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

Verified Reviews for Roofing pros in Cheshire, MA

*The Angi rating for Roofing companies in Cheshire, 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 Cheshire, 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 27, 2026

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

"They did a very good service, fast and very well done I did contacted them a week later and they came right over to fixed the roof and also the window leaking."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+2

Response time2 days
3 neighbors recently requested a quote
Recommended by93%of homeowners
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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
155 neighbors recently requested a quote
Recommended by97%of homeowners
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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
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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
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Avatar for JP Carroll Roofing - Western Mass
JP Carroll Roofing - Western Mass
5.0(
10
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairInspection - Roofing

Serving Cheshire, MA and surrounding areas

Approved

Super Service Award Winner

In business since 1988

Free estimates

Warranties offered

"Excellent job. Courteous professionals. Good communications. On time, on budget, good job policing the grounds, both mine and the neighbor's."
JP Carroll Roofing
JP Carroll Roofing
JP Carroll Roofing
JP Carroll Roofing
JP Carroll Roofing

+13

71 neighbors recently requested a quote
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Avatar for Long Home
Long Home
4.3(
184
)
Asphalt Shingle Roofing - Install or Replace

Serving Cheshire, MA and surrounding areas

Approved

In business since 1999

Free estimates

Emergency services offered

"Our company contact Aaron was patient, professional and took the time to educate us about roof components and their installation."
Recommended by87%of homeowners
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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
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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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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
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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

Whether you should choose a flat roof or a sloped roof depends on your particular situation. Flat roofs tend to be less expensive to install. However, sloped roofs have longer lifespans and stand up better to heavy snow and other inclement weather.

Keep in mind that even a flat roof needs to have a slight slope, usually around 1/2 inch for every foot. If it is completely flat, water will pool and cause damage, either from weight or leakage or rot.

Depending on the type of damage your roof shingles have, you may be able to simply repair them without having to replace them. However, if there are more than a few to repair, replacement is likely the easier option. You may only need to replace a few of them. Repair shingles by applying roofing sealant directly under the shingle's damage and then directly over it. 

Roof vents are an essential part of a roof, as they promote energy efficiency by keeping warm, humid air at bay. The roofing material, especially asphalt shingles, will not last as long as it should (about half of its manufacture life) if the attic is not ventilated. Also, going without ventilation means having a warm attic that demands more from your air conditioning system (and your wallet, once the bills come). Ridge vents and roof vents also prevent a host of other icky moisture-related problems like rot, mold, and mildew.

If you need to replace the roof over your attached garage, a roofing contractor can perform what is called a partial roof replacement that only affects garage roofing. However, it's important to keep in mind that only replacing a portion of your roof creates a situation where your roofing has two different lifespans. You will also miss out on the opportunity for a full roof warranty. In some cases, having two different roofs on your home could increase risks for leaks. When replacing the roof on a detached garage, homeowners have the option to make the project bigger by upgrading their home roof alongside their garage roof. However, this isn't necessary if your home has a newer, properly functioning roof. It is better to try to match the new garage roof to your home's existing roof instead.

The best way to check if a roofing company is legit is by asking the roofer for their license number. They should have no issue providing you with this information if they’re legitimate. You can also look to see if they have an online presence, read reviews, and ask contractors you’ve worked with before if they know the roofing company.

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.

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