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Best siding pros near Chestertown, NY

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  • Average homeowner rating star icon3.8
    Average homeowner rating
  • Verified reviews icon11
    Verified siding services reviews

Top-Rated Siding pros in Chestertown - Updated Nov 2026

Avatar for Herman Exterior Homes, LLC
Herman Exterior Homes, LLC
4.7(
38
)
Vinyl Siding - Install or Completely ReplaceWood or Fiber-Cement Siding - Install or Completely Replace

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%
448 neighbors recently requested a quote
Avatar for King Quality Roofing and Siding
King Quality Roofing and Siding
4.5(
20
)
Vinyl Siding - Install or Completely ReplaceVinyl Siding - Repair or Partially Replace

Serving Chestertown, NY and surrounding areas

Approved

In business since 1988

Free estimates

Emergency services offered

"I hired King Quality only 2 weeks ago and within the 2 weeks they came to my home, gave me a price, installed the siding and left my house spotless. I was very nervous making the initial call but they put my mind at ease. It was a pleasure working with them from my 1st call into the office speaking to the ladies then speaking with Jeff to the crew foreman Billy. They definitely lived up to there name. I received King quality!"
North Babylon Home After
North Babylon Home Before
Jeff and Crew
Beach house Shake Shingles
Beach house Shake Shingles

+1

Response time1 day
2019 neighbors recently requested a quote
Recommended by80%of homeowners
Avatar for Mountainside Maintenance
Mountainside Maintenance
5.0(
5
)
Vinyl Siding - Repair or Partially ReplaceWood or Fiber-Cement Siding - Repair or Partially Replace

Serving Chestertown, NY and surrounding areas

Approved

In business since 2025

Free estimates

Small jobs welcome

"Fast response to my request for assistance, showed up on time to look over the job and produce a timely estimate. On the day of work, arrived on time, worked efficiently and did a very good job. followed up a day or two after to make sure we were satisfied. I would use this gentleman again."
Wet bar/Drink area
Wet bar/Drink area
Wet bar/Drink area
Wet bar/Drink area
Wet bar/Drink area

+12

Avatar for M&N Construction Group, LLC
M&N Construction Group, LLC
4.7(
27
)
Vinyl Siding - Install or Completely ReplaceWood or Fiber-Cement Siding - Install or Completely Replace

Serving Chestertown, NY and surrounding areas

In business since 2012

Free estimates

Offers commercial services

"Their work is of the highest quality. Both Erwin and Dan were fantastic to work with. They were quick to start the job and finish it once we gave them the go a head to begin. Bill was a pleasure to work with as well. They cleaned up better than it was when they came. I would highly recommend them."
Response time9 hrs
Response rate90%
Recommended by95%of homeowners
Avatar for Jon Spaulding
Jon Spaulding
4.9(
11
)
Metal Siding: Install or Completely ReplaceMetal Siding: Repair or Partially ReplaceSiding Installation or Repair+4 more

Serving Chestertown, NY and surrounding areas

In business since 2019

Free estimates

Emergency services offered

"Jon recently replaced a dated drop ceiling in my kitchen with Armstrong ceiling planks and added puck lights to complete the upgrade. Looks fantastic!! Very responsive and easy to work with from the initial consult to finishing the job and going beyond my expectations."
Roofing Project
Hardwood Flooring Sales/Installation/Refinishing Project
Roofing Project
Roofing Project
Roofing Project

+117

Recommended by100%of homeowners
Avatar for High Tech Construction Co
High Tech Construction Co
4.3(
43
)
Metal Siding: Install or Completely ReplaceMetal Siding: Repair or Partially ReplaceSiding Installation or Repair+4 more

Serving Chestertown, NY and surrounding areas

In business since 1987

Free estimates

Emergency services offered

"We shopped and spoke with many "facade restoration experts" before choosing to work with High Tech and we are so glad we did our research. Shaiful was by far the most knowledgeable contractor we spoke with and made us feel confident that he was capable of solving our issues.  When it was clear that there was no saving our original cornice, he offered up more than one suitable way forward. We decide to let his crew re-create the original piece from stone. The work they did left us with a beautiful and artistic facade the functions well in collecting rain water from the roof. The crew was respectful, clean and on time. They went above and beyond all of our expectations in touching up every minor detail so that the whole front of the house was left looking brand new. We could not be happier. Our home looks better than we could have imagined. I recommend High Tech Construction with no hesitation. 
"
Facade Restoration - High Tech Construction Co
stoop restoration -high tech construction co
Wood Stoop
Limestone Stoop
brownstone stoop and facade restoration

+20

Recommended by81%of homeowners
Avatar for Adirondack Home Builders
Adirondack Home Builders
5.0(
5
)
Metal Siding: Install or Completely ReplaceMetal Siding: Repair or Partially ReplaceSiding Installation or Repair+4 more

Serving Chestertown, NY and surrounding areas

Free estimates

Credit card accepted

"This is a truly wonderful business. Jay was absolutely incredible, punctual, a hard worker and got it done fast with such passion and beautiful work! We are so thrilled with our new home remodeling projects at a very fair price for the work. We will be hiring this company again for any new ideas we have!"
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+11

Recommended by100%of homeowners
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Siding FAQs, answered by experts

Similar to other types of wood siding consisting of natural materials, cedar siding should last 20 to 40 years. However, the lifespan for any wood siding, including cedar, can be far shorter without the proper repair and maintenance work. Don’t put off making repairs, or problems could worsen quickly. While you can repair minor holes and cracks in the siding shakes, rot and warping requires replacing the boards. 

Yes, you can mount shutters to vinyl siding. Depending on the weight and material of choice, you may need more fasteners or larger fasteners to secure the shutters onto the vinyl surface. It’s also important to locate studs or drill into the window frame when installing heavier shutters to best hold the weight of the shutters if you opt for composite or wood shutters.

The best types of siding to withstand hail are fiber cement siding and engineered wood siding. Fiber cement siding is known for impact resistance, while some brands of engineered wood siding can withstand hail as big as 1 and 3/4 inches with no marks. Vinyl and aluminum siding are the most susceptible to hail.

Consider your home's architectural style, neighborhood guidelines, and the vendor's options. Samples and software previews can help visualize the final result.

The best type of paint for vinyl siding is a high-quality acrylic latex paint, often labeled as '100% acrylic.' This type of paint is lightweight and adheres well to the vinyl surface, which reduces the likelihood of it peeling or flaking. For best results, apply two coats and avoid using thick paint. The color choice is also important; select a light color to prevent the paint from absorbing excess heat, which helps extend the durability of your paint job.

The Chestertown, NY homeowners’ guide to siding services

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