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TRUSTED BY WINCHENDON, MA HOMEOWNERS

  • Average homeowner rating star icon4.2
    Average homeowner rating
  • Verified reviews icon285
    Verified roofing services reviews

Top-Rated Roofers in Winchendon - Updated Nov 2026

Avatar for Global Home Exteriors, Inc.
Global Home Exteriors, Inc.
4.8(
86
)
Flat, Foam, or Single Ply Roofing - Install or Replace- For BusinessAsphalt Shingle Roofing - Repair - For BusinessSealant for Roof - Apply- For Business+2 more

Serving Winchendon, MA and surrounding areas

Approved

In business since 2017

Free estimates

Emergency services offered

"Very prompt and organized. Andrea came out during the day while they were working on the roof to check on progress and to see if there were any questions. She also followed up by email to see if we had any questions and was very transparent on the extra cost of having to replace some of the decking. Will definitely use them again in the future if need be!"
Roof Replacement
Roof Underlayment
Roof Installation
Roof Prep & Install
Shingle Installation

+1

Response time3 days
152 neighbors recently requested a quote
Recommended by97%of homeowners
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
35 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
75 neighbors recently requested a quote
Recommended by92%of homeowners
Avatar for Adam Vaillancourt Roofing & Gutters - Milford
Adam Vaillancourt Roofing & Gutters - Milford
4.9(
13
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Install or ReplaceHeating Cable for Roof - Install+6 more

Serving Winchendon, MA and surrounding areas

Approved (Corporate)

Super Service Award Winner

In business since 2004

Free estimates

Small jobs welcome

"Called Adam Vaillancourt Roofing to fix a leak in our roof based on their consistently high customer satisfaction ratings. We met with sales rep Jose Luna, who conducted a thorough inspection and found the leak easily. His presentation about the company and how they do their work was impressive and Jose was very professional and included a video that Jose shot while on our roof in which he explained not just the issues that were found but WHY the work was needed. He never pressured us into agreeing to anything. We signed a contract immediately. Fast forward a few weeks later and Paul Camarro and his crew showed up at the house on time and ready to work. When they were done, Paul showed us photos of the completed repair work, so I knew they delivered as promised. We will absolutely be calling Vaillancourt in a few years when our roof needs to be replaced. Highly recommend!"
During
During 2
Before
After
After

+7

Response time12 hrs
Response rate100%
86 neighbors recently requested a quote
Avatar for Overstate Roofing Services Inc.
Overstate Roofing Services Inc.
4.2(
80
)
Asphalt Shingle Roofing - RepairFlat, Foam or Single Ply Roofing - RepairSealant for Roof - Apply+10 more

Serving Winchendon, MA and surrounding areas

Approved

In business since 2025

Free estimates

Emergency services offered

"5 Stars ! I hired Overstate multiple times . Yani was so polite and professional , I needed to replace my plaster ceilling in 4 different rooms . It started in a small project and slowly I decided working with Yani on a new bathroom remodel , framing and other drywall services . I know that overstate does roofing as well , I?ll definitely consider them when I replace my new roof ."
Roof replacement
Roof replacement
1696 neighbors recently requested a quote
Recommended by1%of homeowners
Avatar for McGrath Roofing & Exteriors
McGrath Roofing & Exteriors
5.0(
6
)
Asphalt Shingle Roofing - Install or ReplaceFlat, Foam, or Single Ply Roofing - Install or ReplaceMetal 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 Vault Roofing
Vault Roofing
4.2(
50
)
Asphalt Shingle Roofing - Repair

Serving Winchendon, MA and surrounding areas

Approved (Corporate)

In business since 1979

Free estimates

Credit card accepted

For homeowners who want to feel confident in their roofing decision, Vault Roofing is the most dependable roofing and gutter replacement company. Vault delivers lasting peace of mind through thoughtful craftsmanship, earned trust, and long-term value, supported by an industry-leading lifetime warranty. \n

Stunning Curb Appeal
Stunning Curb Appeal
Stunning Curb Appeal
Stunning Curb Appeal
Stunning Curb Appeal

+6

49 neighbors recently requested a quote
Recommended by42%of homeowners
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Showing 1-10 of 268
Roofing FAQs, answered by experts

Many insurance policies will not cover a roof with two layers of shingles. An additional layer of shingles increases the risk of various kinds of damage, and insurers typically won’t pay claims on a roof with an overlay. Adding a layer of shingles may even jeopardize your insurance coverage entirely, so check your policy to ensure you stay within coverage guidelines. 

Roof repairs average around $1,100 but can easily exceed that for larger repairs. The cost of roof replacement depends on the size of your home and the materials used but averages between $4,000 and $24,000.

Roofing felt is the most common type of roof underlayment, likely because it has been around the longest. It’s called roofing felt because it is often made of felt soaked in asphalt. Depending on the type of roofing a home has, roofing felt comes in different thicknesses. 

If properly installed and maintained, roofing felt should last between 10 and 25 years. 

Roofers can install roof vents. Updating, upgrading, or simply replacing your roof's existing vents is common when installing a new roof. If you're looking to upgrade your ventilation system with a powered version, a local HVAC professional can also help with the task. If adding roof vents to your home is necessary while installing an addition or during other renovation work, your contractor will handle or hire out the venting work.

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.

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.