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  • 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
152 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

69 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
1704 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

6 neighbors recently requested a quote
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Showing 1-10 of 150
Roofing FAQs, answered by experts

Clay tile roofing is common for traditional villas, while flat roofs are more standard for modern villa homes. Clay tile roofs are long-lasting, require little maintenance, and are great for warmer climates. Flat roofs are usually low-cost, energy-efficient, and allow for rooftop gardens. 

Clay tile roofing is more susceptible to damage from impact than something like a metal roof or even asphalt shingles, so they aren’t ideal in areas that see frequent windblown debris or hail. Clay tile roofs are also an average of $8,000 more expensive than asphalt shingle roofs, so up-front cost is an important consideration to make before committing.

Though cedar shakes often get confused with shingles, there are a few key differences between wood shakes and wood shingles. For one, cedar shingle prices are lower, although shingles are less durable than wood shakes. Cedar shakes are thicker than shingles (shingles range from about 3/8 to 1/2 inches thick, compared to 1/2 to 3/4 inches thick for shakes). Wood shakes are handmade, while shingles are usually machine-made. Also, wood shakes work better on steeper roofs than shingles do. While the cost of cedar shingles is more budget-friendly, there are many great reasons to choose shakes.

Yes, shingles should overhang the drip edge, typically between 1/2-inch and 3/4-inch. An overhang shorter than 1/2-inch can allow wind-driven rain to get under the shingles and damage the roof deck or fascia. Conversely, an overhang longer than 3/4-inch increases the risk of shingles getting caught by strong winds, which can lead to roof uplift. Always check your local building code for exact overhang requirements in your area.

Costs depend on material, labor, and additional features like underlayment or insulation.

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.