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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

If a roof is not vented, trapped air and moisture have nowhere to go and will cause moisture to build up in the attic. When moisture builds up, it can cause mold and mildew, leaks, and rot. It will make the space hot and stuffy, which can result in higher energy bills as the HVAC system works overtime to regulate the temperature.

There are several signs that indicate you’ll need new underlayment. Clear signs include missing or damaged roofing and exposing the underlayment to the elements. Additionally, if you notice water damage in your home by the roof after a storm, it could indicate that your underlayment may need to be replaced. If your gutters aren’t draining properly, it could also lead to rotting or water damage to the underlayment.

The ideal color for your roof depends entirely on your preference. If you’re looking for something classic, gray, brown, and black will rarely steer you wrong. A roof with a pop of color like green or red can be sophisticated and elegant when paired with the right colored siding. Decide what vibe you’re looking for and choose a color palette that suits you.

If you need to replace the roof over your attached garage, a roofing contractor can perform what is called a partial roof replacement that only affects garage roofing. However, it's important to keep in mind that only replacing a portion of your roof creates a situation where your roofing has two different lifespans. You will also miss out on the opportunity for a full roof warranty. In some cases, having two different roofs on your home could increase risks for leaks. When replacing the roof on a detached garage, homeowners have the option to make the project bigger by upgrading their home roof alongside their garage roof. However, this isn't necessary if your home has a newer, properly functioning roof. It is better to try to match the new garage roof to your home's existing roof instead.

Gaps between tiles are necessary to help with weatherproofing, allow for thermal expansion, and increase wind resistance. In general, a small gap no larger than 3 millimeters wide will encourage proper drainage and limit cracking. Beyond that, tiles should overlap a minimum of 3 inches, except at the eaves where they should extend to the center of the gutter.

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.