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

Yes, removing a chimney is a difficult and major undertaking. Chimneys often provide structural support to a home, so if it's a load-bearing structure, you'll need to take extra precautions to maintain your home's integrity. A project of this complexity typically requires a structural engineer, a masonry contractor, and a demolition crew. The removal process may involve taking the chimney out brick by brick from inside the walls. The cost for chimney removal can range from $2,000 to $10,000, depending on the job's complexity. Due to the difficulty and cost, some homeowners opt to remove the fireplace and seal the chimney at the top and bottom, sometimes also removing the visible exterior portion at the roofline.

Yes, because it prevents water damage, deters pests from accessing the roof decking, protects the roof from wind damage, and lengthens the roof's life. Plus, building codes require it. 

Due to the complexity and weight of tiles, DIY is not recommended. Professional installation ensures proper alignment and durability.

If you live on the West Coast or anywhere with the threat of wildfires, you likely want to take steps to fireproof your home. Besides waterproofing and life span, rubber roofing also is noted for being fire resistant. Consult a professional roofer for details on what type of roofing would be best for you if fire resistance is a priority.

Winter is the least expensive time of year to replace a roof due to decreased demand. However, it’s not an ideal time to replace your roof, as there are numerous factors that can inhibit the work, including shorter days, snow and ice, and cold temperatures.

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