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TRUSTED BY HENDERSON, MD HOMEOWNERS

  • Average homeowner rating star icon4.7
    Average homeowner rating
  • Verified reviews icon59
    Verified roofing services reviews

Top-Rated Roofers in Henderson - 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 Henderson, 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
Avatar for Home Genius Exteriors
Home Genius Exteriors
4.9(
388
)
Asphalt Shingle Roofing - Install or Replace

Serving Henderson, MD and surrounding areas

Approved

In business since 2004

Free estimates

Emergency services offered

Elevate your home with Home Genius Exteriors, setting the standard by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It?s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!

Asphalt Roofing
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing

+76

Recommended by96%of homeowners
Callaway Corporations LLC
4.7(
24
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For Business+5 more

Serving Henderson, MD and surrounding areas

Approved

In business since 2009

Free estimates

Credit card accepted

We offer financing and will deal directly with your insurance company if you need assistance. \n \nCallaway Corporations LLC offers a discount to first responders and veterans. With 20+ years of industry experience, we offer top-quality additions, decks, roofing, windows and doors, gutters, and more! Give us a call today! \n

55 neighbors recently requested a quote
Recommended by95%of homeowners
AML Top Quality Construction
4.6(
27
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Install or Replace

Serving Henderson, 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 Economy Restoration, LLC DBA Economy Roofing & Restoration
Economy Restoration, LLC DBA Economy Roofing & Restoration
4.3(
35
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Repair - For Business

Serving Henderson, MD and surrounding areas

Approved

In business since 2018

Free estimates

Emergency services offered

"Jordan Taylor was our rep and did an outstanding of explaining the entire process to us, including how to submit the roof replacement to insurance due to a wind storm. He was super responsive for every question, and he personally got our HOA approval, then walked it through the town govt to get the permit! On the day of installation, his team worked efficiently and quickly, and our roof was completed by late afternoon, including full and thorough cleanup. Jordan came back the next day to walk the property to make sure all garbage was picked up. Economy Restoration will also provide a Quality Control person to go up on the roof for the final inspection, which really gives us a secure feeling. Our roof is amazing, along with the entire process and the pricing is very fair. I highly recommend Jordan and Economy Restoration!"
Roof Replacement During Install
Finished Product
Chimney Flashing
Chimney & Step Flashing
Rear Elevation Finished Product

+3

Response time1 day
Response rate90%
81 neighbors recently requested a quote
Avatar for AAnthony Construction, LLC
AAnthony Construction, LLC
4.9(
11
)
Asphalt Shingle Roofing - Repair

Serving Henderson, MD and surrounding areas

Approved

In business since 2009

Free estimates

Emergency services offered

"Company hired wad quick to do the repair. Employees were friendly and helpful in explaining every aspect of the job as the job was being performed. Inspection at end was walked thru to ensure satisfaction. Would recommend this company to friends and family"
Metal Roofing
Metal Roofing
Metal Roofing
Metal Roofing
Roofing

+23

Response time1 hour
22 neighbors recently requested a quote
Recommended by45%of homeowners
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Roofing FAQs, answered by experts

Homeowners insurance may cover the cost to tarp a roof if the type of damage falls within your coverage. For example, roof damage caused by a natural disaster may fall within your plan, and the cost of a temporary tarp may be incorporated. In general, however, simply tarping your roof for renovations will often not fall under insurance coverage.

Roof repairs average around $1,100 but can easily exceed that for larger repairs. The cost of roof replacement depends on the size of your home and the materials used but averages between $4,000 and $24,000.

Roof work is dangerous and exacting, and a misstep could lead to even more costly repairs, so we do not recommend DIYing. If you are dead set on giving it a go, practice safety measures. Wear a harness, only work during mild weather, and have a partner to help. Potentially DIY-friendly jobs include patching up small leaks, sealing areas around the chimney, and replacing a few shingles.

If you need to replace the roof over your attached garage, a roofing contractor can perform what is called a partial roof replacement that only affects garage roofing. However, it's important to keep in mind that only replacing a portion of your roof creates a situation where your roofing has two different lifespans. You will also miss out on the opportunity for a full roof warranty. In some cases, having two different roofs on your home could increase risks for leaks. When replacing the roof on a detached garage, homeowners have the option to make the project bigger by upgrading their home roof alongside their garage roof. However, this isn't necessary if your home has a newer, properly functioning roof. It is better to try to match the new garage roof to your home's existing roof instead.

For homeowners who plan to stay in their homes for a long time or never want to have to deal with replacing a roof again, rubber roof shingles are likely worth the added investment amount over asphalt shingle varieties. While the initial cost of installing a rubber shingle roof will be significantly higher, their long life spans can be worth it in the long term. Consider the curb appeal of a rubber roof, though, as other roofing materials, like metal, can look better and offer even greater value.

The Henderson, MD homeowners’ guide to roofing services

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