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TRUSTED BY CHESTER, MD HOMEOWNERS

  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon720
    Verified roofing services reviews

Top-Rated Roofers in Chester - Updated Nov 2026

Avatar for Roofing Pups, Roofing & Siding
Roofing Pups, Roofing & Siding
4.7(
75
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair+1 more

Serving Chester, MD and surrounding areas

Approved (Corporate)

Super Service Award Winner

In business since 1994

Free estimates

Credit card accepted

"We had a really good experience with Roofing Pups. Their rep Alex was great to work with, and the roofing crew that came to our house did a good job and cleaned up afterward. We opted to get our gutters replaced as well as our roof, which required a second day of work. The Roofing Pups employee in charge of this job (also named Alex) noticed that the color of the new gutters didnt match our house, and made a point of checking it with us before getting started. We really appreciated this as the new gutters would have clashed with the color of our siding! Everyone with the company was great about making the change, ordering new parts and rescheduling the job. We were very impressed with their service and professionalism. We would definitely use Roofing Pups again!"
Roof Install
ROOFING PUPS
ROOFING PUPS
ROOFING PUPS
PROJECTS

+4

Response time1 day
Response rate93%
169 neighbors recently requested a quote
Avatar for Home Genius Exteriors
Home Genius Exteriors
4.9(
388
)
Asphalt Shingle Roofing - Install or Replace

Serving Chester, MD and surrounding areas

Approved

In business since 2004

Free estimates

Emergency services offered

Elevate your home with Home Genius Exteriors, setting the standard by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It?s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!

Asphalt Roofing
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing

+76

288 neighbors recently requested a quote
Recommended by96%of homeowners
AML Top Quality Construction
4.6(
27
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Install or Replace

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 time2 days
4 neighbors recently requested a quote
Recommended by70%of homeowners
Avatar for Economy Restoration, LLC DBA Economy Roofing & Restoration
Economy Restoration, LLC DBA Economy Roofing & Restoration
4.3(
35
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Repair - For Business

Serving Chester, MD and surrounding areas

Approved

In business since 2018

Free estimates

Emergency services offered

"Jordan Taylor was our rep and did an outstanding of explaining the entire process to us, including how to submit the roof replacement to insurance due to a wind storm. He was super responsive for every question, and he personally got our HOA approval, then walked it through the town govt to get the permit! On the day of installation, his team worked efficiently and quickly, and our roof was completed by late afternoon, including full and thorough cleanup. Jordan came back the next day to walk the property to make sure all garbage was picked up. Economy Restoration will also provide a Quality Control person to go up on the roof for the final inspection, which really gives us a secure feeling. Our roof is amazing, along with the entire process and the pricing is very fair. I highly recommend Jordan and Economy Restoration!"
Roof Replacement During Install
Finished Product
Chimney Flashing
Chimney & Step Flashing
Rear Elevation Finished Product

+3

Response time1 day
Response rate90%
97 neighbors recently requested a quote
Avatar for Riptide Remodeling LLC
Riptide Remodeling LLC
5.0(
30
)
Asphalt Shingle Roofing - Install or Replace

Serving Chester, MD and surrounding areas

Approved (Corporate)

Super Service Award Winner

In business since 2010

Free estimates

Credit card accepted

"Rich and Mike at Riptide remodeling were the pinnacle of professionalism. They provided topnotch communication throughout the entire process of having a new roofing system installed on my home. This came at an exceptional bargin while still receiving top of the line product. If you have roofing or any remodeling needs, you would be foolish to not use riptide as your contractor of choice."
Front View
Right Side
Left Side
Back
Back 2

+24

Response time12 hrs
Response rate100%
11 neighbors recently requested a quote
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Roofing FAQs, answered by experts

The cost to replace a roof typically ranges from $8,700 to $22,000, with a national average of around $9,200. The total cost depends on the size of your roof and whether you need a full replacement or can simply place new shingles over the old ones. A full replacement, which is necessary if the roof is several decades old or has multiple layers, is more expensive. This process involves tearing off the old roofing materials, inspecting and repairing the underlying structure, and then installing the new roof.

A roof overlay will last an average of 15 years, compared to the 20 to 30 years or more that a full roof replacement for a shingle roof will last. An overlay’s lifespan may be shortened even further if there’s underlying damage to the existing roof or structural problems with the roof supports.

Homeowners insurance sometimes covers roof decking, but it depends on the cause of damage and whether the decking was properly installed. If the roof decking was damaged by a severe storm, then it will likely be covered. Insurance may also pay for roof decking work if building codes require it. However, insurance won’t cover damage caused by normal wear and tear or poor maintenance practices.

Asphalt roofs provide better insulation than metal roofs, but that doesn’t always mean that asphalt roofs are better for reducing heating and cooling bills. In hotter climates, metal roofs will usually be better for home efficiency because the material reflects more sunlight and reduces solar heat gain. In colder climates, asphalt roofs are sometimes superior in terms of efficiency because they introduce more solar heat gain to your home and have greater insulating capabilities. However, metal roofs installed with an air gap can provide similar levels of insulation.

Homeowners insurance does not usually cover roof soft spot repair. Since this damage is usually caused by wear and tear and often found on aging roofs, your insurance claim will likely be rejected. If a soft spot develops due to damage from a storm, repairs may be covered, but in general, expect to pay out of pocket for soft spot repairs.

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.