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Find Asphalt shingle roofing installers and replacers in Chester

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

Serving Chester, MD and surrounding areas

Approved

In business since 1987

Free estimates

Warranties offered

"Chesapeake Roofing provided an all-around great service. They were pretty quick to get back to me when I inquired about an estimate and they were quick to set up a date to come out and give me a quote. Their pricing was about on par with other quotes I had received and they were able to set up a date for the replacement a week after I received the estimate. The day of the job, they were out there early and were done just after noon. They did a fairly decent job cleaning up, although they did miss a couple of nails and shingles. This was my first experience having a roof replaced and I'm very satisfied with the work that Chesapeake Roofing did."
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+45

Response time1 day
Response rate86%
5 neighbors recently requested a quote
Avatar for Roofing Pups, Roofing & Siding
Roofing Pups, Roofing & Siding
4.9(
51
)

Serving Chester, MD and surrounding areas

Approved

Super Service Award Winner

In business since 1994

Free estimates

Credit card accepted

"I needed a new roof and wanted gutters and gutter covers. After meeting with one other company, I selected Roofing Pups. Shawn of Roofing Pups was friendly, mannerly, professional, and knowledgeable. He offered a much better deal that included everything I wanted, at a reasonable price. Whenever I called Shawn or his colleague, they responded by text or phone within seconds. The project was completed in three days, and cleanup was done daily. All staff and workers were friendly, professional, and well-versed in their skills. The workmanship was superb! After the work was completed, it rained hard the next day. There were no leaks, rain was flowing away from my home as it should, and the appearance of my house looks great. Overall, I’m a happy customer and would recommend Roofing Pups to friends and family. "
Roof Install
ROOFING PUPS
ROOFING PUPS
ROOFING PUPS
PROJECTS

+4

Response time1 day
Response rate93%
700 neighbors recently requested a quote
Avatar for Home Genius Exteriors
Home Genius Exteriors
4.9(
358
)

Serving Chester, MD and surrounding areas

Approved

Super Service Award Winner

In business since 2004

Free estimates

Emergency services offered

"Had our roof replaced, looks like a clean install. Trey was easy to talk to and was very assuring. We'll see how the roof holds up against this weekend's snowstorm or whatever's coming our way. Yes I copy pasted my own review from Google Reviews."
Roofing
Roofing
Roofing
Roofing
Roofing

+85

1490 neighbors recently requested a quote
Recommended by96%of homeowners
Avatar for Power Home Remodeling
Power Home Remodeling
4.8(
697
)

Serving Chester, 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

36 neighbors recently requested a quote
Recommended by92%of homeowners
Avatar for JDH Remodeling
JDH Remodeling
5.0(
11
)

Serving Chester, MD and surrounding areas

Approved

In business since 2009

Free estimates

Emergency services offered

"The entire process went very well. The team at JDH is excellent, from their sales guys, to on site managers, to individual workers. All are professional and courteous and take their time to do it right. We've had a few scheduling hic-ups throughout the process, but overall they've been excellent from start to finish. Most importantly, my new roof and skylights look top notch, and will last a lifetime!"
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+36

Response time6 hrs
4 neighbors recently requested a quote
Recommended by54%of homeowners
Avatar for Riptide Remodeling LLC
Riptide Remodeling LLC
5.0(
18
)

Serving Chester, MD and surrounding areas

Approved (Corporate)

Super Service Award Winner

In business since 2010

Free estimates

Warranties offered

"One of the company owners (Rich) came and gave us an estimate for roof replacement that was very fair, compared to an estimate we had received from a prominent national company. Rich was pleasant, honest and straightforward, very easy to work with. The work was done when he promised it would be and we are very happy with the finished product. I would not hesitate to recommend this company, Riptide Remodeling, to anyone looking to replace their roof. They also replaced our shutters very nicely."
Front View
Right Side
Left Side
Back
Back 2

+24

Response time12 hrs
Response rate94%
29 neighbors recently requested a quote
Avatar for Spicer Bros. Construction Inc.
Spicer Bros. Construction Inc.
4.9(
64
)

Serving Chester, MD and surrounding areas

Approved

In business since 2002

Free estimates

Warranties offered

"From beginning to the very end, AWESOME! On time for the estimate and on time for the scheduled installation day. Every membership the staff was friendly, knowledgeable, patient with all with questions. The roof replacement was done quickly and cleanup was thorough. We are very happy."
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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 Chester, 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%
1 neighbors recently requested a quote
AML Top Quality Construction
4.8(
23
)

Serving Chester, 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
7 neighbors recently requested a quote
Recommended by73%of homeowners
Showing 1-10 of 16
FAQs for asphalt shingle roofing installation and replacement projects in Chester, 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 Chester, 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.