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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

"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."
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

"First our salesman Vincent was very considerate and temporarily fixed our roof until they were able to come and replace our roof. He also advised us on small loan companies to help pay for the new roof. They came to replace the roof earlier than they originally thought. Everyone we dealt with was very professional. We are very happy without beautiful new roof."
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%
100 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
1830 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
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
37 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%
23 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

Most roof leaks occur where shingles meet or where there are sealants or seams in the materials. This is common around skylights and at any point there is a break in the roof such as corners and edges. Roofing materials are incredibly strong and resistant when overlapping, but any change in that can cause gaps where water can enter.

Copper roofing works well in all kinds of climates, but it’s ideal in humid climates because it naturally repels fungus, moss, and algae. This makes it one of the best roofing options for Cape Cod homes in the Northeast, as well as homes in the humid southern states and snowy northern states. That said, copper is vulnerable to thermal expansion. If you live in a climate that has extreme temperature changes, your contractor will need to consider this during the installation process.

Clay tile roofing is more susceptible to damage from impact than something like a metal roof or even asphalt shingles, so they aren’t ideal in areas that see frequent windblown debris or hail. Clay tile roofs are also an average of $8,000 more expensive than asphalt shingle roofs, so up-front cost is an important consideration to make before committing.

Most traditional lenders will not loan against a house with a leaking roof, and some lenders won’t lend against a home with a roof near the end of its lifespan. If the roof on your new home is in poor condition, you may need to have the seller offer a credit for a roof replacement after closing, or you can opt for a renovation loan—also called a 203k loan—to bundle the house and the roof replacement into one loan.

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 Chestertown, NY homeowners’ guide to roofing services

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