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TRUSTED BY WINCHENDON, MA HOMEOWNERS

  • Average homeowner rating star icon4.2
    Average homeowner rating
  • Verified reviews icon272
    Verified roofing services reviews

Find Roofers in Winchendon

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

Serving Winchendon, 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
166 neighbors recently requested a quote
Recommended by84%of homeowners
Avatar for East Coast Metal Roofing, LLC - Massachusetts
East Coast Metal Roofing, LLC - Massachusetts
4.6(
104
)
Metal Roofing - Install or Replace

Serving Winchendon, MA and surrounding areas

Approved

In business since 2015

Free estimates

Warranties offered

"The cost of metal roof is more than asphalt but this roof comes with 50 year guarantee. Since this is our third roof , I wish we had this option years ago. Roof looks great"
Halifax, MA - Dawn Gray Aluminum Shingle
Griswold, CT - Dawn Gray Aluminum Shingle
Southborough, MA - Black Aluminum Shingle
Rindge, NH - Classic Brown Aluminum Shingle
Webster, MA - Black Aluminum Shingle

+155

Response time2 days
74 neighbors recently requested a quote
Recommended by92%of homeowners
Avatar for JP Carroll Roofing
JP Carroll Roofing
5.0(
10
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For Business

Serving Winchendon, MA and surrounding areas

Approved

Super Service Award Winner

In business since 1988

Free estimates

Warranties offered

JP Carroll is the most trusted roofing company in MA and CT - serving our communities for almost 40 years with over 500 5-star reviews. \n\nWhile all roofs will eventually face problems and fail, homeowners can take many preventative measures to protect their roofs so they last as long as possible. The most important action is to find a professional roofer you can rely on when something goes wrong. Whether you need roof repair, inspection, ice damming prevention, you can count on our trained and certified roofers in Connecticut and Massachusetts for high-quality service every time. As full-service contractor, JP Carroll Roofing is the best choice for prompt and dependable residential and commercial roofing service. We also offer siding, gutter, gutter guard, and replacement window installation as well as gutter cleaning.

JP Carroll Roofing
JP Carroll Roofing
JP Carroll Roofing
JP Carroll Roofing
JP Carroll Roofing

+13

Avatar for Overstate Roofing Services Inc.
Overstate Roofing Services Inc.
4.3(
62
)
Asphalt Shingle Roofing - RepairFlat, Foam or Single Ply Roofing - RepairSealant for Roof - Apply+11 more

Serving Winchendon, MA and surrounding areas

Approved

In business since 2025

Free estimates

Emergency services offered

"Needed a roof inspection done for my business. They handled my case with care and were very polite and knowledgeable. They gave me the official documents I needed and made sure all the details were available to me about what was going on with my roof."
Roof replacement
Roof replacement
1393 neighbors recently requested a quote
Recommended by1%of homeowners
Avatar for Clear Choice Home Improvements, LLC
Clear Choice Home Improvements, LLC
4.5(
977
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or Replace

Serving Winchendon, MA and surrounding areas

Approved

In business since 2004

Free estimates

Credit card accepted

"Fast, efficient, had to stop twice for a rain shower and did my roof in 6 hrs and 45 mins start to finish including clean up. Roof is almost 1800 sq ft. The job supervisor was here for the entire thing. They are awesome"
Before & After
Before & After
Before & After
Before & After
Before & After

+6

Response time3 hrs
60 neighbors recently requested a quote
Recommended by92%of homeowners
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Showing 1-10 of 262
Roofing questions, answered by experts

A cool roof is any heat-reflecting roof that rejects solar energy more efficiently than traditional roofing (staying about 50 degrees cooler). Thanks to this ability, a cool roof will make your home cooler on a hot, sunny day. Cool roofs come in a variety of materials, including asphalt, wood, or polymer shingles, clay or concrete tiles, metal, and more.

Metal roofs do not inherently leak more than shingle roofs; when properly installed, they are generally less likely to leak. Asphalt shingle roofs are more susceptible to leaks due to factors like wind uplift, damage from extreme weather, moss growth, and ice dams. Over time, asphalt shingles also lose their protective grit, which reduces their waterproofing capabilities. In contrast, metal is a more resilient material that stands up better to heavy precipitation and high winds. However, metal roofs can develop leaks if they are poorly installed, have improperly sealed fasteners, or experience issues from thermal expansion. For this reason, professional installation and regular maintenance are crucial to ensure a metal roof's longevity and superior protection against leaks.

Whether or not the terms of your roofing estimate are negotiable depends on the contractor. Some professional roofers will be willing to budge on labor fees to some extent, while others will simply walk away from the potential work rather than lower their fees. In most cases, it’s best not to negotiate the terms, as lower labor charges could lead to your contractor cutting corners. Material costs aren’t negotiable, but you could purchase them yourself to try to save on delivery fees and markups.

If your roof is nearing the 20-year mark in age, you probably should start worrying about the roof’s longevity. If you don’t know the age, it may be time to figure out who installed your roof, so you can estimate the age accurately. You then can make plans to pay for the upcoming roof replacement. You also can learn how to inspect a roof yourself to look for signs of damage that may indicate a need for a replacement.

Always inform your insurance company when you get a new roof. A new roof may entitle you to lower rates or discounts, and if you need to make a claim, they’ll have up-to-date information on your roof. You’ll need to provide documentation—ask your insurance agent what you need to submit to prove you had your roof replaced.

The Winchendon, MA homeowners’ guide to roofing services

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