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TRUSTED BY CHESTER, MD HOMEOWNERS

  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon672
    Verified roofing services reviews

Find Roofers in Chester

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

Serving Chester, 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."
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+45

Response time1 day
Response rate86%
3 neighbors recently requested a quote
Avatar for Roofing Pups, Roofing & Siding
Roofing Pups, Roofing & Siding
4.7(
64
)

Serving Chester, MD and surrounding areas

Approved

Super Service Award Winner

In business since 1994

Free estimates

Credit card accepted

"There's nothing worse that dealing with pooring rain and strong winds and then hearing the drip, drip sound of water coming into your home due to a damaged roof. I reached out to roofing repair companies through Angie's list and Roofing Pups responded. Marcus came out the next day and put my fears at ease. The bad news was that I needed a new roof. He showed me my options available, categorized as "good", "better" and "best". Despite my choosing the lowest option, he still threw in some discounts and upgrades at no additional cost. I signed the contract and he arranged for someone to come out at tarp my roof. He even went the extra mile of going to Home Depot and setting up buckets in my attic to catch the water still coming in. The roofing crew came out two days later and gave me a beautiful new roof. They then meticulously cleaned the area. It was great working with Roofing Pups. I couldn't be happier and highly recommend!"
Roof Install
ROOFING PUPS
ROOFING PUPS
ROOFING PUPS
PROJECTS

+4

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

Serving Chester, 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%
40 neighbors recently requested a quote
Avatar for Roofing Solutions
Roofing Solutions
4.5(
6
)

Serving Chester, 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%
14 neighbors recently requested a quote
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

At JDH Remodeling, we specialize in enhancing and protecting your home with a comprehensive range of services. As expert roofing contractors, we ensure your roof is robust and reliable. Our gutter services are designed to effectively manage water flow, preventing damage to your home. We also offer siding solutions that not only add aesthetic appeal but also provide essential protection against the elements. Our insulation services improve energy efficiency, enhancing comfort and reducing costs. Additionally, our window installation services bring natural light and style into your home while ensuring durability and performance. Trust JDH Remodeling for quality craftsmanship and exceptional service.

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+36

Response time6 hrs
2 neighbors recently requested a quote
Recommended by54%of homeowners
AML Top Quality Construction
4.6(
27
)

Serving Chester, 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
Avatar for Canales Service, LLC
Canales Service, LLC
4.7(
117
)

Serving Chester, MD and surrounding areas

Approved

In business since 2018

Free estimates

Credit card accepted

"I am a commercial contractor, and I had a roof emergency which turned into a nightmare,! These guys are great, dependability, integrity, trustworthy, and above all Great workmanship and professionalism. Cannot say enough about Eric, he is a great guy and does what he says and keeps his standards high. I will definitely use them again for other projects and recommend them to anyone looking to cut to the chase and hire a professional contractor at an affordable price."
New Roof Installation
New Roof Installation
New Roof Installation
Roofing project
Roof replacement

+12

Response time1 day
Response rate85%
114 neighbors recently requested a quote
Avatar for AJB Contractors LLC
AJB Contractors LLC
5.0(
9
)

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%
6 neighbors recently requested a quote
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Roofing questions, answered by experts

Stripping existing shingles and installing a new shingle roof takes a professional one to two days, and sometimes up to three days for larger roofs. Additional safety measures necessary for steep roofs can extend the timeframe even further, as do added measures, like replacing roof decking or reinforcing your roof structure to support heavier materials like slate or clay.

After you've chosen the best roofer for you, schedule an inspection and review the final contract. Your roofing company should be able to provide options for scheduling the work and a potential timeline for obtaining the permits and starting the job. Remember to always request everything in writing before work begins.

If you’re building the roof trusses yourself, which isn’t recommended, it will be more affordable than buying pre-built trusses. Trusses cost more because they use the same amount of material, but you’ll also be paying for the labor, as well as the delivery to your home. However, if you’re having a contractor build the roof for you, then trusses will be less expensive, as the labor costs to build roof framing on-site will cost more.

Using a staple gun to hang Christmas lights on your roof or shingles is not recommended. Puncturing your roof with staples can cause damage, leading to cracks, leaks, and exposure to the elements. Staples are also less reliable than other methods like roof clips. For a safer alternative that won't damage your roof, use shingle tabs.

Just like when you’re shingling a roof, you can install felt underlayment under a metal roof, but a synthetic underlayment like adhered ice and water shield is the best option. These use adhesives rather than mechanical fasteners, so you have fewer penetrations going through your roof deck and a lower risk of leaks. Ice and water shield is also easier to install because you don’t need additional tools or fasteners to attach it to the roof deck.

The Chester, MD homeowners’ guide to roofing services

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