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TRUSTED BY WOODSBORO, MD HOMEOWNERS

  • Average homeowner rating star icon4.7
    Average homeowner rating
  • Verified reviews icon146
    Verified roofing services reviews

Top-Rated Roofers in Woodsboro - Updated Nov 2026

Avatar for Roofing Pups, Roofing & Siding
Roofing Pups, Roofing & Siding
4.7(
74
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairMetal Roofing - Install or Replace+1 more

Serving Woodsboro, MD and surrounding areas

Approved (Corporate)

Super Service Award Winner

In business since 1994

Free estimates

Credit card accepted

"We had a really good experience with Roofing Pups. Their rep Alex was great to work with, and the roofing crew that came to our house did a good job and cleaned up afterward. We opted to get our gutters replaced as well as our roof, which required a second day of work. The Roofing Pups employee in charge of this job (also named Alex) noticed that the color of the new gutters didnt match our house, and made a point of checking it with us before getting started. We really appreciated this as the new gutters would have clashed with the color of our siding! Everyone with the company was great about making the change, ordering new parts and rescheduling the job. We were very impressed with their service and professionalism. We would definitely use Roofing Pups again!"
Roof Install
ROOFING PUPS
ROOFING PUPS
ROOFING PUPS
PROJECTS

+4

Response time1 day
Response rate93%
172 neighbors recently requested a quote
Roofing With Integrity LLC
4.3(
32
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or Replace

Serving Woodsboro, MD and surrounding areas

Approved

In business since 2025

Free estimates

Credit card accepted

"Roofing with Integrity installed a new roof on my house, build new cement paver steps and install a new side door. In all instances, they did excellent work. Their pricing was fair and TJ, the owner was very responsive. Two of our neightbors expressed in new roof after seeing their work. I would recommend them to anyone."
5 neighbors recently requested a quote
Recommended by88%of homeowners
On Top Home Improvements, Inc.
4.5(
63
)
Asphalt Shingle Roofing - Repair

Serving Woodsboro, MD and surrounding areas

Approved

In business since 1986

Free estimates

Credit card accepted

"Dan Cox, owner of On Top Home Improvement is a true professional, providing quality service and does business the right way, honestly. On Top Home Improvement just completed my home roof replacement in MD and their expertise was nothing short of stellar. I had storm damage and worked through the insurance claim process, which took months. Initially, I hastily contracted another roofing company, a decision that resulted in disappointing service, empty promises, and inflated costs. I fired the first roofing company and paid to get out of their contract. After meeting Dan Cox in person at the property he laid out all options with several pricing options that were reasonable and transparent. His pricing covered all aspects for full roof replacement, with no hidden costs or surprises. After contracting with On Top Home Improvement he assisted with my insurance claim and provided documentation to secure payments for all items covered under my insurance policy. I hold On Top Home Improvement in high regard and recommend their top-notch services. On future project Dan Cox will be my first call."
Response time1 day
Response rate100%
Recommended by98%of homeowners
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Roofing FAQs, answered by experts

Your homeowners insurance premium may increase if you file a roof claim. Whether your rate goes up, and by how much, depends on several factors. These include your insurance company's policies, your personal claim history, the size of the current claim, and the type of damage. While a single claim after a long period without any may not trigger an increase, frequent claims are more likely to raise your premium. Additionally, insurers might increase rates at renewal due to external factors like changing weather patterns, which are beyond your control.

Using a staple gun to hang Christmas lights on your roof or shingles is not recommended. Puncturing your roof with staples can cause damage, leading to cracks, leaks, and exposure to the elements. Staples are also less reliable than other methods like roof clips. For a safer alternative that won't damage your roof, use shingle tabs.

Depending on the condition of your roof, you may be able to add flashing to it. If you’re looking for a way to maintain its integrity while saving some money, you should ask a roofing pro if this is an option. Keep in mind that if your roof is in poor shape, a full replacement may be necessary before flashing is installed.

The level of underlayment’s water resistance will depend on the type of underlayment. The most popular underlayment, felt, is water-resistant, but it can’t withstand long direct exposure to rain or the elements. 

Synthetic underlayment is more waterproof, but asphalt is the only fully waterproof type of underlayment.

The amount of hail damage that warrants a roof replacement depends on the size of the hail. In many cases, a roof replacement is needed if your roof gets hail that is 1 inch or larger in diameter. You may also need to replace a roof due to hail damage if you notice several dents in the shingles or there are seven to 10 hail impact marks within a 10x10 foot area on your roof.

The Woodsboro, MD homeowners’ guide to roofing services

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