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  • Average homeowner rating star icon4.5
    Average homeowner rating
  • Verified reviews icon521
    Verified roofing services reviews

Top-Rated Roofers in Bishopville - Updated Nov 2026

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 Bishopville, 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

53 neighbors recently requested a quote
Recommended by95%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 Bishopville, MD and surrounding areas

Approved

In business since 2018

Free estimates

Emergency services offered

"Highly recommend Economy Roofing & Restoration! The entire process was smooth from start to finish. The team was professional, knowledgeable, and easy to work with. Communication was great throughout the project, and they made sure everything was done right. The crew showed up on time, worked efficiently, and did a great job cleaning up afterward. It’s hard to find a company that genuinely cares about its customers and the quality of its work. I wouldn’t hesitate to recommend Economy Roofing to anyone needing roofing, siding, gutters, or restoration work!"
Roof Replacement During Install
Finished Product
Chimney Flashing
Chimney & Step Flashing
Rear Elevation Finished Product

+3

Response time1 day
Response rate90%
88 neighbors recently requested a quote
Avatar for Ocean Waves, LLC
Ocean Waves, LLC
4.7(
30
)
Roof - Clean

Serving Bishopville, MD and surrounding areas

Approved

In business since 1998

Free estimates

Emergency services offered

"Eric and his crew were very professional, courteous, and answered any and all questions that we had. We highly recommend Ocean Waves to everyone who needs a soft wash process for their roof and or siding we also had our gutters cleaned as well. Living here in Ocean Pines our home is surrounded by trees and the amount of debris on our roof was phenomenal it all looks amazing now! Thank you so much! Ron & Robin"
 5 Year Limited Warranty
 Master Business Certification in Roof & Exterior
 Before
 Before & After
 Ocean Waves LLC Safe No-Pressure Roof Cleaning

+13

1 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for Von Marsh LLC DBA Eastern Shore Roofing and Remodeling
Von Marsh LLC DBA Eastern Shore Roofing and Remodeling
5.0(
3
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For Business

Serving Bishopville, MD and surrounding areas

Approved

In business since 2022

Free estimates

Emergency services offered

"Eastern Shore Roofing and remodeling is a company that was professional, punctual and extremely knowledgeable. They responded quickly to my calls, with clear communication. They provided competitive rates and did a great job. I highly recommend Eastern Shore Roofing and Remodeling to anyone looking for reliable, high-quality roofing and remodeling services."
Attention to detail.
Store Front Refresh
Response time1 day
Response rate100%
14 neighbors recently requested a quote
Avatar for Erie Home
Erie Home
4.5(
75
)
Asphalt Shingle Roofing - Install or Replace

Serving Bishopville, MD and surrounding areas

Approved (Corporate)

In business since 1976

Free estimates

Credit card accepted

Erie Home Basement Solutions is a division of Erie Home?a national leader in home improvement since 1976. We have long been known for offering industry-leading solutions to our customers? most pressing needs, and our basement waterproofing, foundation repair, and crawl space services are no exception. When it comes to protecting your home against structural problems, why put the project in anything less than the most capable of hands? At Erie Home Basement Solutions, we provide the effective repair services and personalized service you need to have complete peace of mind.

Drain Tile Install
Drain Tile Install
Drain Tile Install
Drain Tile Install
Drain Tile Install

+20

8 neighbors recently requested a quote
Recommended by89%of homeowners
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Roofing FAQs, answered by experts

Yes, many chimney professionals offer cap installations to prevent debris buildup and animal entry.

Yes, hail damage to your roof can definitely cause water leaks in your roof. This is because hailstones can break, chip, crack, or split shingles of all types, exposing underlayment. This underlayment doesn’t offer as much protection against water, so when it becomes compromised, water can penetrate and leak deeper into your home.

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.

While two-layer torch down roofs are easier to install than three-layer roofing, it is best not to DIY the installation. Torch down roofs require expert knowledge of the application process to get it right the first time and prevent leaks or poor craftsmanship, not to mention that roof work can be dangerous.

Fall is widely considered the best time of year to replace a roof. The moderate temperatures are ideal for roofing crews to work and for new shingles to seal properly. Additionally, autumn weather is often drier, reducing the risk of weather-related delays compared to the rainier spring season.

While spring is also a viable option, the higher chance of rainfall can slow down the project. The main drawback to a fall installation is that it's the peak season for roofers, which can lead to higher prices and scheduling challenges.

To potentially save money, you could consider scheduling your roof replacement during the summer or winter off-seasons. However, both seasons have significant disadvantages. Extreme summer heat can make shingles too soft to handle, while winter's cold, snow, and ice can create dangerous working conditions and prevent shingles from sealing correctly, as they typically require temperatures above 40-45°F.

The Bishopville, MD homeowners’ guide to roofing services

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