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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

"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."
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%
40 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
3 neighbors recently requested a quote
Recommended by83%of homeowners
AML Top Quality Construction
4.6(
27
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair

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
6 neighbors recently requested a quote
Recommended by70%of homeowners
Avatar for Complete Exteriors, LLC
Complete Exteriors, LLC
4.6(
68
)
Asphalt Shingle Roofing - Install or ReplaceWood Shake or Composite Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For Business+1 more

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 1999

Free estimates

Warranties offered

"Mike came out promptly to inspect the roof and give us an estimate. He was very professional and answered all our questions. The crew was very hardworking and finished the job in one day despite having to hand carry all the materials up to the roof. They did a terrific job with cleanup too. Roof looks great!. I would highly recommend Complete Exteriors for anyone needing a new roof."
Shingle Replacement
Shingle Replacement
Shingle Replacement
Shingle Replacement
Shingle Replacement

+10

Response time1 day
Response rate94%
47 neighbors recently requested a quote
Avatar for Canales Service, LLC
Canales Service, LLC
4.7(
117
)
Asphalt Shingle Roofing - RepairNatural Slate 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%
110 neighbors recently requested a quote
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Showing 1-10 of 292
Roofing questions, answered by experts

How long shingles last depends on the type of shingles you have on your roof. Asphalt shingles normally last anywhere from 15 to 30 years, metal shingles can last anywhere from 15 to 100 years, and tile shingles can last anywhere from 50 to 100 years or more.

You can walk on a TPO roof, but you should only do so when necessary and wear footwear that’s less likely to puncture the surface. If you anticipate needing to frequently walk on your TPO roof, reinforce walkways to protect against punctures. TPO roofing can also be slippery, so in most cases, you’ll want to leave walking on it to the pros.

Fall is widely considered the best time of year to replace a roof. The moderate temperatures are ideal for roofing crews to work and for new shingles to seal properly. Additionally, autumn weather is often drier, reducing the risk of weather-related delays compared to the rainier spring season.

While spring is also a viable option, the higher chance of rainfall can slow down the project. The main drawback to a fall installation is that it's the peak season for roofers, which can lead to higher prices and scheduling challenges.

To potentially save money, you could consider scheduling your roof replacement during the summer or winter off-seasons. However, both seasons have significant disadvantages. Extreme summer heat can make shingles too soft to handle, while winter's cold, snow, and ice can create dangerous working conditions and prevent shingles from sealing correctly, as they typically require temperatures above 40-45°F.

There are several signs that indicate you’ll need new underlayment. Clear signs include missing or damaged roofing and exposing the underlayment to the elements. Additionally, if you notice water damage in your home by the roof after a storm, it could indicate that your underlayment may need to be replaced. If your gutters aren’t draining properly, it could also lead to rotting or water damage to the underlayment.

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.

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.