Top-rated roofers.

Get matched with top roofers in Chester, MD

Enter your zip and get matched with up to 5 pros

Need a pro for your roofing project in Chester, MD?

Select your specific project to find the pro for you.

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 Roofing Pups, Roofing & Siding
Roofing Pups, Roofing & Siding
4.7(
64
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair

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%
415 neighbors recently requested a quote
Avatar for Spicer Bros. Construction Inc.
Spicer Bros. Construction Inc.
4.6(
78
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairMetal Roofing - Install or Replace+26 more

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."
Additional Photos
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%
40 neighbors recently requested a quote
Avatar for JDH Remodeling
JDH Remodeling
5.0(
11
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair+26 more

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.

Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+36

Response time6 hrs
2 neighbors recently requested a quote
Recommended by54%of homeowners
AML Top Quality Construction
4.6(
27
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair

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
)
Asphalt Shingle Roofing - RepairMetal Roofing - Install or Replace - For BusinessNatural Slate Roofing - Repair+8 more

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
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For Business

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
...
Showing 1-10 of 291
Roofing questions, answered by experts

If you’re looking for a cost-effective alternative to a traditional chimney, consider having a dummy chimney installed. Dummy chimneys can either be aesthetic-only or fully functional and can be installed on both new and older homes. Whether installed to match your neighborhood’s aesthetic or to vent your chimney, dummy chimneys are made out of a Glass-Reinforced Plastic (GRP) core, then covered with brick or stone slips to look like a traditional chimney.

Properly maintained roof decking can last between 20 and 30 years on average, though it varies based on a few factors. Mainly, the quality of roof decking materials and environmental conditions have the most impact on longevity. You can extend its lifespan by regularly inspecting your roof and making repairs as necessary.

When it comes to choosing the best roof color for a blue exterior, you have plenty of options. For a classic neutral look, go with a light gray, dark gray, or black roof. Blend gray tones if you want a more eye-catching look for your roof, or go for a different splash of color with a green or even red. Take inspiration from your neighbors if you want your house to fit in on the block.

You can damage your shingles if you use the wrong type of paint on them. You should always use acrylic latex paint specifically formulated for shingles. Other types of paint may trap moisture, which can cause bigger problems like rot and mildew. Considering that roof replacement costs $9,100 on average, it’s definitely best to avoid making this mistake.

Besides using the right paint, remember that painting your shingles will require increased maintenance.

The average cost to winterize a house is about $250, but it can range from $65 to $1,000 depending on the type of work that needs to be done. For homeowners that are experienced DIYers, it can save quite a bit on costs. However, you shouldn’t attempt tasks you aren’t familiar with or are potentially dangerous.

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.