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

Avatar for Long Home
Long Home
4.3(
96
)
Asphalt Shingle Roofing - Install or Replace

Serving Winchendon, MA and surrounding areas

Approved

In business since 1945

Free estimates

Emergency services offered

"The workers that removed and replaced my roofs had fantastic work ethics. They did a wonderful job and left my yard nail free and debris free. I will recommend them to anyone I know that needs a roof or any other home repair."
Roof Replacement
Roof Replacement
Roof Replacement
Roof Replacement
Response time10 mins
33 neighbors recently requested a quote
Recommended by84%of homeowners
Avatar for BBS General Construction Inc
BBS General Construction Inc
4.6(
14
)
Asphalt Shingle Roofing - Install or Replace

Serving Winchendon, MA and surrounding areas

Approved

In business since 2016

Free estimates

Emergency services offered

"the work was great, he went in their and cleaned up everything, and put in a piece of pad to cover it to keep the birds out; he also checked every part of the roof for any possible entries as well."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+16

Response time10 hrs
11 neighbors recently requested a quote
Recommended by78%of homeowners
Avatar for Vault Roofing
Vault Roofing
4.1(
50
)
Asphalt Shingle Roofing - Install or Replace

Serving Winchendon, MA and surrounding areas

Approved (Corporate)

In business since 1979

Free estimates

Warranties offered

"The work was done exactly as expected. Tom Schmidt,the representative, was personable and trustworthy. I will recommend him to any of my friends or neighbors if they want roofing advice."
Stunning Curb Appeal
Stunning Curb Appeal
Stunning Curb Appeal
Stunning Curb Appeal
Stunning Curb Appeal

+6

54 neighbors recently requested a quote
Recommended by31%of homeowners
Avatar for Clear Choice Home Improvements, LLC
Clear Choice Home Improvements, LLC
4.5(
977
)
Asphalt Shingle Roofing - Install or Replace

Serving Winchendon, MA and surrounding areas

Approved

In business since 2004

Free estimates

Credit card accepted

"Clear Choice's crew was in and out in a few hours. They removed my current roof and replaced with with new shingles. The workers were diligent and polite and did a great job cleaning up the area when they were done. I am very impressed with the work and would certainly suggest them to other looking to get their roof replaced or any other home improvement project."
Before & After
Before & After
Before & After
Before & After
Before & After

+6

Response time3 hrs
129 neighbors recently requested a quote
Recommended by92%of homeowners
Avatar for McGrath Roofing & Exteriors
McGrath Roofing & Exteriors
5.0(
6
)
Asphalt Shingle Roofing - Install or Replace

Serving Winchendon, MA and surrounding areas

Approved

Free estimates

Emergency services offered

Warranties offered

"McGraths did ma great job for us on several different roof projects including metal roofing on a porch addition, metal replacement roof on a bedroom wing, and a roof reconfiguration over our mud room/entrance. Most recently they have added a roof over a closet addition to the mud room/entrance."
Metal Roof Princeton
Metal Roof Princeton
Metal Roof Princeton
Asphalt Roof Replacement
Asphalt Roof Replacement

+20

3 neighbors recently requested a quote
Avatar for Northeast Home & Energy, Inc.
Northeast Home & Energy, Inc.
4.4(
50
)
Asphalt Shingle Roofing - Install or Replace

Serving Winchendon, MA and surrounding areas

Approved

In business since 1980

Free estimates

Emergency services offered

"Overall, the roof looks great. However, the job did get off to a rocky start because there was no supervision on site the 1st day. Once supervision arrived all issues were corrected and the job went well. I recommend you stay home and watch every step of the installation to insure it is going as planned. (I would recommend this with any roofing contractor) Their crew moves very quickly. Jack Sullivan handled the contract and ultimately delivered as promised."
Roof Replacement Milford
Roof Replacement Milford
Roof Replacement Milford
Roof Replacement Milford
Roof Replacement Milford

+24

Response time4 days
Recommended by43%of homeowners
Avatar for Capital Construction Contracting South
Capital Construction Contracting South
4.2(
69
)
Asphalt Shingle Roofing - Install or Replace

Serving Winchendon, MA and surrounding areas

Approved

In business since 2004

Free estimates

Credit card accepted

"Outstanding company from the sales person to the project manager to the very competent roofers. The estimate to replace my roof was not the highest or the lowest but was realistic. I was in constant contact with various personnel who kept me informed about the project. On installation day, the crew of 8 roofers began work at 7:30am and finished at 2:30pm. All waste was cleaned up and placed in the dumpster. Overall, a great company to consider when replacing your roof."
Before and After: Siding
Before and After: Siding
Before and After: Siding
587 neighbors recently requested a quote
Recommended by77%of homeowners
DaBella - Westborough (Roofing)
3.6(
591
)
Asphalt Shingle Roofing - Install or Replace

Serving Winchendon, MA and surrounding areas

Approved

In business since 2011

Free estimates

Warranties offered

"I had a great experience with DaBella’s roof inspection. The representative was professional, knowledgeable, and took the time to thoroughly inspect my roof. They explained everything clearly, showed me photos of the areas they examined, and answered all of my questions without any pressure."
7 neighbors recently requested a quote
Recommended by88%of homeowners
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Showing 1-10 of 126
FAQs for asphalt shingle roofing installation and replacement projects in Winchendon, 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 Winchendon, 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.