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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

Find Roofers in Chestertown

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%
8 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."
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Roof Replacement in Slingerlands NY
Roof Replacement in Athens, NY

+20

Response time7 hrs
Response rate92%
83 neighbors recently requested a quote
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

8 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for King Quality Roofing and Siding
King Quality Roofing and Siding
4.5(
19
)
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
1031 neighbors recently requested a quote
Recommended by80%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%
537 neighbors recently requested a quote
Roof Maxx
4.5(
6
)
Asphalt Shingle Roofing - RepairRoof - CleanSealant for Roof - Apply+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
72 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 questions, answered by experts

There are several pros and cons of flat roofs. One disadvantage of flat roofs is that you lose potential attic space because it's flat. Flat roofs tend to pool water and because they lack an angle, any leak in the roof—usually due to a bad seal—has the potential to let in a lot of water. They don’t work well in climates with snow. Flat roofs are also structurally weaker than sloped roofs.

Whether replacing the entire roof or just installing roof shingle replacements in small areas, always pull up the old roof shingles. While you can technically put new roof shingles (but not other roof materials) over old shingles, this can add weight strain to the roof and prevent the new shingles from securing properly to the roof.

Due to the complexity and weight of tiles, DIY is not recommended. Professional installation ensures proper alignment and durability.

A well-maintained tile roof can last anywhere from 40 to over 100 years, with its exact lifespan depending on the material and level of care. Proper maintenance, which includes keeping the roof clean, free of debris, and performing routine repairs for any cracked tiles, is crucial for longevity. The lifespan varies significantly by tile type:

  • Clay, terracotta, and slate tiles are highly durable and can last over 100 years.

  • Concrete tiles typically last from 30 to 100 years.

  • Metal tile roofs generally last between 40 and 70 years.

  • Composite tile roofs have a lifespan of 20 to 50 years.

Be aware that maintenance for a tile roof can sometimes be more expensive than for an asphalt roof.

Roof blistering and hail damage are different in their physical appearance. Blistering, often caused by inadequate ventilation, low-quality material, and improper installation, looks like large, irregular bubbles popping out of your roof. Meanwhile, hail damage is usually circular or oval dents entering your roof and often follows the same path as the hail storm.

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.