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TRUSTED BY CANAAN, NY HOMEOWNERS

  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon68
    Verified roofing services reviews

Top-Rated Roofers in Canaan - Updated Nov 2026

Avatar for S & G Roofing
S & G Roofing
4.8(
95
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair+10 more

Serving Canaan, NY and surrounding areas

Approved

In business since 1998

Free estimates

Emergency services offered

"Judy and I were most pleased with the professional work and the price Eric gave us for a new roof. The hard working crew of 7, with 5 nail guns “blazing,” stripped our 3 roofs, replaced rotted plywood and completed the major part of their work within one day. The crew supervisor Bob was most pleasant to deal with, and Mr Singh came the next day to tackle some of the remaining carpentry issues. Having done a bit of the roofing on our house in my younger years, I appreciate the first rate quality of work."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+2

Response time2 days
3 neighbors recently requested a quote
Recommended by93%of homeowners
Avatar for Home Evolution Roofing
Home Evolution Roofing
4.5(
552
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairInspection - Roofing+1 more

Serving Canaan, NY and surrounding areas

Approved

Super Service Award Winner

In business since 2005

Free estimates

Warranties offered

"Project was to remove old roof material and install new asphalt shingles on my Bolton landing home. Andre, Sergio and the crew did a picture perfect job. When they left, beside the great looking roof, youâ d never know they were there. From my first contact through the completion, they communicated clearly every step of the way. I would recommend Home Environment to anyone."
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Roof Replacement in Athens, NY

+20

Response time7 hrs
Response rate92%
110 neighbors recently requested a quote
Avatar for Xterior Solutions
Xterior Solutions
4.7(
316
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or Replace

Serving Canaan, NY and surrounding areas

Approved

In business since 2011

Free estimates

Emergency services offered

"Our experience with Xterior Solutions went very well. We inquired about getting a roof replacement and they quickly contacted us and scheduled an initial visit. The rep provided an overview of what would be done, explained the materials that would be used and provided an estimate of what the work would cost. We then took a few weeks to explore the different roofing colors to determine which one we'd like best on our house. We visited their small showroom to view samples, borrowed samples to take back to our house and even drove by a few homes that had prior work by Xterior Solutions to see the shingles. After deciding to move forward with the project, the provided a tentative start date and later contacted us a few days before the start date to confirm and provide some information on what to expect while the work was in progress. The crew showed up as expected on the start date and was able to strip and replace our entire roof in one day. The were able to protect a flower garden near the house by draping tarps over the plantings. After the roof was installed, the yard was clean up very well and the roof looks great! Xterior Solutions completed the work as promised, and were very easy to work with at each step in the process."
The arial before view of the roof
Before
Before
Roof Replacement
Before

+100

Response time6 hrs
Response rate100%
9 neighbors recently requested a quote
Avatar for ProEdge Remodeling - Roofing
ProEdge Remodeling - Roofing
4.3(
47
)
Asphalt Shingle Roofing - Install or Replace

Serving Canaan, NY and surrounding areas

Approved

In business since 1961

Free estimates

Credit card accepted

ProEdge Remodeling is a family-run window, door, roof and bath replacement company serving residents in Rhode Island, Connecticut, Massachusetts, New Hampshire, New Jersey and New York. Founded in 1961, ProEdge has decades of local home remodeling expertise and strong ties to the community, and is proud to be a BBB® Accredited Partner with an A+ rating.\n\nAs the premier home improvement company in New York and New England, we offer energy-efficient windows, custom exterior doors, premium roofing, and expert bath remodeling, all installed by certified local professionals.\n\nAll ProEdge products are backed by industry leading warranties, including a lifetime 25-year transferable warranty on window parts and labor. With over 60 years of experience, ProEdge delivers high-quality, custom solutions designed to enhance your home for a lifetime.\n\nYou can request a free quote online or call to schedule a free consultation with a ProEdge Remodeling professional to discuss options and pricing.

Asphalt Shingle Roofing
Asphalt Shingle Roofing
Recommended by85%of homeowners
Avatar for JAF Contracting
JAF Contracting
5.0(
8
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For Business+22 more

Serving Canaan, NY and surrounding areas

Approved

In business since 2010

Free estimates

Emergency services offered

At JAF Contracting, we take pride in providing dependable roofing and home improvement services to Pittsfield and all of Berkshire County. Built on a foundation of craftsmanship, honesty, and reliability, we’re committed to helping homeowners protect and enhance their properties with quality work that lasts.\nWhether we’re installing a new roof, repairing storm damage, or tackling a full renovation, we treat every project with the same attention to detail and respect we’d expect for our own homes. Our team brings years of experience and a strong local reputation to every job, delivering results you can count on — on time and on budget.\n\nWhen you work with JAF Contracting, you're choosing a crew that values integrity, stands behind its work, and cares about the community we serve.

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Work Photos
Work Photos
Work Photos
Work Photos

+5

7 neighbors recently requested a quote
Avatar for Herman Exterior Homes, LLC
Herman Exterior Homes, LLC
4.7(
38
)
Flat, Foam, or Single Ply Roofing - Install or ReplaceFlat, Foam, or Single Ply Roofing - Install or Replace- For BusinessAsphalt Shingle Roofing - Install or Replace - For Business

Serving Canaan, NY and surrounding areas

Approved

Super Service Award Winner

In business since 2023

Free estimates

Emergency services offered

"Herman Exterior Homes more than exceeded my expectations. I received 3 estimates and they were the lowest of the 3 by a significant amount. More importantly than the price was responsiveness. Brandon kept in constant contact with me throughout the process. I cannot sing their praises enough. I would highly recommend them for any roof job, big or small."
Response time9 hrs
Response rate97%
446 neighbors recently requested a quote
Roof Maxx
4.5(
6
)
Asphalt Shingle Roofing - RepairRoof - CleanSealant for Roof - Apply+4 more

Serving Canaan, NY and surrounding areas

Approved

In business since 2024

Free estimates

Credit card accepted

"They explained to me that they may not be able to help me. The roof was pretty dirty With Pete Moss so they cleaned the roof and realize that the roof was too far gone for the service and they didnâ  t even charge me for the roof cleaning to my surprise . I would definitely recommend this company. they were on time, courteous, and very respectful. Definitely suggest using this company."
Response time4 days
29 neighbors recently requested a quote
Recommended by66%of homeowners
Avatar for Clover Construction
Clover Construction
4.6(
46
)
Asphalt Shingle Roofing - RepairSealant for Roof - ApplyFlat, Foam or Single Ply Roofing - Repair+6 more

Serving Canaan, NY and surrounding areas

Approved

In business since 2015

Free estimates

Credit card accepted

Clover Construction is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers' interests, and make their concerns the basis of our business.

Clover Construction
39 neighbors recently requested a quote
Recommended by85%of homeowners
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Roofing FAQs, answered by experts

Once framing is complete, you will need the following materials to roof a house:

  • Wood sheathing

  • Drip edge, a.k.a metal flashing

  • Underlayment for waterproofing

  • Roof covering, like metal or asphalt shingles

Yes, in many cases, homeowners insurance does cover roof damage caused by snow. For instance, if your roof collapses during a snowstorm or an ice dam results in a ceiling leak, your policy should cover repair costs. However, for a claim to be approved, the roof must have been well-maintained and in good condition before the snow-related damage occurred. The payout, whether full or partial, can also vary depending on the age of your roof and its overall condition prior to the snowfall. It is always best to review your specific homeowners insurance policy to understand the details of your coverage and any potential exclusions.

Yes, removing a chimney is a difficult and major undertaking. Chimneys often provide structural support to a home, so if it's a load-bearing structure, you'll need to take extra precautions to maintain your home's integrity. A project of this complexity typically requires a structural engineer, a masonry contractor, and a demolition crew. The removal process may involve taking the chimney out brick by brick from inside the walls. The cost for chimney removal can range from $2,000 to $10,000, depending on the job's complexity. Due to the difficulty and cost, some homeowners opt to remove the fireplace and seal the chimney at the top and bottom, sometimes also removing the visible exterior portion at the roofline.

Walking on an asbestos roof can pose a risk. Asbestos roofing materials can become brittle over time, increasing the chances of them breaking or releasing fibers when stepped on. Additionally, walking on an asbestos roof without proper precautions can cause further damage to the material. If possible, avoid touching an asbestos roof in any way and consult with a professional about removing and replacing the roof. 

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. 

The Canaan, NY homeowners’ guide to roofing services

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