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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(
106
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 1987

Free estimates

Warranties offered

"I was very happy with the roof replacement that Chesapeake Roofing recently did on my home in Heritage Harbour in Annapolis. The salesman/estimator was quick and thorough, and always gave fast responses to my questions. The installers did a great job, carefully tarping the flower beds and deck to protect them and making a thorough sweep for nails and debris when they were finished. I couldn't be happier with the end result, and won't hesitate to recommend Chesapeake Roofing to my friends and neighbors."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+45

Response time1 day
Response rate86%
4 neighbors recently requested a quote
Avatar for Tar Heel Construction Group, LLC
Tar Heel Construction Group, LLC
4.8(
82
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2004

Free estimates

Customers say: Quality work

"Unlike a couple of other business coordinators from competitors, Tar Heel Construction's coordinator, Brain, was not only courteous and approachable, but also patient and empathetic. He did not try to rush into pressured business dealings but, instead, spent quality time listening attentively to our needs and thoroughly inspecting our roof, before engaging us in a more informative discussion about our project. Brian was careful to solicit answers to questions that aligned with our goals, so that he could show and explain relevant options for us to choose from. His knowledge of our roofing problems, along with his unexaggerated estimates and forthrightness gained our trust and we decided to choose him and Tar Heel Construction for the first phase of our project, which was to repair our roof's "dead valley" area. Then, not long after signing the contract to repair the "dead valley," and just before the date scheduled to begin that work, we left Brian a message on a Saturday to report that rain had come in the house from the "dead valley" area of the roof. Brian contacted us immediately, even though he was at a soccer game with his son, and told us he would send a crew to our house within 24 hours! That extraordinary level of care persuaded us to not postpone getting the shingle part of the project done and we called Brian back to have him send us a new contract to include completing the work for both the "dead valley" and replacing the shingles on the entire roof. Within three days of signing the new contract, Brian sent two teams out to begin the work and we had a new complete roof, just before more rain! If you are looking to repair or replace your roof and want an unparalleled customer-focused experience, that consists of a hassle free consultation, a fair price and financing options with low interest rate, then call on Brian and Tar Heel Construction and get Peace of Mind from receiving outstanding workmanship and the state-of-the-art products."
Overview of roof
Front view of roof
Response time11 hrs
Response rate95%
8 neighbors recently requested a quote
Avatar for Roofing Pups, Roofing & Siding
Roofing Pups, Roofing & Siding
4.7(
61
)

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 1994

Free estimates

Credit card accepted

"Replaced a roof on storage shed, repair fascia and replaced gutters. The team was quick and professional. Everything was done in one day to my complete satisfaction."
Roof Install
ROOFING PUPS
ROOFING PUPS
ROOFING PUPS
PROJECTS

+4

Response time1 day
Response rate93%
611 neighbors recently requested a quote
Avatar for Power Home Remodeling
Power Home Remodeling
4.3(
884
)

Serving Chestertown, MD and surrounding areas

Approved (Corporate)

Super Service Award Winner

In business since 1992

Free estimates

Warranties offered

"The process up to the QA Inspection was excellent. People were friendly and knowledgeable. Austin was excellent at giving honest answers to all our questions. When I asked him one he couldn’t answer he didn’t try to BS his way through, he simply said he didn’t know and then proceeded to make calls until he got an answer. At the Pre-install inspection we were told the install crew would arrive between 8-10. The install crew chief was very surprised to hear that when he arrived at 7. The installation was also excellent. Done and dusted by 4PM. The QA inspection cost you an excellent rating. It was little more than a high pressure sales pitch to replace my aluminum siding with vinyl. I just spent $20K on a new roof and he pressured us to spend another $40K on something that doesn’t need to be replaced. Not cool. I would definitely recommend Power, but with a caveat on the QA inspection."
Fresh Curb Appeal
Full Home Remodel - Siding, Windows, and Gutters
Fresh Curb Appeal
Full Home Remodel - Siding, Windows, and Gutters
Fresh Curb Appeal

+31

33 neighbors recently requested a quote
Recommended by92%of homeowners
Avatar for Home Genius Exteriors
Home Genius Exteriors
4.9(
387
)

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 2004

Free estimates

Emergency services offered

"The young man that came to see my missing shingles on my roof, was professional, informed, and polite. The only issue was that the company does NOT conduct repair as I needed. The company only replaces the entire roof. I am glad he came and advised about replacing the roof if we decide to do that and decide that we can afford it. Right now I need to repair the missing shingles. and he/ his company can not help me."
Roofing
Roofing
Roofing
Roofing
Roofing

+85

1746 neighbors recently requested a quote
Recommended by96%of homeowners
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.
Additional Photos
Additional Photos
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 Complete Exteriors, LLC
Complete Exteriors, LLC
4.6(
68
)

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 1999

Free estimates

Warranties offered

"Complete Exteriors recently replaced the shingles on my townhouse in Gaithersburg, MD. I also hired them to replace our gutters and downspouts. The roof shingles are CertainTeed Landmark Pro architectural shingles and they look great. The Complete Exteriors crew arrived around 7 A.M. and they completed the job in less than one day (done before 3 P.M.). The crew supervisor kept me in the loop throughout the roof replacement process and frequently showed me close-up pictures of the work being done on the roof. Their price for the roofing work was excellent (I got eight bids, and their price was the best by far for the roofing job). The gutters and downspouts were replaced the next day. Complete Exteriors subcontracted this work to another vendor, which also did good work. In retrospect, I may have divided the contract into two jobs, solely because the price from Complete Exteriors was not the lowest bid I received for the gutters and downspouts. However, their overall combined price for both the roofing and the gutters and downspouts was at least $500 lower than any other bid I received. Another reason I gave them both contracts was to simplify the contracting process, as I wanted one company to be responsible for both the roofing and the gutters and downspouts. Overall, I am very satisfied with the work done by Complete Exteriors' roofing crew and by the subcontractor they hired that installed the new gutters and downspouts, and I highly recommend Complete Exteriors."
Shingle Replacement
Shingle Replacement
Shingle Replacement
Shingle Replacement
Shingle Replacement

+10

Response time1 day
Response rate93%
59 neighbors recently requested a quote
Avatar for AJB Contractors LLC
AJB Contractors LLC
5.0(
9
)

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%
2 neighbors recently requested a quote
Erie Home
4.4(
73
)

Serving Chestertown, MD and surrounding areas

Approved (Corporate)

In business since 1976

Free estimates

Credit card accepted

With over 40 years of experience in home remodeling and satisfied customers in over 30 states, you can rest assured knowing that Erie Home delivers the best value and service to our customers. Recognized as one of the top remodelers in America, Erie Home is licensed, bonded, insured, and guarantees all of our work.\n\nOur service starts with a professional on-site evaluation and inspection. During this free inspection, we will measure the roof, provide samples (both metal and asphalt options), and discuss the roofing process in detail with the customer.\n\nOur stone coated metal roofing system offers upscale styles to enhance your home's appearance and won't break, burn, curl, split, rot, or grow mold! With a limited lifetime warranty, you will love our modern-looking metal roofing options! Erie's proven commitment to delivering the absolute best value and service to our customers differentiates us from the competition. Contact us today and let us help you find your forever roof!\n\n

8 neighbors recently requested a quote
Recommended by92%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

"THE ROOF WAS REPLACED QUICKLY AND EFFICIENTLY WITH NO WASTE OF MATERIAL OR TIME. THE CLEAN-UP WAS TOTAL AND THEY LEFT ME NOTHING TO DO BUT ENJOY MY HARBOR BLUE ROOF. I HAVE RECEIVED MANY COMPLIMENTS. ONE SUGGESTION IS: SIGNAGE FOR AML WAS NOT PUT ON THE LAWN. THANK YOU CASEY AND YOUR PLEASANT WORKMEN."
Response time1 day
8 neighbors recently requested a quote
Recommended by70%of homeowners
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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.