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  • 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
41 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

"OTB was great to deal with. Wind storm ripped half the shingles off of my garage, Chris came out the next day to give me a quote. Price was excellent and the job was done a week later. His contractor was well informed and professional, and left my home looking better than ever. I would highly recommend using them for any project."
Front
Back
Side 1
Side back
After

+21

Response time9 hrs
Response rate100%
2 neighbors recently requested a quote
Avatar for Adam Vaillancourt Roofing & Gutters - Milford
Adam Vaillancourt Roofing & Gutters - Milford
4.9(
13
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Install or ReplaceHeating Cable for Roof - Install+6 more

Serving Winchester, NH and surrounding areas

Approved (Corporate)

Super Service Award Winner

In business since 2004

Free estimates

Small jobs welcome

"Called Adam Vaillancourt Roofing to fix a leak in our roof based on their consistently high customer satisfaction ratings. We met with sales rep Jose Luna, who conducted a thorough inspection and found the leak easily. His presentation about the company and how they do their work was impressive and Jose was very professional and included a video that Jose shot while on our roof in which he explained not just the issues that were found but WHY the work was needed. He never pressured us into agreeing to anything. We signed a contract immediately. Fast forward a few weeks later and Paul Camarro and his crew showed up at the house on time and ready to work. When they were done, Paul showed us photos of the completed repair work, so I knew they delivered as promised. We will absolutely be calling Vaillancourt in a few years when our roof needs to be replaced. Highly recommend!"
During
During 2
Before
After
After

+7

Response time12 hrs
Response rate100%
85 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

"Our project is scheduled for completion. The initial phase of receiving an estimate and securing financing has been very smooth and easy. Maddy Delisle was extremely attentive and patient working with us getting the project through the financing phase. She went above and beyond in answering our numerous questions. If you have a roofing or home improvement project ask for Maddy."
11 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 - RepairAsphalt Shingle Roofing - Install or Replace

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

1 neighbors recently requested a quote
Avatar for Clear Choice Home Improvements, LLC
Clear Choice Home Improvements, LLC
4.5(
980
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or Replace

Serving Winchester, NH and surrounding areas

Approved

In business since 2004

Free estimates

Warranties offered

"I'm a return customer. They did our replacement windows a few years ago, and they just replaced our asphalt roofing shingles. They did a wonderful job. I was amazed and impressed with how quickly, and how well, they completed the job. I love my new roof."
 Insulated Vinyl Siding
 Seamless Gutters
 Easy to clean vinyl replacement windows
  Asphalt Roofing
 Leaf Slugger Gutter Covers and Water Management

+114

Response time2 hrs
216 neighbors recently requested a quote
Recommended by91%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

49 neighbors recently requested a quote
Recommended by42%of homeowners
Avatar for BHI Roofing
BHI Roofing
5.0(
9
)
Asphalt Shingle Roofing - Install or ReplaceMetal 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
7 neighbors recently requested a quote
Recommended by33%of homeowners
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Showing 1-10 of 181
Roofing FAQs, answered by experts

Clay tile roofing is common for traditional villas, while flat roofs are more standard for modern villa homes. Clay tile roofs are long-lasting, require little maintenance, and are great for warmer climates. Flat roofs are usually low-cost, energy-efficient, and allow for rooftop gardens. 

Asphalt roofs provide better insulation than metal roofs, but that doesn’t always mean that asphalt roofs are better for reducing heating and cooling bills. In hotter climates, metal roofs will usually be better for home efficiency because the material reflects more sunlight and reduces solar heat gain. In colder climates, asphalt roofs are sometimes superior in terms of efficiency because they introduce more solar heat gain to your home and have greater insulating capabilities. However, metal roofs installed with an air gap can provide similar levels of insulation.

There should be small gaps between your roof and the walls of your home, and other buildings. These small gaps let building materials shift, expand, and contract with weather and other outside forces, and they prevent moisture from wicking down walls from roofing and gutter systems. Without these strategic gaps, your home’s exterior and its finishes can sustain water damage, decay, peel, delaminate, and crack. However, there is a fine line between a smart gap and a problematic gap—all  gaps should be small, intentional, and covered or filled in with foam insulation to prevent pests from using them as access points.

Roofers don’t typically replace vent pipes themselves, but they do handle the flashing and seals around vent pipes when working on a roof. During a roof replacement or repair, roofers inspect the vent pipe flashing for damage, replace deteriorated seals, and ensure the pipe is properly integrated into the roofing system to prevent leaks. If the vent pipe itself is cracked or damaged, a plumber is usually required to replace it, while the roofer ensures the roofing components around the pipe remain watertight.

Moving a chimney is possible, but it is a very complex process that requires professional expertise, knowledge of building codes, and safety protocols. Most homeowners find it easier to remove the fireplace and build a new fireplace and chimney in the new location of your home. Talk to your chimney pro about all your options, their costs, and pros and cons. 

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.