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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
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 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%
34 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

"Clear communication through the whole process. Questions were answered promptly and the roof looks amazing. I was extremely impressed with the work ethics of the crew, as well as the care the project manager and quality control team gave us."
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 - 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

179 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

"Working with Care Free Homes was a pleasure. On top of donating their services to Habitat for Humanity, they also took the time to coordinate a material donation as well. They took care of all the material ordering and completed the roofs of our duplex quickly. The project came out beautifully!"
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 353
Roofing FAQs, answered by experts

If you’re building the roof trusses yourself, which isn’t recommended, it will be more affordable than buying pre-built trusses. Trusses cost more because they use the same amount of material, but you’ll also be paying for the labor, as well as the delivery to your home. However, if you’re having a contractor build the roof for you, then trusses will be less expensive, as the labor costs to build roof framing on-site will cost more.

Architectural shingles typically last between 20 and 30 years, though most homeowners should plan on replacing them every 20 to 25 years. While some manufacturers offer warranties for 30 to 50 years, especially for extreme weather, achieving such a long lifespan is rare. The actual lifespan can be shorter in areas prone to strong winds, hailstorms, or other extreme weather. It is recommended to replace your roof before it reaches the end of its life to reduce the risk of roof failure, leaks, and costly property damage. Scheduling regular roof inspections will help you determine your roof's remaining life and identify the best timeline for replacement.

EPDM roofs have a few common problems, most of which can be resolved with regular maintenance. This type of roofing is laid down in sheets with seams, which can be a starting point for leaks. Proper installation and roof sealing can often avoid seam issues. 

The material is also susceptible to tears and punctures from falling branches or other sharp objects. There are black and white versions of EPDM, and the black version is more prone to fade and succumb to UV damage. Regular roof inspections can protect the costs of rubber roof installation and extend the life of your roof.

Ridge vents can last as long as your roof does. As long as your ridge vents were installed correctly by a qualified professional, they will need very little upkeep. Inspecting your ridge vents annually to ensure they aren’t cracked, clogged, or leaking will help prolong their lifespan. 

Yes, Energy Star roofs are one of the best types of roofs for cost efficiency. They can reduce your peak cooling demand by anywhere from 10% to 15%.

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.