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TRUSTED BY CHESHIRE, MA HOMEOWNERS

  • Average homeowner rating star icon4
    Average homeowner rating
  • Verified reviews icon230
    Verified roofing services reviews

Top-Rated Roofers in Cheshire - 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 BusinessAsphalt Shingle Roofing - Repair - For BusinessSealant for Roof - Apply- For Business+2 more

Serving Cheshire, 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
150 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 Cheshire, MA and surrounding areas

Approved

In business since 2004

Free estimates

Warranties offered

"Scott (the leader) Lewis and Davison did a stellar job on my 2 story home and garage. They go the extra mile! Have hired lots of folks who have done good work but this team I would give 10 stars to. Hope they are available again next fall!!! Very grateful."
Roof repair
Repairs
Roof maintenance.
New roof
Asphalt shingles, new roof.

+1

Response time10 hrs
60 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 Cheshire, 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
77 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 Cheshire, MA and surrounding areas

Approved (Corporate)

In business since 1979

Free estimates

Warranties offered

"Shawndel Evans and Greg Plaskett with Vault Roofing. They were great guys. They came to our house and explained our roof situation. The guys gave us a good deal and helped us get some financing so we could get the rest of the money for our loan. Would recommend Vault roofing!!!"
Stunning Curb Appeal
Stunning Curb Appeal
Stunning Curb Appeal
Stunning Curb Appeal
Stunning Curb Appeal

+5

55 neighbors recently requested a quote
Recommended by40%of homeowners
Avatar for Overstate Roofing Services Inc.
Overstate Roofing Services Inc.
4.2(
80
)
Asphalt Shingle Roofing - RepairFlat, Foam or Single Ply Roofing - RepairSealant for Roof - Apply+10 more

Serving Cheshire, MA and surrounding areas

Approved

In business since 2025

Free estimates

Emergency services offered

"I have to commend these guys and the job they did with my roof. I had a partially collapsed roof from the snow and ice buildup on my roof. I needed the repair done urgently and withing budget. I got may quotes on the job with some outrageous bidding to be honest. Overstate gave me a fair price and told me exactly what needed to be done. Within a week the job was completed and my home is leakproof again."
Roof replacement
Roof replacement
1731 neighbors recently requested a quote
Recommended by1%of homeowners
Avatar for ProEdge Remodeling - Roofing
ProEdge Remodeling - Roofing
4.3(
47
)
Asphalt Shingle Roofing - Install or Replace

Serving Cheshire, MA and surrounding areas

Approved

In business since 1961

Free estimates

Credit card accepted

"Install crew was perfect. No dust, no mess. Complete cleanup, and a perfect airtight install. For years we have had winter management strategies. Closing off room on the north side... and running space heater in those rooms during use. After installation of the ProEdge windows these rooms are as warm as the rest of the house. AMAZING! Recent warm days prove the advantage of triple glazed low-E windows, too. Nice and cool inside. I searched for years for new windows that met MY specifications . As a career engineer I am happy to recommend ProEdge to anyone. Their attention to detail is superb."
Asphalt Shingle Roofing
Asphalt Shingle Roofing
Recommended by85%of homeowners
Avatar for JAF Contracting
JAF Contracting
5.0(
8
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For Business+22 more

Serving Cheshire, MA and surrounding areas

Approved

In business since 2010

Free estimates

Emergency services offered

"Jake was super responsive and was the only contractor who was timely and courteous with his communication. His crew did great work repairing my roof in one day. He was clear and fair with his estimate so there were no unexpected costs when payment was due. I highly recommend Jake and his team."
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Work Photos
Work Photos
Work Photos
Work Photos

+5

7 neighbors recently requested a quote
...
Showing 1-10 of 149
Roofing FAQs, answered by experts

Whether a metal or shingle roof is better for you depends on your preferences. Standing seam metal roofs require little to no maintenance, but if you install a screw-down metal roof where the fasteners are exposed, the gaskets on the fasteners will dry rot and need to be replaced. Generally, screw-down metal roofs need to be re-screwed every 15 to 20 years.

Metal roofs are energy-efficient and have extended warranties, while asphalt shingles are less durable than most. They tend to lose color and get damaged over time, and absorb heat from the sun.

Re-roofing is the process of placing a layer of shingles over top of existing shingles, rather than pulling out those shingles and replacing them. Compared to a full roof replacement, re-roofing typically costs less and requires less labor and time. It's not an option for everyone, though. You may need a full roof replacement if your roof already has more than one layer of shingles. A full replacement may also be necessary if your roof has extensive damage.

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.

Yes, a new roof will add value to your home, often providing a return on investment (ROI) of between 60% and 70%. Not only will a new roof boost curb appeal, but savvy homebuyers will also know that a new roof means they won’t have to worry about roof leaks and related damage for years after closing. They’ll also know that they’ll save money by potentially having decades before they need to worry about paying for repairs or replacement.

The best material to sheath a roof will depend on your budget and if you require the strength of more robust materials. For most homes, the added strength is unnecessary, and oriented strand board, or OSB, makes sense. It’s inexpensive and robust enough for most roof types. Another popular but slightly more expensive option is plywood.

The Cheshire, MA homeowners’ guide to roofing services

From average costs to expert advice, get all the answers you need to get your job done.