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TRUSTED BY CHESTNUT HILL, MA HOMEOWNERS

  • Average homeowner rating star icon4.4
    Average homeowner rating
  • Verified reviews icon2k+
    Verified roofing services reviews

Top-Rated Roofers in Chestnut Hill - Updated Nov 2026

Avatar for Ranch Roofing
Ranch Roofing
4.7(
692
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessFlat, Foam, or Single Ply Roofing - Install or Replace+7 more

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 1996

Free estimates

Warranties offered

"We are very pleased with the result. The job was done in a day by a large team, who wrapped up the house (!), stripped off the old roofing, and put in the new skylights and roof within the day. There were some delays due to poor (wet) weather, but we can't really blame Ranch Roofing for that."
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+2

Response time10 hrs
Recommended by98%of homeowners
Avatar for On Top Roofing
On Top Roofing
4.6(
179
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Install or Replace - For Business+26 more

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 2004

Free estimates

Emergency services offered

"We had a great experience with On Top Roofing. They returned my call for a quote request within one day and had someone out to give an estimate within a couple of days after that. We obtained several estimates, On Top was the only company that actually climbed up on a ladder to really look at the area of concern and where work needed to be done during the estimate. After we received the quote, the work was done within the scheduled time and completed as agreed. I would definitely consider On Top again for future roofing needs."
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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

"Excellent communication by owner Anthony. Truly appreciated the drone view shots before, during and after our roof project. Professional, punctual and awesome crew! We had our skylights replaced and architectural Owens Corning shingles placed.. Quality of work, protection of our plantings and property was outstanding. All completed in a day not to mention Anthony helped replace a few rotted boards on our deck. Overall would highly recommend Mighty Dog Roofing."
Asphalt Shingle Roof
Wood Shake Roof
Slate Roof
Metal Roof
Slate Roof

+14

3 neighbors recently requested a quote
Recommended by78%of homeowners
Avatar for Doherty Slate Roofing
Doherty Slate Roofing
4.8(
71
)
Metal Roofing - Install or ReplaceWood Shake or Composite Roofing - RepairInspection - Roofing+14 more

Serving Chestnut Hill, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2000

Free estimates

Emergency services offered

"I am so thrilled to have found Doherty Slate Roofing! From scheduling the visit to get an estimate, which was very reasonable, to scheduling to have the work done...Liz, in the office, was incredibly efficient. And a VERY BIG THANK YOU to Jason, who was on the job within a week and who did an amazing job repairing several broken slate tiles on our roof. Thank you Jason and Liz for everything!!"
Slate roofing newton
Roofing Rubber roofing Boston
Slate roofing Boston
Slate roofing Jamaica Plain
Slate roofing contract Boston

+125

Response time6 days
2 neighbors recently requested a quote
Recommended by80%of homeowners
Avatar for Newton Roofing Residential
Newton Roofing Residential
4.3(
191
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair+26 more

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 1989

Free estimates

Emergency services offered

"Newton Roofing responded quickly to my general roof repair request. Rich Mello came out and assessed the situation and suggested both a roof patch repair and/or a partial roof replacement. He was informative and helpful. Not a hard sell at all. Quickly emailed an estimate for both jobs. I thought the price was good on both. I went with the patch repair and a month later it was completed. They even were good at cleaning up and looking for dropped nails."
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+26

Response time1 day
Recommended by89%of homeowners
Avatar for RB FARINA ROOFING & CONSTRUCTION, INC.
RB FARINA ROOFING & CONSTRUCTION, INC.
4.2(
80
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Install or ReplaceFlat, Foam or Single Ply Roofing - Repair+19 more

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 1984

Free estimates

Emergency services offered

"The contractor was knowledgeable and skilled and took the time (perhaps 15 minutes) to examine 4 or our 6 roofs (we have little house with two main sloped roofs, one small less sloped roof and three small flat roofs).
He did not take the time to examine the remaining roofs, saying that he had done enough for us, that there was no charge and that we were in good shape. While I believe the contractor and am somewhat reassured, I would have preferred that he take another few minutes to examine the remaining roof or even to say that he would do that for a charge.
The reason I feel this way is that each roof is different. Flat roofs last 20 years. Ours are 17 years old. One of the flat roofs not inspected is different in that it has glue seams in the middle that may or may not be a problem. It was such a bad winter last year, and I had noticed that one of our flat roofs was starting to curl up a little bit where it is attached under a gutter (hard to explain). I also had noticed a stain that was due to an ice dam (although we had no leakage inside). So concern for our roofs is warranted
As it is, I will be getting another roofer to come to inspect at least the last flat roof and for a second opinion. This certainly is not the end of the world. I might or might not have opted to have the second inspection if the contractor had examined the remaining flat roof

"
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

46 neighbors recently requested a quote
Recommended by84%of homeowners
Avatar for Stella Roofing Services
Stella Roofing Services
5.0(
14
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair+5 more

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 2008

Free estimates

Emergency services offered

"FANTASTIC COMPANY. DIAGNOSED THE PROBLEM BETTER THEN THE OTHER 2 COMPANIES I CALLED. STEVE WAS VERY KNOWLEDGABLE AND TOOK THE TIME TO EXPLAIN AND SHOW ME WHAT MY ISSUE WAS. CLEANED UP AFTER THE JOB AND SENT PICTURES AS THE WORK WAS BEING COMPLETED. THIS COMPANY IS NOW MY NUMBER ONE GO TO ROOFING COMPANY"
New side walls and siding
No job is too small,
For those tight to get to areas in Boston and the surrounding cities we have our own roll off dump trucks, trash chute and staging.
Re roof with 6 new Velux solar skylights
Installing a new construction Velux Skylight

+29

Recommended by7%of homeowners
Avatar for Long Home
Long Home
4.3(
96
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or Replace

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 1945

Free estimates

Emergency services offered

"Long Roofing went above and beyond when installing our roof and gutter. The job turned out more difficult than we thought it would be but Long Roofing made me feel comfortable and reassured that they would fix everything. Everyone involved from the salesperson to customer service listened to our needs and treated me with respect. The roof looks amazing. I don't want to get into price, but even though you may get someone less expensive, using Log Roofing was well worth a little extra cost"
Roof Replacement
Roof Replacement
Roof Replacement
Roof Replacement
Response time10 mins
33 neighbors recently requested a quote
Recommended by84%of homeowners
Avatar for FRS Roofing
FRS Roofing
4.7(
190
)
Asphalt Shingle Roofing - Install or ReplaceNatural Slate Roofing - RepairMetal Roofing - Install or Replace+12 more

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 2001

Free estimates

Emergency services offered

"Reading the other reviews I'm a bit horrified and thinking about going up and checking by myself, though the roof is pretty steep so I rather live... but we had overall great experience. Quick appointment, believable explanations and the price seemed to be right (we didn't bring anyone else to quote, so cannot state if for 100%). The roof itself seemed to be reasonable, but then we added the chimney cap and that was quoted at $1500 and then lowered to $1200. Is that the right price - I do not know, but since they were already on the roof I assumed asking them is easier than looking for new contractor. The dumpster was left couple of days over - which made our life a bit difficult since it was taking our drive-way, but it was promptly removed upon request. Honestly - I'm very happy with the job and I think I will call them again if I had another roof. One more thing - read very carefully the financing agreement if you financing. I read it and we decided to opt out of it and just pay by credit card. Pretty scary."
Under cunstruction
Truk
Rubber back part
Asphalt shingles part
Rubber Roof on the Back

+38

Response time9 hrs
Response rate91%
33 neighbors recently requested a quote
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Roofing FAQs, answered by experts

It’s possible to install your chimney cap in some areas, but it’s usually better to hire a professional. Before you attempt a DIY chimney cap installation, check to see if your local building department requires a permit. If it does, you should hire a professional to pull the permit and complete the work for you. Even if you don’t need a permit, getting up on your roof is dangerous, especially if you have an aggressive pitch or slippery roof material, like metal. Hiring a chimney professional guarantees the job is done correctly and keeps you safe from injury.

Sometimes chimney caps blow off during storms or fall off after rusting away. While this typically won’t cause structural damage, failing to replace a chimney cap can. A chimney cap prevents moisture, animals, and debris from entering your chimney, all of which can cause serious problems, such as damage to the masonry or blockages in the flue.

Many homeowners believe that a modern home looks better with a flat roof than a sloped roof. A flat roof can provide several aesthetic benefits for modern homes. Among the pros and cons of a flat roof for a modern home design are the clean lines and straight edges that it delivers to improve curb appeal.

No, a chimney crown is not the same as a chimney cap. A chimney crown is a flat cement area on top of a masonry chimney. It starts where the masonry part of the chimney ends at the very top and domes upward toward the flue opening. A chimney cap sits on top of the crown over the flue. It is usually made of metal and allows smoke to escape without letting in rainwater.

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.

The Chestnut Hill, MA homeowners’ guide to roofing services

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