Top-rated asphalt shingle roofing installers and replacers.

Get matched with top asphalt shingle roofing installers and replacers in Cheshire, CT

Enter your zip and get matched with up to 3 pros

Matching on HomeAdvisor

Share some details icon
Share some details about your home project.
Match with local pros icon
Within moments, match with highly-rated local pros.
Compare quotes icon
Compare quotes and choose the best pro for the job.

Find Asphalt shingle roofing installers and replacers in Cheshire

Avatar for Best Way Siding and Roofing, LLC
Best Way Siding and Roofing, LLC
4.8(
179
)

Serving Cheshire, CT and surrounding areas

Approved

In business since 2012

Free estimates

Emergency services offered

"Best Way Siding and Roofing was the first to contact me when I signed up on HomeAdvisor and the first to give me an estimate. Luis was knowledgeable and competent. He arrived with the most impressive presentation (handouts) of all the contractors who came to give us estimates. The first thing I liked about Luis was that had a copy of his certificate of liability insurance and registration with the Dept of Consumer Protection (which I confirmed as I had worked with a construction management company before), This gave Luis a very good first impression. Luis was knowledgeable and answered our questions and addressed our concerns. He was not pushy. We told him upfront that we were getting multiple quotes, and he was the first. After seeing other roofing contractors we went with Best Way Siding and Roofing. I did not like the big companies, the franchises; not my style. I like the small family company, so we went with him, and we are glad we did. Best Way Siding and Roofing removed our old roofing shingles and replaced multiple pieces of rotted plywood before installing a well-known roofing system and replacing our skylight. The job was done in a day. The crew kept my husband informed of their progress and took pictures of the rotted plywood and showed him the pieces. They did a wonderful job. I usually second guess myself when making any decisions but not this time. I have already recommended Best Way Siding and Roofing to others."
Roof Replacement/ Flat Roof
Roof Replacement
Guest Room
Garage/Barn Shed Roof Replacemnt
Charcoal GAF

+66

Response time9 hrs
Response rate98%
39 neighbors recently requested a quote
L&L Contracting LLC
4.6(
31
)

Serving Cheshire, CT and surrounding areas

Approved

In business since 1987

Free estimates

Customers say: Super punctual

"L&L made several visit including Saturday and Sunday to evaluate the job and made several suggestions as to the best way to replace the roof without any damage to the interior of our house.They promised to pick a good day to do the job and complete the job in one day. They arrived at about 7:30 AM with a crew of about 10 workers and had the complete roof replaced and the yard completely cleaned up before 4:30 PM. This included new lead flashing for the chimney and replacing 2 sheets of plywood. In addition they guaranteed the workmanship of the roof for as long as we owned the house. We had no problems at all.
"
Recommended by100%of homeowners
Avatar for Modern Roofing, LLC
Modern Roofing, LLC
4.7(
89
)

Serving Cheshire, CT and surrounding areas

Approved

In business since 2009

Free estimates

Warranties offered

"I would like to give a big shout out to Jay, who provided us with a quote to replace our roof. He did a great job communicating with us throughout the entire project. His team did an outstanding job replacing our roof. They protected our landscaping and did a thorough clean up after roof installation was complete. The team arrived promptly in the morning and worked tirelessly that day until the job was complete. They were professional and friendly. I would highly recommend Modern Roofing. They have a great value for the money."
Response time1 day
Response rate100%
4 neighbors recently requested a quote
Avatar for DiGiorgi Roofing & Siding Inc
DiGiorgi Roofing & Siding Inc
4.6(
202
)

Serving Cheshire, CT and surrounding areas

Approved

In business since 1933

Free estimates

Emergency services offered

"DiGiorgi came when they said they would, and replaced the roof, despite the extra work of dealing with the slate, in a day and a half. There was a small problem with a down spout. They came promptly after I called, and came up with a creative solution to fix it. Throughout, they were pleasant and professional."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+33

Response time3 days
Response rate100%
17 neighbors recently requested a quote
Avatar for Long Home
Long Home
4.3(
184
)

Serving Cheshire, CT and surrounding areas

Approved

In business since 1999

Free estimates

Emergency services offered

"The install team arrived on time and were very professional, polite and worked very well as a team. The roof shingle installation was completed with expert crafthmanship and I am very pleased with the final result!!!"
Recommended by87%of homeowners
Avatar for A1 Home Improvement, LLC
A1 Home Improvement, LLC
4.7(
13
)

Serving Cheshire, CT and surrounding areas

Approved (Corporate)

In business since 1980

Free estimates

Emergency services offered

"A1 did a great job on my new roof and gutters. Clearly defined scope of work, prompt and flexible scheduling, used high-quality shingles with a good warranty. They don't subcontract out their roofing work, which is a big plus. Considerate workers, documented the new roof with photos and videos, and had everything cleaned up by the end of the day. Recommended for a trouble-free roof replacement."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+3

Response time2 days
Response rate100%
12 neighbors recently requested a quote
Avatar for Home Genius Exteriors
Home Genius Exteriors
4.9(
387
)

Serving Cheshire, CT and surrounding areas

Approved

In business since 2004

Free estimates

Emergency services offered

"The young man that came to see my missing shingles on my roof, was professional, informed, and polite. The only issue was that the company does NOT conduct repair as I needed. The company only replaces the entire roof. I am glad he came and advised about replacing the roof if we decide to do that and decide that we can afford it. Right now I need to repair the missing shingles. and he/ his company can not help me."
344 neighbors recently requested a quote
Recommended by96%of homeowners
Avatar for Roof Smart Home Improvement & Construction
Roof Smart Home Improvement & Construction
5.0(
19
)

Serving Cheshire, CT and surrounding areas

Approved

In business since 2024

Free estimates

Credit card accepted

"Marco and Roof Smart did an amazing job on our fascia, soffits, and gutters. The quality of the work completely transformed the look of our home. We had a hard time finding a trustworthy contractor who offered fair pricing and would actually deliver the vision we wanted, but Marco exceeded our expectations. Professional, reliable, and detail-oriented from start to finish. Thank you, Marco! We will definitely be using Roof Smart again for future projects."
New roof
New roof
New roof
New roof
11 neighbors recently requested a quote
...
Showing 1-10 of 413
FAQs for asphalt shingle roofing installation and replacement projects in Cheshire, CT

Roofing professionals can usually install a medium-sized asphalt shingle roof in two to three days. Installation time increases if your roof is particularly steep or difficult to access or has features like chimneys or skylights that roofers must work around.

Three-tab asphalt shingles usually have the lowest upfront cost of any roofing shingle material. They’re sturdy and typically last 15 to 20 years. However, they may have a shorter lifespan in especially hot or cold climates. Talk to a local roofing professional about the best materials for your climate. In some cases, materials with a higher upfront cost may save you more on repairs or replacements in the long run.

Start by multiplying the length by the width of your roof to calculate the square footage. Most shingle replacement costs $4 to $12 per square foot for materials and labor, depending on factors like the material and the slope of your roof. Once you know the size of your roof, you can calculate a rough estimate of total costs or contact a local roofing professional to provide you with a custom quote.

Asphalt shingles are generally considered to be a low-maintenance item. However, cleaning your asphalt roofing can help prolong the lifespan and keep it looking fresh. If you’re comfortable with DIY and have the proper equipment, you may be able to clean your asphalt shingles yourself. However, if you have an especially high or steep roof, it’s usually safer to hire a professional roof cleaner.

The Cheshire, CT homeowners’ guide to asphalt shingle roofing installations and replacements

From average costs to expert advice, get all the answers you need to get your job done.