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TRUSTED BY CHESTERTOWN, NY HOMEOWNERS

  • Average homeowner rating star icon4.2
    Average homeowner rating
  • Verified reviews icon57
    Verified roofing services reviews

Top-Rated Roofers in Chestertown - Updated Nov 2026

Avatar for Home Evolution Roofing LLC
Home Evolution Roofing LLC
4.7(
273
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairFlat, Foam or Single Ply Roofing - Repair+2 more

Serving Chestertown, NY and surrounding areas

Approved

Super Service Award Winner

In business since 2000

Free estimates

Warranties offered

"Mike and crew were top notch ! From start to finish Home Evolution exceeded our expectations!! They completed our roof in one day and they did an amazing job ! Communication was great from start to finish, professionalism of the crew was amazing ! They left the outside of our home cleaner than when they arrived ! If you are considering a new roof , look no further than Home Evolution ! Their prices are affordable and the work is impeccable!"
ROOFING
ROOF & SIDING
ROOF & SIDING
Response time7 hrs
Response rate100%
4 neighbors recently requested a quote
Avatar for Home Evolution Roofing
Home Evolution Roofing
4.5(
552
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairInspection - Roofing+1 more

Serving Chestertown, 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."
Roof Replacement in Ballston Spa NY
Roof Replacement in Niskayuna NY
Roof Replacement in Glenmont NY
Roof Replacement in Slingerlands NY
Roof Replacement in Athens, NY

+20

Response time7 hrs
Response rate92%
95 neighbors recently requested a quote
Avatar for King Quality Roofing and Siding
King Quality Roofing and Siding
4.5(
20
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairMetal Roofing - Install or Replace+10 more

Serving Chestertown, NY and surrounding areas

Approved

In business since 1988

Free estimates

Emergency services offered

King Quality Roofing and Siding is proud to be a locally owned and operated business that has been serving the community since 1988! With years of experience and unmatched expertise, we can help with any and all of your roofing and siding needs. Since opening our doors we have built our business on providing customers with the highest quality products and craftsmanship, at a fair price. You can count on our team to be timely, tidy, and when the job is done, that you will be 100% satisfied with the work completed. Let us show you the King Quality difference, get in touch today!

North Babylon Home After
North Babylon Home Before
Jeff and Crew
Beach house Shake Shingles
Beach house Shake Shingles

+1

Response time1 day
1817 neighbors recently requested a quote
Recommended by80%of homeowners
Avatar for Spaulding Construction
Spaulding Construction
4.7(
14
)
Asphalt Shingle Roofing - Install or Replace

Serving Chestertown, NY and surrounding areas

Approved

In business since 2019

Customers say: True professional

We take great pride in our experience, expertise, quality, and customer service that we provide to meet the consumer’s needs. It is our mission to provide excellent workmanship and complete customer satisfaction from start to completion of a project. In order to understand the needs and expectations of our customers, we take great care to work and communicate with every customer in a professional manner. Our reputation is based on service, safety, and quality, regardless of how large or small the job.

Crown point build
Crown point build
Crown point build
Crown point build
Crown point build

+14

12 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for Herman Exterior Homes, LLC
Herman Exterior Homes, LLC
4.7(
38
)
Flat, Foam, or Single Ply Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessFlat, Foam, or Single Ply Roofing - Install or Replace- For Business

Serving Chestertown, 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%
470 neighbors recently requested a quote
Roof Maxx
4.5(
6
)
Asphalt Shingle Roofing - RepairSealant for Roof - ApplyRoof - Clean+4 more

Serving Chestertown, 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
41 neighbors recently requested a quote
Recommended by66%of homeowners
Avatar for Elite Contracting
Elite Contracting
4.4(
7
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair+21 more

Serving Chestertown, NY and surrounding areas

Approved

In business since 2016

Free estimates

Emergency services offered

"They installed a gorgeous new roof for us. The whole crew was very professional and courteous. Having once worked for a roofing company, I checked the quality of the installation and I can say that I couldn't find anything that wasn't done exactly how it should have been done! Highly recommend this roofing company in Albany NY."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+1

Response time2 days
Response rate100%
24 neighbors recently requested a quote
Avatar for Gregg Construction
Gregg Construction
4.3(
13
)
Flat, Foam or Single Ply Roofing - Repair- For BusinessFlat, Foam, or Single Ply Roofing - Install or Replace- For Business

Serving Chestertown, NY and surrounding areas

Approved

In business since 2001

Free estimates

Emergency services offered

We are 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.\nDon't replace your metal roof until you have us evaluate it. Most of the time we can Restore it!

Recommended by91%of homeowners
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Roofing FAQs, answered by experts

The warranty for algae-resistant shingles varies by manufacturer, but the industry standard is 25 years for overall shingle durability and lifespan and between 10 and 15 years for algae resistance. Some products come with longer warranties for discoloration of up to 30 years. Check warranty coverage for the shingle and algae protection before deciding on a roofing product.

The four types of roof sheathing are plywood, oriented strand board (OSB), planks, and tone-and-groove boards. The overwhelming majority of homes use the first two (especially OSB) and the other two are not often seen outside of special use cases. Methods of sheathing include solid sheathing, open sheathing where there are gaps, and plank sheathing. Most roofs are solid sheathing.

You’re going to need a permit for nearly every roof-raising project. This is a very important step, as the work you’re doing has serious safety considerations. Professionals are the ones to handle this type of work—including sourcing the permits—as they have the expertise required to perform the work safely. Insurance and warranty are usually voided if you do this work without a permit, and you may even be required to halt construction and tear it down as a penalty for working without a building permit.

Heated roofs are a preventative measure and don’t have an outsized effect on your home’s value, so there is no definitive answer to this question. If you diligently monitor your roof in colder months, ensuring there is never snow or ice buildup then no, maybe they aren’t worth it. However, who really watches their roof every day or goes out in freezing weather to rake the roof? For most people worried about roof damage in the winter, heated roofs are a good investment. 

The lifespan of an impact-resistant roof averages 30 to 50 years, depending on the quality of the shingles and the amount of wear and tear it endures. Some high-quality shingles may last even longer. For comparison, a standard asphalt roof lasts about 20 years, so choosing an impact-resistant option can increase your roof's lifespan by 50% or more, particularly in regions prone to extreme weather.

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.