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TRUSTED BY CHESTER, MA HOMEOWNERS

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

Top-Rated Roofers in Chester - 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 BusinessSealant for Roof - Apply- For BusinessAsphalt Shingle Roofing - Repair - 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 !"
Roof Replacement
Roof Underlayment
Roof Installation
Roof Prep & Install
Shingle Installation

+1

Response time3 days
162 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 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
52 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 Chester, 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
76 neighbors recently requested a quote
Recommended by92%of homeowners
Avatar for Vault Roofing
Vault Roofing
4.4(
35
)
Asphalt Shingle Roofing - Install or Replace

Serving Chester, MA and surrounding areas

Approved (Corporate)

In business since 1979

Free estimates

Warranties offered

"The work was done exactly as expected. Tom Schmidt,the representative, was personable and trustworthy. I will recommend him to any of my friends or neighbors if they want roofing advice."
Stunning Curb Appeal
Stunning Curb Appeal
Stunning Curb Appeal
Stunning Curb Appeal
Stunning Curb Appeal

+5

101 neighbors recently requested a quote
Recommended by40%of homeowners
Avatar for Overstate Roofing Services Inc.
Overstate Roofing Services Inc.
4.2(
79
)
Asphalt Shingle Roofing - RepairFlat, Foam or Single Ply Roofing - RepairSealant for Roof - Apply+10 more

Serving Chester, MA and surrounding areas

Approved

In business since 2025

Free estimates

Emergency services offered

"5 Stars ! I hired Overstate multiple times . Yani was so polite and professional , I needed to replace my plaster ceilling in 4 different rooms . It started in a small project and slowly I decided working with Yani on a new bathroom remodel , framing and other drywall services . I know that overstate does roofing as well , I?ll definitely consider them when I replace my new roof ."
Roof replacement
Roof replacement
1836 neighbors recently requested a quote
Recommended by1%of homeowners
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

"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%
15 neighbors recently requested a quote
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Roofing FAQs, answered by experts

Generally, the term “rolled roofing” refers to MSR (mineral surface roll) roofing. This type of roofing is similar to asphalt shingles but comes in a roll that’s unraveled and installed over your roof deck. There are many types of rolled roofing, including TPO, EPDM, and modified bitumen roofing (aka torch down roofing).

The four types of roof sheathing are plywood, oriented strand board (OSB), planks, and tone-and-groove boards. The overwhelming majority of homes use the first two (especially OSB) and the other two are not often seen outside of special use cases. Methods of sheathing include solid sheathing, open sheathing where there are gaps, and plank sheathing. Most roofs are solid sheathing.

A cool roof can be worth it in the right climate. Cool roofs are excellent at reflecting solar heat away from your home, so if you live in a warm or hot climate, they can be a great roofing choice. Some cool roofing materials are even eligible for tax credits. However, they cost more than traditional roofing and don’t retain heat as well as traditional roofing, so they’re not ideal if you live in a cold climate.

The most important thing to remember when laying shingles is to work from the bottom of the slope to the top. This leaves you with a top overlap that directs runoff from one row to the next until it reaches the eave for disposal. You should also make sure you follow the manufacturer's instructions and the local building code for nailing patterns and frequency so all of your hard work stays put through varying weather conditions.

When installed and maintained properly, a cedar shake roof should last up to 60 years. Severe weather and high winds will damage your roof, reducing its life span. Expect a shorter life span if the roofer didn't use top-grade material, didn’t have cedar shake expertise, didn’t create the proper ventilation, or didn’t use the correct fasteners. Keeping up with maintenance will help it last longer. It’s also a good idea to get roof inspections on a regular basis to help spot repairs before they become major issues.

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.