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TRUSTED BY VINEYARD HAVEN, MA HOMEOWNERS

  • Average homeowner rating star icon4.5
    Average homeowner rating
  • Verified reviews icon121
    Verified roofing services reviews

Top-Rated Roofers in Vineyard Haven - Updated Nov 2026

Avatar for Willard Co
Willard Co
4.6(
164
)
Metal Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair+26 more

Serving Vineyard Haven, MA and surrounding areas

Approved

In business since 1873

Free estimates

Emergency services offered

"It could not have gone better. The crew came on time and worked late each day. A few days were extremely hot, but they worked through it. When the job was finished, two neighbors told me that they watched the progress, and each neighbor commented that the crew was very hard working. One said, "I've never seen such a hard-working crew. Each person knew his specific job and they worked together seamlessly." Also, several neighbors have stopped me to say that they love the look of the new roof and new gutters."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+13

Response rate100%
19 neighbors recently requested a quote
Recommended by95%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 Vineyard Haven, 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
77 neighbors recently requested a quote
Recommended by92%of homeowners
Avatar for JP Carroll Roofing - Foxborough
JP Carroll Roofing - Foxborough
4.8(
18
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairInspection - Roofing

Serving Vineyard Haven, MA and surrounding areas

Approved

In business since 1988

Free estimates

Credit card accepted

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.

Recent Roofs
Recent Roofs
Recent Roofs
Recent Roofs
Recent Roofs

+14

195 neighbors recently requested a quote
Avatar for Bel Islands Home Improvement, LLC
Bel Islands Home Improvement, LLC
5.0(
10
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Repair - For Business

Serving Vineyard Haven, MA and surrounding areas

Approved

In business since 2001

Free estimates

Emergency services offered

"I recently hired Andrei and his crew for a new roof installation. Andrei was incredibly easy to work with. He was VERY accommodating to my timeline, was accessible when I had questions and followed up with project updates as they became available. EVERYTHING you want in a contractor! Would def hire again. A++"
New roof
New roof
Response time1 day
21 neighbors recently requested a quote
Recommended by100%of homeowners
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 Vineyard Haven, 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
1743 neighbors recently requested a quote
Recommended by1%of homeowners
Avatar for Express Home Restoration
Express Home Restoration
5.0(
10
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair - For Business

Serving Vineyard Haven, MA and surrounding areas

Approved

In business since 2024

Free estimates

Emergency services offered

We pride our company on reliability, great communication, integrity, and quality work. We are experts in our trade and will do our best to keep you as educated as we can on your particular task or project. We look forward to earning your business! Book with us online or feel free to give us a call today! \n

Roof Projects
Roof Projects
Roof Projects
Roof Projects
Roof Projects

+44

Response time4 hrs
Response rate93%
5 neighbors recently requested a quote
Avatar for Craig Dias
Craig Dias
5.0(
7
)
Asphalt Shingle Roofing - RepairMetal Roofing - RepairRoof - Clean

Serving Vineyard Haven, MA and surrounding areas

Approved

"Craig was very efficient, explained how he would do the project. Then he made sure that we were on the same page before he started. His appraisal reflects honest, realistic market rates rather than overcharging. In addition he was very polite."
Chimney cap
Red copper Bay Window
Standing Seam Copper Roof
Faucet Replacement
Faucet Replacement

+1

26 neighbors recently requested a quote
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Roofing FAQs, answered by experts

While you can technically install TPO roofing over an existing roof, it isn't always wise to do so. The more layers of material you add to your roof, the more weight it must support. You may also develop moisture issues by covering your existing roof with TPO. Your local building codes and regulations may actually require you to remove the existing roof before adding TPO, so check with your local municipality.

Unfortunately, there’s no definitive answer to this question, but the wind rating of your shingles will give you a good idea of what wind speeds can damage your roof. If you’re concerned about damage, inspect your roof following windy conditions to look for signs of wind damage to your shingles. When in doubt, consider hiring a professional who fixes roofs to carry out an expert inspection. Remember that hurricanes, tropical storms, and tornadoes are likely to cause the most damage, but even severe thunderstorms can bring winds that compromise your roofing system.

Copper roofing works well in all kinds of climates, but it’s ideal in humid climates because it naturally repels fungus, moss, and algae. This makes it one of the best roofing options for Cape Cod homes in the Northeast, as well as homes in the humid southern states and snowy northern states. That said, copper is vulnerable to thermal expansion. If you live in a climate that has extreme temperature changes, your contractor will need to consider this during the installation process.

Asking questions before hiring a roofer ensures you receive the best quality for your investment upfront and in the long term. Roofers with minimal experience, unfamiliar with local building codes, or minimal access to great materials can lead to both structural and financial problems down the line. You should also be able to easily communicate and collaborate with your roofer during extensive projects.

Wood shake roofs are durable, energy-efficient, and offer a natural aesthetic. Composite options provide similar looks with less maintenance.

The Vineyard Haven, MA homeowners’ guide to roofing services

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