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TRUSTED BY CHESTERTOWN, MD HOMEOWNERS

  • Average homeowner rating star icon4.5
    Average homeowner rating
  • Verified reviews icon125
    Verified roofing services reviews

Find Roofers in Chestertown

Avatar for CHESAPEAKE ROOFING WINDOWS & SIDING
CHESAPEAKE ROOFING WINDOWS & SIDING
4.9(
106
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 1987

Free estimates

Warranties offered

"I am extremely satisfied with the product and services. The installation was efficient and properly done. I have used this company before for roofing and trust their work."
Additional Photos
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+45

Response time1 day
Response rate86%
4 neighbors recently requested a quote
Avatar for Roofing Pups, Roofing & Siding
Roofing Pups, Roofing & Siding
4.7(
66
)

Serving Chestertown, MD and surrounding areas

Approved (Corporate)

Super Service Award Winner

In business since 1994

Free estimates

Credit card accepted

"Informative and friendly first meeting, complete with detailed photos of the entire roof and an explanation of the process, followed by 1-day installation of a new roof, with excellent workmanship and a hardworking crew."
Roof Install
ROOFING PUPS
ROOFING PUPS
ROOFING PUPS
PROJECTS

+4

Response time1 day
Response rate93%
322 neighbors recently requested a quote
Avatar for Spicer Bros. Construction Inc.
Spicer Bros. Construction Inc.
4.6(
78
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2002

Free estimates

Warranties offered

"Pete and his team did an outstanding job from the moment they arrived until the final clean-up. What a hard working team! Pete did a great job communicating with me prior to the job and updating me throughout the day during the job. We love our new roof and the quality job! We were impressed with the clean up...not a single piece of trash was left behind!! I would highly recommend Pete and his team for any roofing job and would be pleased to serve as a reference to any potential future clients of Spicer Brothers."
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A sleek new shower with white simulated tile walls and chrome fixtures.
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A beautiful new walk in shower installed with grab bars, shelves, a shower seat, and stylish black fixtures.

+9

Response time1 day
Response rate99%
41 neighbors recently requested a quote
Avatar for Roofing Solutions
Roofing Solutions
4.5(
6
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2019

Free estimates

Emergency services offered

"Have been working with Roofing solutions for a couple of years on multiple projects. Every project has been finished quickly and smoothly."
What We Do...
What We Do...
What We Do...
What We Do...
What We Do...

+64

Response time5 hrs
Response rate97%
13 neighbors recently requested a quote
Avatar for New Castle Constructs, LLC
New Castle Constructs, LLC
4.9(
31
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2023

Free estimates

Credit card accepted

New Castle Constructs is 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.

Roof Replacement
Roof Replacement
Roof Replacement
2 neighbors recently requested a quote
Recommended by83%of homeowners
AML Top Quality Construction
4.6(
27
)

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 2009

Free estimates

Emergency services offered

"Casey and his crew have been my go-to team over the last 10years and on several projects, from complete rehabs from roofing. soffits and fascia, outside, to the new kitchen and baths inside! My wife especially LOVES the screened -in porch they added on to our family home, and she's fussy about the quality of work to say the least. They have traveled far and wide across the Eastern Shore and even rehabbed a rental for me in Dover! Good work is hard to find nowadays, but Casey and crew clean up after themselves daily, and most importantly are REASONABLE in their rates !"
Response time1 day
6 neighbors recently requested a quote
Recommended by70%of homeowners
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Roofing questions, answered by experts

The easiest way to tell if your roof vent boot is leaking is to look in your attic for signs of water damage. You might see visible moisture, water spots, or mold on the roof decking around the roof vent or damaged or soggy insulation below it. If you don’t have access to your attic or aren’t sure if the vent boot is the issue, hire a professional to come inspect your roof and figure out the underlying issue.

The most common roof pitch is 4:12, which means a rise of 4 inches for every 12 inches of horizontal run. However, roof pitch varies widely based on roof design, climate, and even the roofing materials you plan to install. Your building type also plays a role, as flat roofs are common on commercial buildings and some modern homes.

Always inform your insurance company when you get a new roof. A new roof may entitle you to lower rates or discounts, and if you need to make a claim, they’ll have up-to-date information on your roof. You’ll need to provide documentation—ask your insurance agent what you need to submit to prove you had your roof replaced.

Yes, materials like cool roofs and solar shingles may be considered.

Copper roofs last an average of around 100 years, making it one of the longest-lasting types of roofs. It’s significantly more expensive than an asphalt shingle roof, but it also lasts three to four times as long, providing great value for the money. You can extend the life of your copper roof by carrying out routine maintenance, like scheduling annual cleaning and roof inspections.

The Chestertown, MD homeowners’ guide to roofing services

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