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Find Asphalt shingle roofing installers and replacers in Chestertown

Avatar for CHESAPEAKE ROOFING WINDOWS & SIDING
CHESAPEAKE ROOFING WINDOWS & SIDING
4.9(
97
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 1987

Free estimates

Warranties offered

"David and his window installation team are incredibly hard working and professional. They have a strong commitment to excellence and work diligently to ensure everything is done well. David answers questions and explains options thoroughly. We would definitely do business with Chesapeake Roofing in the future based on our experience."
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+45

Response time1 day
Response rate86%
3 neighbors recently requested a quote
Avatar for Tar Heel Construction Group, LLC
Tar Heel Construction Group, LLC
5.0(
69
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2004

Free estimates

Customers say: Quality work

"Courteous and professional recent roof and gutter replacement. Thorough presentation of product by Brian, hard working crew, and good supervision of task from beginning to completion by Ryan and Brian. Attention given to each of my questions and concerns. Good phone communication for time schedules, arrivals, changes, etc."
Overview of roof
Front view of roof
Response time11 hrs
Response rate95%
7 neighbors recently requested a quote
Avatar for Spicer Bros. Construction Inc.
Spicer Bros. Construction Inc.
4.9(
64
)

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%
38 neighbors recently requested a quote
Avatar for AJB Contractors LLC
AJB Contractors LLC
5.0(
8
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2025

Free estimates

Credit card accepted

"AJB Contractors contacted, quoted a price, and emailed the contract for to sign. The next day my roof was repaired. I will definitely use this company for any future home projects. Danny was the point of contact, he was great. "
Response time4 hrs
Response rate99%
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FAQs for asphalt shingle roofing installation and replacement projects in Chestertown, MD

Roofing professionals can usually install a medium-sized asphalt shingle roof in two to three days. Installation time increases if your roof is particularly steep or difficult to access or has features like chimneys or skylights that roofers must work around.

Three-tab asphalt shingles usually have the lowest upfront cost of any roofing shingle material. They’re sturdy and typically last 15 to 20 years. However, they may have a shorter lifespan in especially hot or cold climates. Talk to a local roofing professional about the best materials for your climate. In some cases, materials with a higher upfront cost may save you more on repairs or replacements in the long run.

Start by multiplying the length by the width of your roof to calculate the square footage. Most shingle replacement costs $4 to $12 per square foot for materials and labor, depending on factors like the material and the slope of your roof. Once you know the size of your roof, you can calculate a rough estimate of total costs or contact a local roofing professional to provide you with a custom quote.

Asphalt shingles are generally considered to be a low-maintenance item. However, cleaning your asphalt roofing can help prolong the lifespan and keep it looking fresh. If you’re comfortable with DIY and have the proper equipment, you may be able to clean your asphalt shingles yourself. However, if you have an especially high or steep roof, it’s usually safer to hire a professional roof cleaner.

The Chestertown, MD homeowners’ guide to asphalt shingle roofing installations and replacements

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