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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 CHESAPEAKE ROOFING WINDOWS & SIDING
CHESAPEAKE ROOFING WINDOWS & SIDING
4.9(
106
)
Asphalt Shingle Roofing - RepairMetal Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace+26 more

Serving Chestertown, MD and surrounding areas

Approved

In business since 1987

Free estimates

Warranties offered

"I am extremely satisfied with the product and services. The installation was efficient and properly done. I have used this company before for roofing and trust their work."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+45

Response time1 day
Response rate100%
4 neighbors recently requested a quote
Request Quote
Avatar for Roofing Pups, Roofing & Siding
Roofing Pups, Roofing & Siding
4.7(
66
)
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%
266 neighbors recently requested a quote
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Avatar for Home Genius Exteriors
Home Genius Exteriors
4.9(
1,182
)
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%
2496 neighbors recently requested a quote
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Avatar for Power Home Remodeling
Power Home Remodeling
4.3(
885
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Install or ReplaceAsphalt 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

31 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

"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%
43 neighbors recently requested a quote
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Avatar for Roofing Solutions
Roofing Solutions
4.5(
6
)
Flat, Foam or Single Ply Roofing - Repair- For BusinessAsphalt Shingle Roofing - Install or Replace - 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%
12 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 - 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

"THE ROOF WAS REPLACED QUICKLY AND EFFICIENTLY WITH NO WASTE OF MATERIAL OR TIME. THE CLEAN-UP WAS TOTAL AND THEY LEFT ME NOTHING TO DO BUT ENJOY MY HARBOR BLUE ROOF. I HAVE RECEIVED MANY COMPLIMENTS. ONE SUGGESTION IS: SIGNAGE FOR AML WAS NOT PUT ON THE LAWN. THANK YOU CASEY AND YOUR PLEASANT WORKMEN."
Response time2 days
4 neighbors recently requested a quote
Recommended by70%of homeowners
Request Quote
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

"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%
45 neighbors recently requested a quote
Request 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

"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%
110 neighbors recently requested a quote
Request Quote
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Showing 1-10 of 292
Roofing questions, answered by experts

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.

Proposals, invoices, and estimates are most often used as marketing documents and are not legally binding. Contracts are legally binding documents that detail the service offering, project considerations, and signatures from all parties. If you signed a proposal for discussion purposes while requesting a quote and you decide to hire your roofer, make sure the contracting party follows through with a legally binding contract to protect both parties.

DIY is not recommended due to safety and expertise requirements. Professional installation ensures proper alignment and sealing.

Metal roofs have a reputation for being noisy, but with proper installation and adequate insulation, they are not significantly noisier than shingle roofs. The type of metal used can affect the sound level; for instance, steel roofs are typically noisier than slate or asphalt tiles but quieter than aluminum. While some people find the sound of rain on a metal roof pleasant, you can take steps to reduce the noise. Installing a thicker underlayment, adding insulation between the roof and the house, or using acoustic tiles can effectively muffle the sound. The gauge (thickness) of the metal roofing can also contribute to sound dampening.

A chimney liner is typically easier to install by pushing it down through the chimney with the help of a rope. Depending on your fireplace and the type of liner, installing it by pushing it up through the chimney could work, but operating from the top down is usually the best option.

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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