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TRUSTED BY CHESAPEAKE BEACH, MD HOMEOWNERS

  • Average homeowner rating star icon4.4
    Average homeowner rating
  • Verified reviews icon513
    Verified roofing services reviews

Top-Rated Roofers in Chesapeake Beach - Updated Nov 2026

Avatar for Presidential Exteriors LLC
Presidential Exteriors LLC
4.7(
180
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceNatural Slate Roofing - Install or Replace+26 more

Serving Chesapeake Beach, MD and surrounding areas

Approved

Super Service Award Winner

In business since 2015

Free estimates

Warranties offered

"Replacing a roof can be an intimidating project but Presidential Exteriors put us at ease. We were guided through the process and everything went smoothly. The roof looks phenomenal and it's clear the crew put a lot of attention to detail into the job. Very happy and would highly recommend Presidential Exteriors! Specific thanks to David, Nick, Samantha, Shane and the crew!"
Newly installed roof
Windows & Garage Door Replacement
Finished product with brand new siding.
Newly installed roof
Windows & Garage Door Replacement

+44

Response time1 day
Response rate100%
35 neighbors recently requested a quote
Avatar for Roofing Pups, Roofing & Siding
Roofing Pups, Roofing & Siding
4.7(
74
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair+1 more

Serving Chesapeake Beach, MD and surrounding areas

Approved (Corporate)

Super Service Award Winner

In business since 1994

Free estimates

Credit card accepted

"There's nothing worse that dealing with pooring rain and strong winds and then hearing the drip, drip sound of water coming into your home due to a damaged roof. I reached out to roofing repair companies through Angie's list and Roofing Pups responded. Marcus came out the next day and put my fears at ease. The bad news was that I needed a new roof. He showed me my options available, categorized as "good", "better" and "best". Despite my choosing the lowest option, he still threw in some discounts and upgrades at no additional cost. I signed the contract and he arranged for someone to come out at tarp my roof. He even went the extra mile of going to Home Depot and setting up buckets in my attic to catch the water still coming in. The roofing crew came out two days later and gave me a beautiful new roof. They then meticulously cleaned the area. It was great working with Roofing Pups. I couldn't be happier and highly recommend!"
Roof Install
ROOFING PUPS
ROOFING PUPS
ROOFING PUPS
PROJECTS

+4

Response time1 day
Response rate93%
174 neighbors recently requested a quote
Avatar for William Richmond, Inc.
William Richmond, Inc.
5.0(
154
)
Asphalt Shingle Roofing - Install or Replace

Serving Chesapeake Beach, MD and surrounding areas

Approved

In business since 2014

Free estimates

Emergency services offered

"We highly recommend William Richmond Inc services for your projects. Mr. Richmond is professional, straightforward, attentive to customer needs, and regularly check on the work-in-progress at the site personally. The roofing team was on-time, skilled, very efficient, and pleasant despite the long hour and hard work. We are very pleased with our new roof, gutters and shutters."
Complete exterior remodel
Complete exterior remodel
Complete exterior remodel
Complete exterior remodel
Complete exterior remodel

+121

Response time8 hrs
3 neighbors recently requested a quote
Recommended by96%of homeowners
Avatar for AROCON Roofing & Construction
AROCON Roofing & Construction
4.5(
1,458
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair

Serving Chesapeake Beach, MD and surrounding areas

Approved (Corporate)

In business since 2008

Free estimates

Emergency services offered

"Service went great. Available dates were a little backed up but reasonable. The technicians, Mikey and Garret, showed up on time and called with a 20 min ETA. Service was well explained, with pictures, and honest assessment of the roof's condition was given without aggressive upselling. Work was conducted quickly and done well. I used Arocon for my roofing needs at a prior residence and will use their services again."
Standing Seam Roof on Turrent
Standing Seam Roofing job in Mount Airy, MD.
EPDM Rubber Roofing
EPDM Rubber Roofing
Additional Photos

+6

Response time9 hrs
Response rate100%
76 neighbors recently requested a quote
Avatar for The Gutter & Roofing Crew
The Gutter & Roofing Crew
4.8(
72
)
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+3 more

Serving Chesapeake Beach, MD and surrounding areas

Approved

In business since 2018

Free estimates

Emergency services offered

"Miguel was very nice, very knowledgeable about the landscaping questions we asked, and the work was well priced. Edmund cleaned out all the rain gutters and cleaned off the decks afterward, and provided details about our roofs condition that we would have never known. The roof inspection is part of the gutter cleaning package, which was very helpful. We have very steep roofs and he made it look easy, which I know first hand, it is not. We really had a great experience, we will recommend them and hire them again."
Gutters Cleaned Upper Marlboro
Gutters Cleaned
Gutters Cleaned
Huntingtown
Bowie

+2

Response time11 hrs
Recommended by98%of homeowners
Avatar for Charm City Roofing
Charm City Roofing
4.3(
43
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair+26 more

Serving Chesapeake Beach, MD and surrounding areas

Approved

In business since 2008

Free estimates

Emergency services offered

"Charm City Roofing did an excellent job installing my new roof! From start to finish, the team was professional, punctual, and very knowledgeable. They explained the entire process clearly, completed the work efficiently, and left everything clean and neat afterward. The quality of the installation is outstanding, and I feel confident knowing my home is well protected. I highly recommend Charm City Roofing to anyone looking for reliable and top-notch roofing services!"
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+37

Response time8 hrs
Response rate100%
2 neighbors recently requested a quote
Avatar for John Krause Construction
John Krause Construction
4.4(
169
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair+26 more

Serving Chesapeake Beach, MD and surrounding areas

Approved

In business since 1998

Free estimates

Emergency services offered

"Roof & window we're repaired immediately. They showed up the following day after my initial call and provided an accurate estimate. Work commensed right after I signed the contract. The siding took a bit longer due to difficulty matching my 16 yr. old siding (an exact match was no longer being manufactured). I learned this is a common problem. Once an acceptable match was found; the work was completed promptly and correctly. Every effort was made to satisfy me (the customer) and they succeeded. I would hire them again for future needs."
Pool House Exterior with Floor-to-Ceiling Windows & Doors, Two Pergolas, & Cupola with Windows
Modern Farmhouse Kitchen
Luxury Bathroom Renovation with Free-Standing Clawfoot Tub & Chandelier
Pool House - Side Entrance
Modern Farmhouse Kitchen with Farmhouse Sink, Pull-Down Faucet, Stainless Steel Range, Range Hood, Double Wall Oven, and Dishwasher

+113

Response time2 days
Response rate100%
14 neighbors recently requested a quote
...
Showing 1-10 of 419
Roofing FAQs, answered by experts

A roof pitch that’s too shallow won’t shed runoff as quickly, so you have an increased risk of water intrusion through the seams between your roofing materials. In colder climates, snow and ice will accumulate more easily on your roof, which can add enough weight to cause roof collapse and structural damage to your home.

Roofing estimates vary for many reasons, but the most significant ones include differences in the cost of labor based on the contractor’s experience and overhead costs, as well as the quality of the materials your roofer will use for the job. You should get your estimates itemized and make sure your contractors include details about the materials they plan on using. Doing so allows you to compare not only based on the cost but also the value that you’ll get for your money.

You can negotiate roofing payment terms with a contractor, but if you’re working with a reliable, trustworthy roofing contractor, the quote they gave you is probably fair. It’s often not worth haggling over the cost of the job unless you feel it is particularly unfair. If you do, get quotes from other roofing companies to compare prices.

A cool roof is any heat-reflecting roof that rejects solar energy more efficiently than traditional roofing (staying about 50 degrees cooler). Thanks to this ability, a cool roof will make your home cooler on a hot, sunny day. Cool roofs come in a variety of materials, including asphalt, wood, or polymer shingles, clay or concrete tiles, metal, and more.

While the terms are often used interchangeably, wood shakes and wood shingles have notable differences, primarily in their manufacturing and appearance. Wood shingles are machine-cut on both sides, resulting in a smooth, thin, and uniform product. In contrast, wood shakes are typically hand-split or sawed on only one side, giving them a more textured, natural, and rustic appearance. Due to these manufacturing differences, shakes are generally thicker, heavier, and less uniform than shingles. They are also more expensive. Homeowners seeking a more rustic aesthetic often choose shakes, while those preferring a more uniform look may opt for shingles. Both are installed in an overlapping pattern to create a durable, weather-resistant roof.

The Chesapeake Beach, MD homeowners’ guide to roofing services

From average costs to expert advice, get all the answers you need to get your job done.