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    Average homeowner rating
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    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 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

"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
153 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

"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
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

"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
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

75 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
1700 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."
Logo
Work Photos
Work Photos
Work Photos
Work Photos

+5

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

Venting a gas water heater out of the roof is preferable in most cases. Heated exhaust gases naturally rise, so a vertical vent pipe is efficient. If you’re trying to vent through a pipe exiting a wall, the angle of the pipe may be more horizontal than vertical, making the venting system less effective. If you go through a wall, you may need to add a fan to ensure a successful expulsion of the gases outdoors.

If you're looking for a dependable and affordable option for garage roofing, asphalt shingles offer a durable way to blend a detached garage in with the surrounding residential aesthetic. If you're looking for a more durable and protective option because you're storing expensive equipment in your garage, consider metal roofs that perform well against snow, ice, hail, and heavy rains.

The proper specifications for furring strips can vary, so you should always consult the roofing manufacturer's guidelines or your roofer. However, general recommendations are as follows:

  • Thickness: Furring strips are typically 1 to 1-1/2 inches thick, meaning standard 1-by or 2-by lumber works well. In areas with extreme winds, a thinner strip may be preferred to limit how much air can get under the roof and cause uplift. A thicker strip can add slightly more insulation but will also increase installation costs.

  • Spacing: The recommended spacing for furring strips is between 12 and 24 inches apart on center. Proper spacing is crucial for ensuring good airflow, adequate drainage, noise reduction, and better energy efficiency. The ideal spacing can depend on the roof's pitch and the specific type of metal roofing being installed.

Metal roofs last for between 50 and 70 years, and asphalt roofs last for between 20 and 25 years, with some lasting as long as 30 years. In most cases, you’ll get double the life or more out of a metal roof than you would from a shingle roof, which helps make the higher cost of a metal roof more manageable.

A new roof may improve insulation and ventilation problems that can lead to ice dams, but it’s not a solution for preventing them. All roofs are susceptible to the conditions that cause ice dams, so it’s best to invest your money into insulation and gutter management solutions rather than a new roof if you don’t need a replacement yet.

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.