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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

Verified Reviews for Roofing pros in Chestertown, MD

*The Angi rating for Roofing companies in Chestertown, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Roofing needs.

*The HomeAdvisor rating for Roofing companies in Chestertown, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Roofing needs.

Last update on July 04, 2025

Find Roofers in Chestertown

Avatar for Roofing Pups, Roofing & Siding
Roofing Pups, Roofing & Siding
4.7(
67
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair

Serving Chestertown, MD and surrounding areas

Approved (Corporate)

Super Service Award Winner

In business since 1994

Free estimates

Credit card accepted

"Informative and friendly first meeting, complete with detailed photos of the entire roof and an explanation of the process, followed by 1-day installation of a new roof, with excellent workmanship and a hardworking crew."
Roof Install
ROOFING PUPS
ROOFING PUPS
ROOFING PUPS
PROJECTS

+4

Response time1 day
Response rate93%
217 neighbors recently requested a quote
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Avatar for Home Genius Exteriors
Home Genius Exteriors
4.9(
1,212
)
Asphalt Shingle Roofing - RepairInspection - RoofingFlat, Foam or Single Ply Roofing - Repair+4 more

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 2004

Free estimates

Emergency services offered

"The staff at Home Genius were very knowledgeable and friendly. Our roof was installed sooner than expected and looks amazing. Best looking roof on our street! Definitely recommend Home Genius if you’re in need of a new roof."
WINDOWS
WINDOWS
WINDOWS
WINDOWS
SIDING

+73

Response time4 hrs
Response rate93%
2727 neighbors recently requested a quote
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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

"Excellent!!! Great work !!! They have done 2 big jobs for us (roof & windows); we were happy with both results."
Fresh Curb Appeal
Full Home Remodel - Siding, Windows, and Gutters
Fresh Curb Appeal
Full Home Remodel - Siding, Windows, and Gutters
Fresh Curb Appeal

+31

36 neighbors recently requested a quote
Recommended by92%of homeowners
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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

"The roof was replaced and looks great. The crew was very prompt, did a great job, and left a very clean work site."
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
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Avatar for Roofing Solutions
Roofing Solutions
4.5(
6
)
Asphalt Shingle Roofing - Install or Replace - For BusinessFlat, Foam or Single Ply Roofing - Repair- For BusinessFlat, Foam, or Single Ply Roofing - Install or Replace- For Business+8 more

Serving Chestertown, MD and surrounding areas

Approved

In business since 2019

Free estimates

Emergency services offered

"Have been working with Roofing solutions for a couple of years on multiple projects. Every project has been finished quickly and smoothly."
What We Do...
What We Do...
What We Do...
What We Do...
What We Do...

+64

Response time5 hrs
Response rate98%
11 neighbors recently requested a quote
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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
Request Quote
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
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Avatar for Complete Exteriors, LLC
Complete Exteriors, LLC
4.6(
68
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessWood Shake or Composite Roofing - Install or Replace+1 more

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 1999

Free estimates

Warranties offered

"The price on the roof was very competitive and the work was completed on time. The quality of the work was excellent."
Shingle Replacement
Shingle Replacement
Shingle Replacement
Shingle Replacement
Shingle Replacement

+10

Response time1 day
Response rate94%
54 neighbors recently requested a quote
Request Quote
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

"The crew showed up on time, worked quietly and efficiently and left the area better than it was. Our new roof is beautiful and expertly installed. Erick is fair and honest . Pricing was competitive. I would trust him with any other work I might need."
New Roof Installation
New Roof Installation
New Roof Installation
Roofing project
Roof replacement

+12

Response time1 day
Response rate86%
109 neighbors recently requested a quote
Request Quote
Avatar for East Coast Roofing Systems, LLC
East Coast Roofing Systems, LLC
4.1(
7
)
Asphalt Shingle Roofing - Install or Replace - For BusinessFlat, Foam, or Single Ply Roofing - Install or ReplaceFlat, Foam, or Single Ply Roofing - Install or Replace- For Business+4 more

Serving Chestertown, MD and surrounding areas

Approved

In business since 2021

Free estimates

Emergency services offered

"They were very nice and stood behind a free inspection of my roof. I would call them again if I have any future needs."
Birdseye Before
Home Frontage Before
Birdseye After
Home Frontage After
Home Side After

+32

Response time8 hrs
Response rate91%
Recommended by83%of homeowners
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Showing 1-10 of 291
Roofing questions, answered by experts

Cool roofs last for roughly 15 to 30 years. You can install a cool roof coating over an existing roof, but keep in mind that this might not be worth it if your roof is near the end of its life expectancy. If your roof isn’t near the end of its life, adding a cool roof coating can make your existing roof more energy-efficient and help it last longer, so you’ll have to weigh the pros and cons.

You can put new shingles over old shingles, but most municipalities only allow for two layers of shingles before you have to rip off the old roof and start fresh. In some areas, only a single layer of shingles is allowed due to the weight a bundle of shingles adds to your structure. In most cases, it’s a good idea to remove your old shingles before you install new shingles, especially if you suspect that a roof leak may have compromised the decking underneath.

A roof replacement will usually include removal of your old roof, shingle replacement, and a new roof underlayment, but it may only include adding new shingles if you’re layering new shingles over the old shingles. If you have signs of roof leaks or your roofer finds water damage to the roof decking underneath your old roof, it can also include replacement of the OSB or plywood decking that lays over your rafters and supports the roofing material above.

If a home isn’t properly winterized, the pipes can freeze and burst, causing flooding and massive property damage. It can also leave your house susceptible to pests, which can infest it and cause significant damage. Winterizing a home can prevent many potential issues and save you money on costly repairs.

Roofing replacements and repairs expose the interior of your home to the elements. Failing to protect these areas during inclement weather can cause extensive damage and job delays. Have a conversation with your pro to learn their plans to use tarps, plastic sheeting, or other waterproofing methods to keep your home safe. Also, ask whether your pro will inspect your home during rain or snow to ensure the covering works.

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.

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