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
)

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!"
Roof Replacement
Roof Underlayment
Roof Installation
Roof Prep & Install
Shingle Installation

+1

Response time3 days
164 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
)

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."
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
)

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
55 neighbors recently requested a quote
Recommended by92%of homeowners
Request Quote
Avatar for Power Home Remodeling
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."
GAF Fortitude Roof
GAF Fortitude Roof
GAF Fortitude Roof
GAF Fortitude Roof
GAF Fortitude Roof

+20

3410 neighbors recently requested a quote
Recommended by84%of homeowners
Request Quote
Avatar for ProEdge Remodeling - Roofing
ProEdge Remodeling - Roofing
4.3(
47
)

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
)

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
)

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%
49 neighbors recently requested a quote
Request Quote
Avatar for Advanced Seamless Gutters
Advanced Seamless Gutters
4.4(
210
)

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
66 neighbors recently requested a quote
Recommended by92%of homeowners
Request Quote
...
Showing 1-10 of 191
Roofing questions, answered by experts

Complete house winterization goes above and beyond the list we created above. In addition to everything listed, full house winterization also includes:

  • Performing a home energy audit.

  • Preparing your deck and patio for winter.

  • Learning how to start a snowblower.

  • Replacing smoke detector batteries.

  • Installing outlet gaskets.

  • Installing storm doors.  

Many insurance policies will not cover a roof with two layers of shingles. An additional layer of shingles increases the risk of various kinds of damage, and insurers typically won’t pay claims on a roof with an overlay. Adding a layer of shingles may even jeopardize your insurance coverage entirely, so check your policy to ensure you stay within coverage guidelines. 

No, a metal roof will not make your house hot. In fact, metal roofs help keep your home cooler by reflecting heat instead of absorbing and transmitting it inside. Metal also has high thermal conductivity, which means it gains and loses heat quickly. While the sun may heat the metal, the roof rapidly transfers that heat back into the air rather than retaining it. This reflective property can lead to energy cost savings of up to 40%, as your cooling system won't need to work as hard to maintain a consistent indoor temperature.

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.

As with any roofing material, there are benefits and drawbacks to consider before installing roll roofing. On the plus side, roll roofing is budget-friendly, lightweight, and comparatively easy to install. It is also ideal for low-sloped roofs and lasts around 10 years. The cons of roll roofing, however, include its low durability compared to roofing materials, restricted color choices, and low ROI.

Pros:

  • Low-cost

  • Lightweight

  • Cut to size

  • Easy and quick installation 

  • Designed for low-sloped roofs

  • Waterproofs your roof for an average of 10 years

  • Easy to purchase and transport

Cons:

  • Less durable than asphalt shingles

  • More prone to cracks and tears

  • Short life span

  • Not as many color or style choices

  • Not as aesthetically pleasing as shingles, wood, or clay tiles

  • Not preferred for a higher home resale value

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