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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
Additional Photos
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
162 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
52 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

"Clear communication through the whole process. Questions were answered promptly and the roof looks amazing. I was extremely impressed with the work ethics of the crew, as well as the care the project manager and quality control team gave us."
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
81 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

102 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."
Logo
Work Photos
Work Photos
Work Photos
Work Photos

+5

4 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

"They are a little more expensive than other window installers but they did an amazing job. They installed all the windows in our home in a day, put all the window shades and furniture back in order, and cleaned everything up before they left. One of the screens had a cut on it and the installer fixed it immediately on site. Worth every penny. The person that did the estimate was very professional and not pushy. Great experience overall. The end result looks wonderful. A true pleasure to work with."
Asphalt Shingle Roofing
Asphalt Shingle Roofing
Recommended by85%of homeowners
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Showing 1-10 of 149
Roofing FAQs, answered by experts

Yes, clay and concrete tile roofs will keep your home cooler in the summer for two reasons. First, the material has low heat conductivity, so heat transfer from the sunlight and the outside air to your home will be very slow. Additionally, tile roofs have air gaps between the tiles and the roof decking, which helps further insulate your structure from heat gain. Light-colored tile is especially energy-efficient and will minimize how much outside heat transfers into your home.

You can damage your shingles if you use the wrong type of paint on them. You should always use acrylic latex paint specifically formulated for shingles. Other types of paint may trap moisture, which can cause bigger problems like rot and mildew. Considering that roof replacement costs $9,100 on average, it’s definitely best to avoid making this mistake.

Besides using the right paint, remember that painting your shingles will require increased maintenance.

Skipping the installation of a drip edge or gutter apron can lead to significant water damage. Without this component, water is more likely to seep under roofing materials or leak behind gutters, damaging the fascia, soffits, siding, and even the interior of your home, such as the attic. Over time, this moisture can cause rot, mold, and deterioration. In colder climates, a missing drip edge also increases the risk of ice dams, which can lead to expensive repairs. A drip edge is an essential part of a roof's drainage system, and some local building codes may even require its installation to protect the home from water damage.

During the framing process, builders connect the roof to the walls with materials, including metal connectors, plywood panels, and wood blocks. These roof-to-wall connections are important and provide weatherproofing, noise and temperature insulation, protection against pests, and home integrity. The type of connector and method used will vary, depending on your home’s construction and needs, and each has pros and cons in terms of cost, noise insulation, longevity, and reliability. Talk with your home or roofing contractor about the best connectors for your roof and walls, and what they recommend for your home.

A chimney liner is typically easier to install by pushing it down through the chimney with the help of a rope. Depending on your fireplace and the type of liner, installing it by pushing it up through the chimney could work, but operating from the top down is usually the best option.

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.