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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 Power Home Remodeling
Power Home Remodeling
4.3(
885
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Repair - For Business+19 more

Serving Chestertown, MD and surrounding areas

Approved (Corporate)

Super Service Award Winner

In business since 1992

Free estimates

Warranties offered

"We are having our roof and gutters replaced currently and have had a great experience so far! From the sales intro w/ Christian, to the crew doing the work, and QA follow-up w/ Alex, all of the steps have gone smoothly and the staff has been very knowledgeable and helpful."
Fresh Curb Appeal
Full Home Remodel - Siding, Windows, and Gutters
Fresh Curb Appeal
Full Home Remodel - Siding, Windows, and Gutters
Fresh Curb Appeal

+31

37 neighbors recently requested a quote
Recommended by92%of homeowners
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%
50 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
4 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
5 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 - RepairNatural Slate Roofing - Repair+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%
108 neighbors recently requested a quote
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Roofing questions, answered by experts

Re-roofing is the process of placing a layer of shingles over top of existing shingles, rather than pulling out those shingles and replacing them. Compared to a full roof replacement, re-roofing typically costs less and requires less labor and time. It's not an option for everyone, though. You may need a full roof replacement if your roof already has more than one layer of shingles. A full replacement may also be necessary if your roof has extensive damage.

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.

A square of shingles covers 100 square feet and usually ranges from 150 to 240 pounds. It all depends on the material and type of shingle.

A well-maintained tile roof can last anywhere from 40 to over 100 years, with its exact lifespan depending on the material and level of care. Proper maintenance, which includes keeping the roof clean, free of debris, and performing routine repairs for any cracked tiles, is crucial for longevity. The lifespan varies significantly by tile type:

  • Clay, terracotta, and slate tiles are highly durable and can last over 100 years.

  • Concrete tiles typically last from 30 to 100 years.

  • Metal tile roofs generally last between 40 and 70 years.

  • Composite tile roofs have a lifespan of 20 to 50 years.

Be aware that maintenance for a tile roof can sometimes be more expensive than for an asphalt roof.

Building an A-frame roof falls under the category of constructing a steep roof. While its structure is relatively simple, its height and requirements for more materials than a shallow roof design can increase its cost significantly. Expect prices for building an A-frame roof to hover around average to slightly above average.

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.