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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
40 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%
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

"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 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
223 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
Avatar for Sion Roofing
Sion Roofing
5.0(
5
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair

Serving Winchester, NH and surrounding areas

Approved

In business since 2024

Free estimates

Warranties offered

Sion Roofing is dedicated to providing our customers with the best quality and craftsmanship. We are here to build relationships with our customers and communities and to provide our employees with a great place to work. We look forward to working with you!!

ROOF INSTALLATION
ROOF INSTALLATION
ROOF INSTALLATION
ROOF INSTALLATION
ROOF INSTALLATION

+19

Response time5 days
Response rate100%
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Roofing FAQs, answered by experts

It’s the reverse of home de-winterization. To winterize, you purge your plumbing system (including your water heater and all piping) of water. Some experts also recommend filling fixtures with an antifreeze solution. Other tasks involve winterizing sprinklers, sealing foundation vents, check weatherproofing around doors and windows, and more.

The most obvious and severe sign of a roof leak is the presence of wet spots on your ceilings, specifically on the top floor of your home. You can also identify a roof leak from your attic if you see sagging insulation or if you notice mold growth or water stains on the rafters or the underside of the roof deck. From the street, look for cracked or missing shingles, moss growth, and shingles that are curling upward, all of which can suggest a leak.

You should definitely be wary of roofing contractors who offer significantly lower prices than their competitors. Most roofers in the area are all dealing with the same cost of materials, and labor costs are often comparable, too. If they’re significantly cheaper than other companies around, it could be a scam. Read reviews and ask other roofing companies and contractors if they’ve heard of the suspected scamming company.

You can replace a roof in the winter, though it’s not the most popular time to do so. The biggest drawback of winter roofing work is the weather. Snow and ice make for dangerous, slippery working conditions. Plus, shingles can only be installed in temperatures above 40 to 45 degrees. 

The best time to replace a roof is in the spring or fall when the weather is mild. However, you can likely save some money by booking the job in the winter off-season, when roofers have more availability. 

When choosing a roofer to install a green roof, look for someone with experience who specializes in green roofs. Rather than looking for a standard roofing contractor, you'll want to find a company that specifically offers green roofs. That company will have people on staff, such as a landscape architect, who understand the types of plants that thrive on rooftops.

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.