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Best roofers near Chestertown, NY

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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%
104 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
1883 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%
459 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
32 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
Avatar for Erie Home
Erie Home
4.4(
73
)
Asphalt Shingle Roofing - Install or Replace

Serving Chestertown, NY and surrounding areas

Approved (Corporate)

In business since 1976

Free estimates

Credit card accepted

Erie Home Basement Solutions is a division of Erie Home?a national leader in home improvement since 1976. We have long been known for offering industry-leading solutions to our customers? most pressing needs, and our basement waterproofing, foundation repair, and crawl space services are no exception. When it comes to protecting your home against structural problems, why put the project in anything less than the most capable of hands? At Erie Home Basement Solutions, we provide the effective repair services and personalized service you need to have complete peace of mind.

Basement Projects
Basement Projects
Basement Projects
Basement Projects
Basement Projects

+32

13 neighbors recently requested a quote
Recommended by92%of homeowners
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Showing 1-10 of 104
Roofing FAQs, answered by experts

During the framing process, builders connect the roof to the walls with materials, including metal connectors, plywood panels, and wood blocks. These roof-to-wall connections are important and provide weatherproofing, noise and temperature insulation, protection against pests, and home integrity. The type of connector and method used will vary, depending on your home’s construction and needs, and each has pros and cons in terms of cost, noise insulation, longevity, and reliability. Talk with your home or roofing contractor about the best connectors for your roof and walls, and what they recommend for your home.

You can put a green roof on a regular house with a compatible slope. Green roofs are best suited for flat or gently sloped roofs, as steeply pitched roofs can make the installation and maintenance of the green roof challenging. Flat roofs can support the weight of the soil and plants and ensure effective drainage.

Roofers don’t typically replace vent pipes themselves, but they do handle the flashing and seals around vent pipes when working on a roof. During a roof replacement or repair, roofers inspect the vent pipe flashing for damage, replace deteriorated seals, and ensure the pipe is properly integrated into the roofing system to prevent leaks. If the vent pipe itself is cracked or damaged, a plumber is usually required to replace it, while the roofer ensures the roofing components around the pipe remain watertight.

Costs vary by repair scope, materials needed, and labor, with average repairs ranging from $300 to $1,000, contingent on roof size.

Flapping shingles, or shingles that are lifting or curling away from your roof, can be glued back into place using roofing cement or sealant. Apply the glue underneath the shingle, then press it down firmly. You can leave a brick on top of the shingle to hold it in place overnight while the sealant dries.

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.