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TRUSTED BY WINCHESTER, NH HOMEOWNERS

  • Average homeowner rating star icon4.4
    Average homeowner rating
  • Verified reviews icon99
    Verified roofing services reviews

Top-Rated Roofers in Winchester - Updated Nov 2026

Avatar for East Coast Metal Roofing, LLC - New Hampshire
East Coast Metal Roofing, LLC - New Hampshire
4.4(
32
)
Metal Roofing - Install or Replace

Serving Winchester, NH and surrounding areas

Approved

In business since 2015

Free estimates

Warranties offered

"I knew from the start I wanted a metal roof and that I wanted the Permalock product for its quality and durability, and that it looked like the shingle roof we had. The lifetime guarantee and product sold me. The roofers were great, and every night the place was cleaned up, very efficient company."
Pomfret Center, CT
Pomfret Center, CT
Pomfret Center, CT
Pomfret Center, CT
Pomfret Center, CT

+4

Response time9 hrs
37 neighbors recently requested a quote
Recommended by94%of homeowners
Avatar for OTB REMODELING
OTB REMODELING
5.0(
16
)
Metal Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace

Serving Winchester, NH and surrounding areas

Approved

Super Service Award Winner

In business since 2024

Free estimates

Emergency services offered

"Really needed a new roof after this winter. These guys were knowledgeable and got me on their schedule relatively fast. Workmanship was high quality and the crew was extremely professional. Absolutely will call again when it is time to replace my siding."
Front
Back
Side 1
Side back
After

+21

Response time9 hrs
Response rate100%
2 neighbors recently requested a quote
Avatar for JP Carroll Roofing - Western Mass
JP Carroll Roofing - Western Mass
5.0(
10
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairInspection - Roofing

Serving Winchester, NH and surrounding areas

Approved

Super Service Award Winner

In business since 1988

Free estimates

Warranties offered

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.

JP Carroll Roofing
JP Carroll Roofing
JP Carroll Roofing
JP Carroll Roofing
JP Carroll Roofing

+13

84 neighbors recently requested a quote
DaBella - Salem (Roofing)
3.5(
622
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair+4 more

Serving Winchester, NH and surrounding areas

Approved

In business since 2011

Free estimates

Credit card accepted

"I meet with two lovely women that explain their company . And about their roofing product and how it works . An there people are factory certified people . It was very interesting and sounds like a great warranty ."
9 neighbors recently requested a quote
Recommended by84%of homeowners
Avatar for RoofSmith New England LLC
RoofSmith New England LLC
5.0(
5
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair

Serving Winchester, NH and surrounding areas

Approved

Free estimates

Emergency services offered

Warranties offered

RoofSmith New England was built to challenge the way roofing has traditionally been sold. We're the David taking on Goliath—an independent, locally owned company proving that honesty, integrity, fair pricing, and exceptional craftsmanship still matter.\n\nWe believe homeowners deserve straight answers, transparent pricing, and quality work without the high-pressure sales tactics, inflated promises, or runaround.\n\nFrom roof repairs to complete replacements, we bring big-company professionalism with small-business accountability. Your home isn't just another job number, and your trust isn't something we take for granted.\n\nNo games. No pressure. No shortcuts. Just Roofing Done Right.

Before & After
Rindge Roof Upgrade
Finished Roof
New Shingle Roof
Roof Upgrade

+1

2 neighbors recently requested a quote
Avatar for BHI Roofing
BHI Roofing
5.0(
9
)
Asphalt Shingle Roofing - Install or Replace

Serving Winchester, NH and surrounding areas

Approved

In business since 2009

Free estimates

Credit card accepted

"Crew showed up right on time as advertised to replace my shed roof Completed the job quickly and efficiently with exceptional care cleaning up Very personal and professional work men Replace roof at a very fair price I will contact this company again for any further home improvement"
Logo
3 neighbors recently requested a quote
Recommended by33%of homeowners
Avatar for Vault Roofing
Vault Roofing
4.2(
50
)
Asphalt Shingle Roofing - Repair

Serving Winchester, NH and surrounding areas

Approved (Corporate)

In business since 1979

Free estimates

Credit card accepted

For homeowners who want to feel confident in their roofing decision, Vault Roofing is the most dependable roofing and gutter replacement company. Vault delivers lasting peace of mind through thoughtful craftsmanship, earned trust, and long-term value, supported by an industry-leading lifetime warranty. \n

Stunning Curb Appeal
Stunning Curb Appeal
Stunning Curb Appeal
Stunning Curb Appeal
Stunning Curb Appeal

+6

48 neighbors recently requested a quote
Recommended by42%of homeowners
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Showing 1-10 of 182
Roofing FAQs, answered by experts

Flat roofs are cost-effective, offer usable space, and are easy to maintain. Foam and single-ply materials provide excellent insulation and durability.

The easiest way to tell if your roof vent boot is leaking is to look in your attic for signs of water damage. You might see visible moisture, water spots, or mold on the roof decking around the roof vent or damaged or soggy insulation below it. If you don’t have access to your attic or aren’t sure if the vent boot is the issue, hire a professional to come inspect your roof and figure out the underlying issue.

Roofing estimates vary for many reasons, but the most significant ones include differences in the cost of labor based on the contractor’s experience and overhead costs, as well as the quality of the materials your roofer will use for the job. You should get your estimates itemized and make sure your contractors include details about the materials they plan on using. Doing so allows you to compare not only based on the cost but also the value that you’ll get for your money.

Installing solar panels involves drilling small holes in your roof to secure the solar panel mounting brackets. These brackets hold the solar panels in place and must withstand strong weather conditions so they’re secured into your roof. However, holes and screws are sealed to prevent leaking and further damage.

Fall is generally considered the best time of year for roof repairs. The weather is temperate and typically drier, which makes for safer working conditions and fewer delays. The days are also still long enough to complete the work.

Spring is another good option and is a popular time for repairs to fix damage from winter storms. However, frequent rainfall can slow down progress. Spring may be a less busy season for roofers than fall.

Summer can also work for roof repairs, but extreme heat can make asphalt shingles too soft and difficult to work with.

The Winchester, NH homeowners’ guide to roofing services

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