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TRUSTED BY CHESTERTOWN, MD HOMEOWNERS

  • Average homeowner rating star icon4.5
    Average homeowner rating
  • Verified reviews icon125
    Verified roofing services reviews

Find Roofers in Chestertown

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 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."
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 rate100%
47 neighbors recently requested a quote
Avatar for New Castle Constructs, LLC
New Castle Constructs, LLC
4.9(
31
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Repair - For BusinessFlat, Foam or Single Ply Roofing - Repair+2 more

Serving Chestertown, MD and surrounding areas

Approved

In business since 2023

Free estimates

Credit card accepted

New Castle Constructs is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers' interests, and make their concerns the basis of our business.

Roof Replacement
Roof Replacement
Roof Replacement
5 neighbors recently requested a quote
Recommended by83%of homeowners
AML Top Quality Construction
4.6(
27
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Install or Replace

Serving Chestertown, 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 Canales Service, LLC
Canales Service, LLC
4.7(
117
)
Asphalt Shingle Roofing - RepairMetal Roofing - RepairAsphalt Shingle Roofing - Install or Replace - For Business+8 more

Serving Chestertown, 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 rate86%
104 neighbors recently requested a quote
Avatar for Economy Restoration, LLC
Economy Restoration, LLC
4.1(
28
)
Asphalt Shingle Roofing - RepairMetal Roofing - RepairMetal Roofing - Repair - For Business+7 more

Serving Chestertown, 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%
19 neighbors recently requested a quote
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Showing 1-10 of 290
Roofing questions, answered by experts

Here are a few tips on how to choose a roofer:

  • Get everything in writing

  • Ask for insurance, license, and bond, then verify them

  • Check their reviews 

  • Ask for recommendations

  • Get multiple quotes

You’ll also want to watch out for any red flags like:

  • Pushy sales tactics

  • Not willing to show necessary documentation

  • Bad gut instincts

The best material to sheath a roof will depend on your budget and if you require the strength of more robust materials. For most homes, the added strength is unnecessary, and oriented strand board, or OSB, makes sense. It’s inexpensive and robust enough for most roof types. Another popular but slightly more expensive option is plywood.

Shingle roofing can last anywhere from 15 to 50 years, depending on the type and quality of shingle, your local climate, and how well you maintain your roof. If you live in an area that sees extreme weather, like strong winds, hail storms, or hurricanes, the average life span of a shingle roof will often be on the shorter end, especially if you choose a more affordable roof shingle that isn’t designed to persist through extreme weather.

Gable vents are more common in older homes built before the 1970s. Homes built after this era use ridge vents or soffits, but you can sometimes find homes with both gable and ridge vents. Gable vents can have a purely aesthetic purpose, while ridge vents hide in the roof shingles so air can flow under the roof while keeping the attic dry.

Using an ice and water shield underlayment under a metal roof is a good way to protect the roof and your home from damage in colder climates that see a lot of winter weather. Traditional underlayment isn’t effective underneath a metal roof, though, so be sure to install one specifically made for metal roofs to get the best protection.

The Chestertown, MD homeowners’ guide to roofing services

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