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TRUSTED BY HOLLISTON, MA HOMEOWNERS

  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon1.2k+
    Verified roofing services reviews

Top-Rated Roofers in Holliston - Updated Nov 2026

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 Holliston, 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 DelPrete Home Improvements
DelPrete Home Improvements
4.9(
249
)
Asphalt Shingle Roofing - RepairNatural Slate Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace+26 more

Serving Holliston, MA and surrounding areas

Approved

In business since 1992

Free estimates

Warranties offered

"As I was looking for a company to do my roof, I didn't want just anyone. I wanted someone who would take care of my needs and to replace old with the new. Beantown informed me upfront all the expectations. If there was something needed to added like payment because needs more support, Beantown would tell me along the way and not after the fact. If your looking to get a new roof, Beantown is your place to go. They are fair and reasonable and understand your needs. There is no question to Big or too small that they can't answer. Awesome Work Guys!"
Home exterior makeover. New roof using Owens Corning Trudefinition Duration in Onyx Black. New vinyl siding with Certainteed Monogram in Midnight Blue with White trim. New deck in AZEK Island Oak decking. New Harvey slider. New Thermatru  doors.
Deck Upgrade in Halifax, MA. Old deck boards were removed and new AZEK decking in Island Oak with Premier White railings were installed.
Final photo of pool deck pressure treated wood and AZEK decking in Coastline.
Final photo. We stripped the existing roof and removed the heat wire. We inspected the roof deck for rotted wood and replaced. Next we installed Owens Corning Roofing System including Trudefinition Duration Shingles in Onyx Black. Heat wire was reinstalled.
Stripped existing siding and replaced any rotted wood. Installed Henry Blueskin water barrier underlayment. Next we installed James Hardie fiber cement smooth plank siding in Monterey Taupe. New homeowner painted PVC rake boards and fascia were also installed along with new gutters in Eggshell.

+744

3 neighbors recently requested a quote
Recommended by100%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 - Install or Replace+19 more

Serving Holliston, MA and surrounding areas

Approved

In business since 1984

Free estimates

Emergency services offered

"Initially they were responsive and got to the job quickly. They started one day later than their initial estimate and finished the job in a day and a half. The roof has gone through the Arthur downpour with no apparent leaks.
The cleanup wasn't perfect, as there were small pieces of old roofing and cellophane strips left on the ground. In a couple of places where the roof changed direction the shingles didn't conform fully to the shape leaving some gaps. Also, when they reflashed around the chimney they put the new flashing one course above the old flashing, rather than digging out the old flashing and inserting the new material in the same place.
When I called about the issues they were pleasant, but it took a few weeks for a representative to come out and review things, and then three more weeks for them to come to resolve the first two issues. The flashing is just the way they do things and is OK.


"
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
Avatar for Cook's Roofing
Cook's Roofing
4.7(
44
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For Business+26 more

Serving Holliston, MA and surrounding areas

Approved

In business since 1975

Warranties offered

Customers say: True professional

"Mr. Cook responded promptly to my request for an estimate on my roofing job. He arrived as promised and provided a very thorough and fair estimate for the work requested, which was re-roofing the house, a garage, an addition and a shed, adding a 27' section of gutter to my garage and replacing two skylights in my addition. He was professional and personable, as well as very knowledgeable. The estimate he provided was complete and fair. In addition, he provided a list of homes he had roofed (with shingle colors) so that I could get a good idea of the color in actual lighting conditions. I was very pleased with his interaction and have no doubt as to his capability. Unfortunately, you can only hire one firm and I opted for a different company but you should contact him for an estimate on your job. He is well established and would be competitive."
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New Roof for a home in Upton, Massachusetts with Moire Colored CertainTeed Shingles
New Roof for a Home in Mendon, MA. CertainTeed Shingles in Colonial Slate Color Blend

+2

Response time1 day
16 neighbors recently requested a quote
Recommended by97%of homeowners
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Roofing FAQs, answered by experts

Most roof leaks occur where shingles meet or where there are sealants or seams in the materials. This is common around skylights and at any point there is a break in the roof such as corners and edges. Roofing materials are incredibly strong and resistant when overlapping, but any change in that can cause gaps where water can enter.

Whether replacing the entire roof or just installing roof shingle replacements in small areas, always pull up the old roof shingles. While you can technically put new roof shingles (but not other roof materials) over old shingles, this can add weight strain to the roof and prevent the new shingles from securing properly to the roof.

Clay tile roofing is common for traditional villas, while flat roofs are more standard for modern villa homes. Clay tile roofs are long-lasting, require little maintenance, and are great for warmer climates. Flat roofs are usually low-cost, energy-efficient, and allow for rooftop gardens. 

Before hiring a roofing contractor, it's wise to ask several key questions. Inquire if they are licensed for roof replacement and repair and if they hold any special certifications. Ask if they will be completing all the work themselves or subcontracting parts of it. It's also important to understand the project timeline, whether they will remove the old roof or place new shingles on top, and how they will handle cleanup after the project is complete. Finally, ask about warranties for both work and materials, what recourse you have if issues like leaks arise, and if they can provide customer references.

The best kind of tarp for a roof is one that will stand up to the elements, weather, and sun. Viny roof tarps are known for their durability and resistance to water, tears, and mold—making these tarps a good choice for use in winter conditions and the summer sun. Polyethylene tarps are also quite durable and waterproof.

The Holliston, MA homeowners’ guide to roofing services

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