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TRUSTED BY WESTPORT, MA HOMEOWNERS

  • Average homeowner rating star icon4.2
    Average homeowner rating
  • Verified reviews icon634
    Verified roofing services reviews

Top-Rated Roofers in Westport - 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 Westport, MA and surrounding areas

Approved

In business since 2017

Free estimates

Emergency services offered

"I had a leak that can be seen from a ceiling. Called several roofing companies and got no reply back. Used home advisor and have Andrea called me and scheduled the visit promptly for Freddy to come and check the leak. Freddy was very professional, identified the leak that was due to improper seal of one of the skylights and fixed it right away. He also checked my other skylights and some had the same problem which he fixed. Freddy checked my roof for issues and provided tips for maintenance so it can last long. Definitely will recommend Global Home Improvement, Inc as a honest and very professional company !"
Roof Replacement
Roof Underlayment
Roof Installation
Roof Prep & Install
Shingle Installation

+1

Response time3 days
150 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 Westport, 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 United Home Experts & United Painting Co
United Home Experts & United Painting Co
4.4(
186
)
Asphalt Shingle Roofing - Install or Replace

Serving Westport, MA and surrounding areas

Approved

In business since 1998

Free estimates

Warranties offered

"it went great. After I called them, I didn't have to wait a long time for an appointment. The gentlemen providing the service was professional and courteous. He didn't try to sell me something I didn't need but made me aware of the overall condition of the roof."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+10

Response time1 day
Response rate100%
33 neighbors recently requested a quote
Avatar for East Coast Metal Roofing, LLC - Massachusetts
East Coast Metal Roofing, LLC - Massachusetts
4.6(
104
)
Metal Roofing - Install or Replace

Serving Westport, 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 Westport, 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

189 neighbors recently requested a quote
Avatar for Care Free Homes, Inc.
Care Free Homes, Inc.
4.4(
143
)
Asphalt Shingle Roofing - Install or Replace

Serving Westport, MA and surrounding areas

Approved

In business since 1978

Free estimates

Warranties offered

"They did a fantastic job. From one of the owners, Nathan who came to my house, surveyed my roof and gave me a no nonsense quote to the crew of workers who replaced my roof it was A+ all the way. Paul’s crew was very organized and worked methodically to complete each section of my roof. They cleaned up after themselves every day and left my property spotless when they were finished. I absolutely recommend them for your project."
My jobs
My jobs
My jobs
My jobs
My jobs

+4

38 neighbors recently requested a quote
Recommended by90%of homeowners
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Roofing FAQs, answered by experts

You should tarp a roof whenever roof damage occurs. Missing shingles and holes in your roof can cause roof leaks and problems that come with them. Tarping is a quick way to provide temporary roof protection while you wait for a professional roofer to make repairs.

You can technically install a metal roof over asphalt shingles, but it isn’t a good idea. This is because you’re essentially creating a moisture barrier under the metal, which can easily—and often does—lead to significant mold damage. Removing an asphalt roof isn’t terribly expensive, and some roofing companies might cut you a serious labor and disposal discount if you add it to a new install.

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.

Here are a few tips on how to choose a roofer:

  • Get everything in writing

  • Ask for insurance, license, and bond, then verify them

  • Check their reviews 

  • Ask for recommendations

  • Get multiple quotes

You’ll also want to watch out for any red flags like:

  • Pushy sales tactics

  • Not willing to show necessary documentation

  • Bad gut instincts

Condensation can occur on the inside of a roof, but it should always be temporary. It does not necessarily mean there is a roof leak. Condensation happens when the inside and outside of a house are at different temperatures. For instance, if it is hot during the day and then gets very cold at night, the inside of the house will be warmer than the outside and may cause condensation to form on the inside of the attic. This may not be cause for concern, but if it is happening frequently, it should be addressed; otherwise, it could cause roof leaks, compromise the structural integrity of the wood, or allow mold to grow.

The Westport, MA homeowners’ guide to roofing services

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