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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
143 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%
32 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
76 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

201 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

40 neighbors recently requested a quote
Recommended by90%of homeowners
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Showing 1-10 of 354
Roofing FAQs, answered by experts

Yes, professionals offer various roofing materials, including shingles and metal, to match home aesthetics.

The purchase price of 3-tab shingles is less than that of other material varieties, such as architectural shingles. However, 3-tab shingles generally last far fewer years than even the least expensive architectural ones. Other roofing types, such as metal or clay, also cost more than 3-tab shingles. However, if you plan to stay in your home for many years, the long-term cost of any of these options can compete with 3-tabs because of their longevity.

The most important thing to remember when laying shingles is to work from the bottom of the slope to the top. This leaves you with a top overlap that directs runoff from one row to the next until it reaches the eave for disposal. You should also make sure you follow the manufacturer's instructions and the local building code for nailing patterns and frequency so all of your hard work stays put through varying weather conditions.

For homeowners who plan to stay in their homes for a long time or never want to have to deal with replacing a roof again, rubber roof shingles are likely worth the added investment amount over asphalt shingle varieties. While the initial cost of installing a rubber shingle roof will be significantly higher, their long life spans can be worth it in the long term. Consider the curb appeal of a rubber roof, though, as other roofing materials, like metal, can look better and offer even greater value.

You can only overlay a roof once. Any additional layers of shingles will add too much weight and may also violate building codes. Once your roof has had an overlay, you’ll need to have a full roof replacement, including a tear-off of all existing roofing materials, when it’s time for a new roof. 

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.