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Top-Rated Asphalt shingle roofing installers and replacers in Cheshire - Updated Nov 2026

L&L Contracting LLC
4.6(
31
)
Asphalt Shingle Roofing - Install or Replace

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.
"
1 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for Modern Roofing, LLC
Modern Roofing, LLC
4.7(
89
)
Asphalt Shingle Roofing - Install or Replace

Serving Cheshire, CT and surrounding areas

Approved

In business since 2009

Free estimates

Warranties offered

"This company did impressive work! We needed to have our roof assessed for a recent problem with a leak. Starting from the estimate, they were the only company of many we interviewed that actually went on the roof. Their analysis was that while the roofing was of an age to be replaced, the problem was probably the result of some failing flashing and workmanship around our dormers, so their pricing estimate included that. Even with this work included they were very competitive. Working with the project coordinator Jay (who is also the individual who went on the roof and provided the estimate, and was onsite throughout the entire project! ), he kept us updated in a very timely fashion as to when the project could be scheduled. Once we had the day pinpointed, the crew showed up exactly at 7:00 AM and went to work, They carefully moved the furniture off the deck and protected any landscaping from the removal process. They worked the entire day (and then some) to make sure the house was waterproof. The finished the job the next day as we had to have some siding replaced on the dormers. The deck furniture was replaced, any trash or debris was nowhere to be found. Not a single roofing nail! We could not be happier with the entire experience with this company! I will be the first to recommend them to my neighbors and friends."
Response time1 day
Response rate100%
4 neighbors recently requested a quote
Avatar for Home Genius Exteriors
Home Genius Exteriors
4.9(
388
)
Asphalt Shingle Roofing - Install or Replace

Serving Cheshire, CT and surrounding areas

Approved

In business since 2004

Free estimates

Emergency services offered

Elevate your home with Home Genius Exteriors, setting the standard by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It?s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!

Asphalt Roofing
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing

+76

Recommended by96%of homeowners
Avatar for A1 Home Improvement, LLC
A1 Home Improvement, LLC
4.8(
19
)
Asphalt Shingle Roofing - Install or Replace

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."
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+3

Response time2 days
Response rate100%
12 neighbors recently requested a quote
Avatar for DiGiorgi Roofing & Siding Inc
DiGiorgi Roofing & Siding Inc
4.6(
202
)
Asphalt Shingle Roofing - Install or Replace

Serving Cheshire, CT and surrounding areas

Approved

In business since 1933

Free estimates

Emergency services offered

"John and Ryan skillfully fixed the subfloor under a leaking picture window without disturbing the sealed oak wood floor under the window. They did this by doing the repair in the basement under the leak and removed all wet wood and replaced it with new wood and new insulation. The next day, a DiGiorgi siding team came to replace all removed vinyl siding and install new insulation and new flashing around the picture window. Everything looks nice and neat and structurally sound."
Additional Photos
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+33

Response time3 days
Response rate100%
21 neighbors recently requested a quote
Avatar for Long Home
Long Home
4.3(
184
)
Asphalt Shingle Roofing - Install or Replace

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 Home Exteriors, LLC
Home Exteriors, LLC
4.9(
27
)
Asphalt Shingle Roofing - Install or Replace

Serving Cheshire, CT and surrounding areas

Approved (Corporate)

In business since 2015

Free estimates

Credit card accepted

"Home Exteriors Roofing did an excellent job on replacing my roof in just one day. From the quote process to the finished product, their team was very responsive and took care of questions in a timely manner. I found all members of their team very helpful and always willing to put the customer first. Would definitely recommend to family and friends."
Roofing
Roofing
Roofing
Roofing
Roofing

+132

Response time1 day
Response rate98%
7 neighbors recently requested a quote
Pattison Construction LLC
5.0(
10
)
Asphalt Shingle Roofing - Install or Replace

Serving Cheshire, CT and surrounding areas

Approved

In business since 1991

Free estimates

Emergency services offered

"Casey initially helped us with an ice dam winter 2025. He was the only contractor to respond to numerous calls we made and he did so promptly. He and his coworker resolved the problem and educated us about the issue going forward. It was such a positive experience that we invited him to quote a replacement roof on our 100 year old home. The bid was extremely fair; the work was completed efficiently and with all due care for our property and a beautiful end product. We would absolutely hire Casey and the Pattison team again!"
Additional Photos
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+1

Response time1 day
10 neighbors recently requested a quote
Recommended by80%of homeowners
Avatar for Home Genius Exteriors
Home Genius Exteriors
4.9(
399
)
Asphalt Shingle Roofing - Install or Replace

Serving Cheshire, CT and surrounding areas

Approved

In business since 2004

Free estimates

Emergency services offered

"Home Genius Exteriors provided my roof replacement January 29. From start to finish they executed a five star experience. They provided samples of available shingle roof options and colors, listed in detail quality roofing elements and provided a complete project manager plan (Thanks Jimmy Holm and AJ). The negotiations for price and value received makes this company stand out as a reputable, honest and provider of exceptional work. They are the real deal."
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing

+50

441 neighbors recently requested a quote
Recommended by94%of homeowners
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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.