. Finally, old underlayment removal is often included in the cost of roof repair or replacement, so there's no real benefit to leaving it on before installing a new layer.

The most crucial roof-strengthening method is achievable by following proper construction methods and guidelines from the start. To strengthen an existing roof, framers and DIYers can add hurricane ties or straps to the structure, sister rafters and other framing or truss members, or install additional fasteners or adhesives where necessary.

Hiring a reliable roofing contractor requires finding a company in your area with years of experience, holds the necessary licensing, and has a history of positive customer reviews and services. Start by researching whether a roofer you’re considering hiring holds the necessary certifications. Consider requesting customer references from your top contenders. Finally, get quotes from a few roofing companies and decide which provides the best value overall.

Rain shouldn’t come in through your ridge vents unless your vents are damaged or the rain is accompanied by very high winds. Most ridge vents use flashing or baffling to keep out rain, snow, and debris. If your ridge vent isn’t baffled, rain is more likely to enter your attic, so ridge vents with baffles are a better choice in areas with regular rainfall.

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