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TRUSTED BY WESTPORT, MA HOMEOWNERS

  • Average homeowner rating star icon4.2
    Average homeowner rating
  • Verified reviews icon630
    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 BusinessSealant for Roof - Apply- For BusinessAsphalt Shingle Roofing - Repair - 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
162 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
31 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%
37 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

141 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 350
Roofing FAQs, answered by experts

Yes, thatched roofs are legal in most areas in the U.S., but you should always check your local building codes to ensure there are no restrictions in your particular area before installing one. Even where they are legal, you’ll usually need to apply fireproofing to the roof to keep it up to code. Keep in mind that a new roof might not increase home value as much if you choose a thatched roof, as they aren’t common in the U.S. and might not be as desirable to many home buyers.

While you can stay at home during a roof replacement, you probably won’t want to, as it’ll be very noisy. The area around your home will also be messy, as roofers will be discarding old roof material and storing their equipment on the ground.

Generally, hailstones that are one inch in diameter or larger can cause significant damage to a roof. However, smaller hail can also cause damage, particularly when accompanied by strong winds, if it strikes an aging or poorly maintained roof, or if hailstorms are frequent in your area. Hail that is ¼ inch (pea-sized) or smaller poses a minimal risk of immediate, permanent damage, but cumulative impacts can cause deterioration over time. The extent of the damage also depends on the roofing material; hail-resistant tiles like slate or certain types of asphalt shingles can withstand impacts better than other materials. If you are concerned about potential damage after a storm, it is always a good idea to have a professional roofer conduct an inspection.

Yes, gable vents can let water in. That being said, this usually only occurs during extreme conditions like heavy rainfall. You can prevent water from entering through gable vents by adding a screen that traps the water before it can enter.

A roof replacement can take anywhere from one to 14 days. For most homes, a full replacement that includes tearing off old materials takes about one to two days, though the average project can last up to 12 days. The exact timeline depends on several factors, including the roof's size and complexity, the type of roofing material, the crew size, and weather conditions. Certain materials take longer to install; for example, metal roofs can take seven to 14 days because the material is more difficult to work with than asphalt shingles, wood, or tile. A re-roofing project, where new shingles are installed over old ones, can take half the time or less. It's also important to factor in the time needed to obtain necessary permits. A professional roofing contractor will typically complete the job faster than a DIY approach.

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.