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TRUSTED BY CHESTERTOWN, NY HOMEOWNERS

  • Average homeowner rating star icon4.1
    Average homeowner rating
  • Verified reviews icon54
    Verified roofing services reviews

Find Roofers in Chestertown

"Responded quickly and got the job done. "

Ryan R on December 2025

We are an up coming company working to earn your business. We are dedicated to growing our business by providing fantastic customer service. We do the following: Hood cleaning Soft washing houses Window Washing under two stories Gutter cleaning

"Responded quickly and got the job done. "

Ryan R on December 2025


"This experience went flawless. Isaac was a great estimator and well below many companies in the area. Roofers were professional. Area was cleaned like there was no one there working. A+ from start to finish. I would definitely recommend their services."

Chuck S on June 2025

Goldspire Roofing is a family owned roofing company established in 2018. We saw a need for quality roofers, so we became the solution! Our mission is to do quality work that benefits your lifestyle.

"This experience went flawless. Isaac was a great estimator and well below many companies in the area. Roofers were professional. Area was cleaned like there was no one there working. A+ from start to finish. I would definitely recommend their services."

Chuck S on June 2025


Avatar for Home Evolution Roofing LLC

Home Evolution Roofing LLC

4.92(
227
)
Approved Pro

Home Evolution Roofing LLC

4.92(
227
)
Approved Pro
Super Service Award
Customers say: Quality work
Recommended by 97% of Angi customers
Recommended by 97% of HomeAdvisor customers
26 years of experience

Looking for a reliable roofing contractor? Look no further! We've been in business for over 20 years. Home Evolution Roofing offers free estimates, competitive pricing, warranty, and there are absolutely no hidden charges. Contact us today for all your roofing needs! Financing Available - $0 down

"They did an excellent Job 1 day job replacing my roof, installing a rubber part on my roof and re-pointing my chimney. They are extremely professional, they ensured that all the debris ensuring all the nails and residuals were cleaned up around the house. I highly recommend them for any roofing job you may have. Michael's crew came in 1 day (between 8am till around 6:30) replaced the roof cleaned up and did a wonderful job."

Santo P on November 2025

Looking for a reliable roofing contractor? Look no further! We've been in business for over 20 years. Home Evolution Roofing offers free estimates, competitive pricing, warranty, and there are absolutely no hidden charges. Contact us today for all your roofing needs! Financing Available - $0 down

"They did an excellent Job 1 day job replacing my roof, installing a rubber part on my roof and re-pointing my chimney. They are extremely professional, they ensured that all the debris ensuring all the nails and residuals were cleaned up around the house. I highly recommend them for any roofing job you may have. Michael's crew came in 1 day (between 8am till around 6:30) replaced the roof cleaned up and did a wonderful job."

Santo P on November 2025


Avatar for Home Evolution Roofing

Home Evolution Roofing

4.80(
435
)
Approved Pro

Home Evolution Roofing

4.80(
435
)
Approved Pro
Super Service Award
Customers say: True professional
Recommended by 95% of Angi customers
Recommended by 95% of HomeAdvisor customers
21 years of experience

Home Evolution is your top rated contractor in Albany, NY and greater capital district. Make us your first choice for all your roofing and siding needs. We currently specialize in roof replacement, roof repairs, siding installation and repairs, window installation, attic insulation, skylight replacement and seamless gutter installation. We are an A+ rated Better Business Bureau roofing contractor for the greater Albany, NY area, We are a VELUX certified skylight installation contractor. We are an IKO PRO Shield roofing contractor. Visit our website for more information on the services we offer: https://www.homeevolution.net - Roofing Albany NY

"Job well done. "

Pari T on January 2026

Home Evolution is your top rated contractor in Albany, NY and greater capital district. Make us your first choice for all your roofing and siding needs. We currently specialize in roof replacement, roof repairs, siding installation and repairs, window installation, attic insulation, skylight replacement and seamless gutter installation. We are an A+ rated Better Business Bureau roofing contractor for the greater Albany, NY area, We are a VELUX certified skylight installation contractor. We are an IKO PRO Shield roofing contractor. Visit our website for more information on the services we offer: https://www.homeevolution.net - Roofing Albany NY

"Job well done. "

Pari T on January 2026


Avatar for Herman Exterior Homes, LLC

Herman Exterior Homes, LLC

4.87(
31
)
Approved Pro

Herman Exterior Homes, LLC

4.87(
31
)
Approved Pro
Super Service Award
Customers say: True professional
3 years of experience
Free onsite estimate

We are a Home Exterior renovation company serving upstate New York and Western Mass. Accredited with a Master craftsman certification from Certainteed in both Siding and Roofing, we offer the highest quality craftsmanship and fine detail. Specializing in Roofing, Siding, Window installation and seamless rain gutters. We offer long term financing and 0% short term financing as well for qualified customers!

"Excellent team of installers worked professionally and proficiently. When the roof was complete the whole crew worked on clean-up and left the yard immaculate. On the sales side Brandon was responsive and had excellent communication through the whole process. Santiago mer with us personally at completion to make sure we were happy with the results. I highly recommend Herman Exterior Homes for your next roofing or siding project."

Ray G on July 2025

We are a Home Exterior renovation company serving upstate New York and Western Mass. Accredited with a Master craftsman certification from Certainteed in both Siding and Roofing, we offer the highest quality craftsmanship and fine detail. Specializing in Roofing, Siding, Window installation and seamless rain gutters. We offer long term financing and 0% short term financing as well for qualified customers!

"Excellent team of installers worked professionally and proficiently. When the roof was complete the whole crew worked on clean-up and left the yard immaculate. On the sales side Brandon was responsive and had excellent communication through the whole process. Santiago mer with us personally at completion to make sure we were happy with the results. I highly recommend Herman Exterior Homes for your next roofing or siding project."

Ray G on July 2025


Avatar for Build Right 518

Build Right 518

5.00(
23
)
Approved Pro

Build Right 518

5.00(
23
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
11 years of experience

The Build Right 518, LLC, team goes to every job with over 20 years of experience under their belt. We pride ourselves on our experience, quality, and craftsmanship. Our customers can always rely on us being honest, reliable, and prompt; together, these values make up the foundation of our business. We focus on providing high-quality service and customer satisfaction and we will do everything we can to exceed your expectations. Call us today for a free estimate. cell:518-229-2225

"Best of the best! Not only did they show up when expected , unlike two other local contractors, they gave me a time line is 2 to 3 weeks and completed this project in 6 days! Carpenter's and roofers very professional. Owner/boss on site more than expected. Thank you ALL!!"

Glenn M on October 2024

The Build Right 518, LLC, team goes to every job with over 20 years of experience under their belt. We pride ourselves on our experience, quality, and craftsmanship. Our customers can always rely on us being honest, reliable, and prompt; together, these values make up the foundation of our business. We focus on providing high-quality service and customer satisfaction and we will do everything we can to exceed your expectations. Call us today for a free estimate. cell:518-229-2225

"Best of the best! Not only did they show up when expected , unlike two other local contractors, they gave me a time line is 2 to 3 weeks and completed this project in 6 days! Carpenter's and roofers very professional. Owner/boss on site more than expected. Thank you ALL!!"

Glenn M on October 2024


Avatar for Duell Action Builders

Duell Action Builders

5.00(
3
)
Approved Pro

Duell Action Builders

5.00(
3
)
Approved Pro
11 years of experience
Free onsite estimate

At Duell Action Builders, we bring old-world, quality craftsmanship to every unique project we take on. We specialize in a variety of major home improvement projects to include large and small scale roofing, siding, pole buildings, additions, remodels, major renovations, decks, and home repairs. We work efficiently with our resources to ensure your project is completed on time and on budget. We look forward to building strong, long-lasting relationships with our clients and guarantee your satisfaction. Contact us today and see why we come so highly recommended!

"They installed many floors for us and always do a great job."

Glenda D on January 2026

At Duell Action Builders, we bring old-world, quality craftsmanship to every unique project we take on. We specialize in a variety of major home improvement projects to include large and small scale roofing, siding, pole buildings, additions, remodels, major renovations, decks, and home repairs. We work efficiently with our resources to ensure your project is completed on time and on budget. We look forward to building strong, long-lasting relationships with our clients and guarantee your satisfaction. Contact us today and see why we come so highly recommended!

"They installed many floors for us and always do a great job."

Glenda D on January 2026


Avatar for Freeman Painting

Freeman Painting

5.00(
4
)
Approved Pro

Freeman Painting

5.00(
4
)
Approved Pro
Customers say: Quick response
4 years of experience
Free onsite estimate

Freeman Painting 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.

"Dave was very pleasant. He came to the house, gave me an estimate and started on the day we agreed. Project was a two day project, he came in the morning and worked the second day until the project was completed. If you have any opportunity to work with him you will be pleased. "

David Y on November 2025

Freeman Painting 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.

"Dave was very pleasant. He came to the house, gave me an estimate and started on the day we agreed. Project was a two day project, he came in the morning and worked the second day until the project was completed. If you have any opportunity to work with him you will be pleased. "

David Y on November 2025


Avatar for Elite Contracting

Elite Contracting

5.00(
6
)
Approved Pro

Elite Contracting

5.00(
6
)
Approved Pro
Customers say: Quick response
10 years of experience
Free onsite estimate

Elite Contracting is family owned business. Established in 2015, we have always believed in our commitment to incredible customer service and superior roofing quality. We are not your average roofer. We take extreme passion in what we do, and this is made evident in our customers satisfaction. We stand behind our quality work and our workmanship warranties. Schedule your free estimate with us today!

"Paul is fantastic. He's easy going, helpful. We have a beautiful roof!"

Victoria S on September 2025

Elite Contracting is family owned business. Established in 2015, we have always believed in our commitment to incredible customer service and superior roofing quality. We are not your average roofer. We take extreme passion in what we do, and this is made evident in our customers satisfaction. We stand behind our quality work and our workmanship warranties. Schedule your free estimate with us today!

"Paul is fantastic. He's easy going, helpful. We have a beautiful roof!"

Victoria S on September 2025


Avatar for Sentri Homes

Sentri Homes

New on AngiNew on Angi
Approved Pro

Sentri Homes

New on AngiNew on Angi
Approved Pro
3 years of experience
Free onsite estimate

Sentri Homes is a full-service contractor delivering high-end home additions, whole-home remodels, new custom builds, luxury kitchens, structural framing, roof replacements, and every major renovation. We assign a dedicated project manager to every job, deliver meticulous craftsmanship with clear communication, and back our work with an industry-leading warranty to ensure complete peace of mind on your largest investments. Our in-house team of licensed builders and master craftsmen consistently earns 5-star reviews by turning big visions into stunning, high-value homes—when you need one trusted partner who truly does it all, we’re the proven choice.

Sentri Homes is a full-service contractor delivering high-end home additions, whole-home remodels, new custom builds, luxury kitchens, structural framing, roof replacements, and every major renovation. We assign a dedicated project manager to every job, deliver meticulous craftsmanship with clear communication, and back our work with an industry-leading warranty to ensure complete peace of mind on your largest investments. Our in-house team of licensed builders and master craftsmen consistently earns 5-star reviews by turning big visions into stunning, high-value homes—when you need one trusted partner who truly does it all, we’re the proven choice.

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Roofing questions, answered by experts

Sometimes, a local authority won’t approve a request for a roofing permit. This may be because of incomplete documentation, unclear project plans, processing delays, or insufficient communication. There may also be discrepancies with building codes.

Installing a green roof costs between $10 and $30 per square foot. Green roofs cost slightly more than standard roofs, due to the extra materials and installation know-how required. The type of green roof you choose also impacts the cost, with intensive roofing systems costing considerably more than extensive roofs.

DIY is not recommended, as slate requires specialized handling and proper underlayment installation for durability.

A roof pitch multiplier is an accurate way to calculate roof square footage, and it’s handy for purchasing the correct amount of materials. To determine your roof pitch multiplier, you'll need to calculate the roof slope, square it, and add it to 144. Next, find the square root of the total and divide it by 12. The answer is your roof pitch multiplier. Once you know the roof pitch multiplier, multiply it by the total square feet of your building to determine the total roof surface area.

A new roof will last anywhere from 15 to 150 years, depending on the type of roof you install. Asphalt shingle roofs have the shortest lifespan of 15 to 30 years. Metal roofs usually last for 30 to 60 years, but some materials can fall outside of that range. Clay and concrete roofs can last for 50 to 100 years, and slate roofs have the longest lifespan of 60 to 150 years.

The Chestertown, NY homeowners’ guide to roofing services

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

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