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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 CHESAPEAKE ROOFING WINDOWS & SIDING
CHESAPEAKE ROOFING WINDOWS & SIDING
4.9(
106
)

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
Avatar for Roofing Pups, Roofing & Siding
Roofing Pups, Roofing & Siding
4.7(
66
)

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%
265 neighbors recently requested a quote
Avatar for Spicer Bros. Construction Inc.
Spicer Bros. Construction Inc.
4.6(
78
)

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%
41 neighbors recently requested a quote
Avatar for Roofing Solutions
Roofing Solutions
4.5(
6
)

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%
13 neighbors recently requested a quote
Avatar for New Castle Constructs, LLC
New Castle Constructs, LLC
4.9(
31
)

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
)

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
)

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%
112 neighbors recently requested a quote
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Roofing questions, answered by experts

White is the most energy-efficient color for roofs because solar energy reflects off white surfaces the best. Silver is also a good choice.

A gable roof with steep pitches covered in asphalt shingles or wood shakes is the most popular roof for Cape Cod homes. Asphalt shingles started gaining popularity in the early 1900s, so wood shake roofs, which were popular in the 1700s when Cape Cod homes were first built, are the traditional option. You can further modernize your Cape Cod home by raising the roof in the front, back, or both to add living space and change up the traditional single-gable roof with doghouse dormers.

Rubber shingles last for around 30 years, on average, and some can last for and include warranties for up to 50 years. Rubber roof shingles are more expensive than asphalt shingles, but they can last up to twice as long, meaning they provide more value in the long run. Just keep in mind that rubber roofs often require more maintenance than asphalt shingle roofs, including routine cleaning to avoid mold growth. Ask the roofer who installed your roof for an estimate for routine cleaning, if necessary.

Roof vents are an essential part of a roof, as they promote energy efficiency by keeping warm, humid air at bay. The roofing material, especially asphalt shingles, will not last as long as it should (about half of its manufacture life) if the attic is not ventilated. Also, going without ventilation means having a warm attic that demands more from your air conditioning system (and your wallet, once the bills come). Ridge vents and roof vents also prevent a host of other icky moisture-related problems like rot, mold, and mildew.

Yes, shingle brand can affect bundle sizes, with some brands weighing more than others and having slightly differing numbers of shingles.

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.