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

Avatar for On Top Roofing
On Top Roofing
4.6(
179
)
Asphalt Shingle Roofing - Install or Replace

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 2004

Free estimates

Emergency services offered

"On Top Roofing is Top of the Line Roofer. Professional delivery with solid quality! Company was hired to correct the issues caused by a prior roofer whose incompetence has cost me additional thousands in repair. On Top Roofing installed a ridge vent that the prior roofer only placed on the roof, re-flashed the chimney where prior roofer failed to install to match new rook lines, re-surface flat rook where prior roofer ignored. In addition, On Top Roofing was used on apartment buildings to help close up the roof and eliminate a bat problem. On the Top Roofing is the only roofing company to use. It takes a while to get on their schedule, but they show when they say the will and do the job they say they will do. Only hire On the Top!! You will not regret."
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+11

Response time11 hrs
Response rate100%
4 neighbors recently requested a quote
Avatar for Mighty Dog Roofing MetroWest Boston
Mighty Dog Roofing MetroWest Boston
5.0(
35
)
Asphalt Shingle Roofing - Install or Replace

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 2021

Free estimates

Emergency services offered

"Shortly after leaving a message for a return call from Mighty Dog, (having discovered a significant leak into our office), Anthony appeared at our house!! It was such a relief to have a roofing expert show up as the water was pouring into our house!! So he and Mighty Dog get an A+ for prompt reply!!! Anthony was extremely personable, very pleasant to work with and immediately installed a large tarp over our flat roof to stop the water leakage. When the weather warmed up enough to begin the repair, he and his crew did a great job replacing our skylight and flat roof and the clean up job was impeccable which we really appreciated. I would give him and Mighty Dog an A+ for customer service and quality of work!!!! It could not have been a better experience (if one has to have a major roof leak!)"
Asphalt Shingle Roof
Wood Shake Roof
Slate Roof
Metal Roof
Slate Roof

+14

4 neighbors recently requested a quote
Recommended by78%of homeowners
Avatar for Willard Co
Willard Co
4.6(
164
)
Asphalt Shingle Roofing - Install or Replace

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 1873

Free estimates

Emergency services offered

"Everything was great except cleanup. There was a misunderstanding about which shingles we wanted, but Willard made good on it. They even removed a small area where they had installed the wrong shingles and replaced them with the right shingles, all at no extra charge. The new roof looks great. The only problem was cleanup. We found a large number of nails in our yard and on our driveway, and a lot of pieces of plastic lying around."
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+13

Response rate100%
20 neighbors recently requested a quote
Recommended by95%of homeowners
Avatar for Ranch Roofing
Ranch Roofing
4.7(
693
)
Asphalt Shingle Roofing - Install or Replace

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 1996

Free estimates

Warranties offered

"I recently had Ranch Roofing install a new roof on my home and I am so grateful I chose them! I honestly cannot say enough good things about this company. From the very beginning, when I was searching for a roofing company, choosing a shingle color, and asking questions (since I know very little about roofing), the entire experience was wonderful. They were patient, knowledgeable, and always took the time to answer my questions and make sure I understood everything. The process was easy and stress-free. On installation day, the crew arrived, put up the tarps, and got right to work. The old roof came off, the new roof went on, and the results are absolutely beautiful! I chose Onyx Black, and I am so glad I did. It looks sharp! The new intake vents and ridge vents were also installed, and everything looks amazing. I had read about their reputation and how they stand behind their work, which gave me confidence in choosing them. They certainly lived up to that reputation. They are wonderf"
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+2

Response time10 hrs
Recommended by97%of homeowners
Avatar for RB FARINA ROOFING & CONSTRUCTION, INC.
RB FARINA ROOFING & CONSTRUCTION, INC.
4.2(
80
)
Asphalt Shingle Roofing - Install or Replace

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 1984

Free estimates

Emergency services offered

"Very well. They ran out of roofing shingles toward the end of the job, and we had to wait two days for the last finishing touches. Otherwise all was well, and they cleaned up after themselves. Very quick."
commercial TV RB Farina Roofing Co
commercial TV RB Farina Roofing Co
commercial TV RB Farina Roofing Co
commercial TV RB Farina Roofing Co
commercial TV RB Farina Roofing Co

+32

31 neighbors recently requested a quote
Recommended by84%of homeowners
Roofer's Edge & Siding Inc
4.5(
66
)
Asphalt Shingle Roofing - Install or Replace

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 2006

Free estimates

Emergency services offered

"They were able to do the job three weeks earlier than scheduled. The workers showed up right on time, went right to work and got the job done in one day as promised at the exact price quoted. All of the debris was cleaned up and the yard was left in the same condition as when they arrived. The workers were professional and the roof looks awesome. I would highly recommend Roofers Edge to anyone looking to replace their old roof.
"
Response time8 hrs
1 neighbors recently requested a quote
Recommended by91%of homeowners
Avatar for Newton Roofing Residential
Newton Roofing Residential
4.3(
191
)
Asphalt Shingle Roofing - Install or Replace

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 1989

Free estimates

Emergency services offered

"I highly recommend Newton Roofing Residential. In 2014, they replaced the entire roof on my home with high quality materials, in a safe and timely manner, and at a very competitive price. In 2020, I decided to address another need - my aging second floor porch, which serves as a roof to the first floor porch below. It was becoming increasingly unsafe due to wood rot, with a soft floor and loose railings. Given my positive customer experience in 2014, calling Newton Roofing in 2020 was an easy decision - I did not get quotes from any other company. Rich came out and provided a detailed explanation of the materials and labor needed to replace the porch and to install new railings that best match the style of my home, and he followed up with a very competitive quote for the project. Gus and Julio were the on-site team who completed the project and their work was exceptional. Both men were incredibly skilled and meticulous, and thoroughly impressed me with their attention to detail at every point in the project. They worked on my home as if it were their own, which I greatly appreciated. I was so pleased with their knowledgeable and experienced craftsmanship. As you can see, I am a very satisfied Newton Roofing Residential customer!"
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+26

Response time1 day
Recommended by89%of homeowners
Avatar for Karales Home Improvement
Karales Home Improvement
4.7(
95
)
Asphalt Shingle Roofing - Install or Replace

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 1981

Free estimates

Emergency services offered

"We hired Mike for a gutter job after finding him though Home Advisor and were very happy with the work and his price. He informed us we needed to have our roof replaced. He left us an estimate to remove the current shingles and replace them with new ones. We got 2 more estimates for the work but Mike's price was the best. They did a great job and cleaned up before they left. We are very happy with his work and the professional crew he has working for him!"
Vinyl siding after
Victorian Remodel
SIDING
SIDING
SIDING

+8

Response time5 hrs
3 neighbors recently requested a quote
Recommended by67%of homeowners
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FAQs for asphalt shingle roofing installation and replacement projects in Chestnut Hill, MA

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 Chestnut Hill, MA 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.