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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 S & G Roofing
S & G Roofing
4.8(
95
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair+10 more

Serving Cheshire, MA and surrounding areas

Approved

In business since 1998

Free estimates

Emergency services offered

"S&G Roofing did a phenomenal job! A++ work. I was impressed from the start with there quick response to my initial inquiry for an estimate, to the inspection and ease of understanding options available regarding product & payment choices. All employees who I spoke with and were involved with my house project conducted themselves in a professional manner and job was completed in a timely manner. They’re attention to detail with both installation of the two roofs as well as keeping area cleaned up and free of debris throughout was meticulous. I would highly recommend them if you are looking for a roofing company."
Additional Photos
Additional Photos
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Additional Photos
Additional Photos

+2

Response time2 days
3 neighbors recently requested a quote
Recommended by93%of homeowners
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 Cheshire, 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
155 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
54 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
75 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

78 neighbors recently requested a quote
Recommended by40%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

5 neighbors recently requested a quote
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 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 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
1702 neighbors recently requested a quote
Recommended by1%of homeowners
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Showing 1-10 of 149
Roofing FAQs, answered by experts

If the bay window extends beyond your existing roofline, you must add a roof or a small “skirt” to divert storm water and prevent water damage. The window roof can match your existing house roof, or be finished with copper or other decorative materials. Most bay windows have a roof with complete flashing regardless of their placement to prevent leaks into the home.

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 easiest type of roof to build is a shed-style or lean-to roof, which features a single sloping plane from one side of the building to the other. Unlike a gable roof with two sides meeting in the middle, a shed roof's single slope makes the construction process more straightforward. The rafters are typically single pieces of wood that span the distance, often without the need for additional supports.

There is a weight limit for walking on a roof, but it’s determined by your roof structure and not the roofing material, at least in the case of a metal roof. Consider that entire teams of roofers will be on top of your home during the installation, so the weight of a single person won’t compromise your roof. That isn’t the case for something like a tile roof, so a high weight limit is one benefit of a metal roof.

Spray foam roofs don’t stand up well to impact, so they won’t last as long as something like a tar and gravel roof and other flat roof materials in areas where extreme weather is common. Due to the reduced durability, you’ll also need more frequent maintenance and repairs for a spray foam roof, and those costs will add up over time. Spray foam roofs are relatively uncommon, so you may also struggle to hire a roofing contractor who can install one.

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.