Here are the top 5 best roofing contractors in Prince Frederick, Maryland, that homeowners trust—not just for one job, but again and again.
1. Priddy Roofing and Exteriors
What Makes Them The Best Roofing Contractor in Prince Frederick, Maryland:
They’re also one of the few contractors to hold GAF Master Elite® Certification, which means they offer better warranties, install to higher standards, and maintain a near-flawless customer satisfaction rating. Only 2% of roofers nationwide hold this certification.
Beyond roofs, they also install siding, gutters, and offer full exterior remodeling—so your home’s protection and curb appeal are handled by one trusted team.
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What They Offer:
Free inspections with no pressure
Insurance claim assistance from start to finish
Full roof replacement and repair services
Siding, gutters, trim, and more
Serving MD, VA, WV, and PA
Positive Feedback
Room for Improvement:
Why They’re a Great Fit:
2. Simple Solutions Contracting
What Makes Them One of The Best Roofing Contractor in Prince Frederick, Maryland:
They work heavily with single-family homes and are especially good for smaller jobs, repairs, and straightforward replacements. Their tight-knit team means you’re often working directly with the owner, and that hands-on approach shows in their customer satisfaction.
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What They Offer:
Residential roof repairs and replacements
Gutter installation and siding repairs
Emergency tarping and storm response
Serving Prince Frederick and surrounding areas
Positive Reviews
Room For Improvement
Why They’re a Great Fit:
3. G.H. Clark Contractors
What sets them apart:
They have a showroom right in Prince Frederick where homeowners can view materials, ask questions, and make decisions in person. Their team includes trained project managers, experienced crews, and in-house customer service reps to help walk you through the process.
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What They Offer:
Asphalt shingle and flat roofing systems
Siding, window, door, and gutter replacements
Deck builds and trim work
In-town showroom for product selection
Positive Reviews
Room For Improvement
There is and never was an internal pipe leak. I knew where it was leaking before they ever came over. It was leaking around the pipe vent flashing and the water ran down the pipe. The man who came around went up on the roof and caulked around the rubber on the flashing. They never did any work on my pipe joints.” – Rich Cullen
Why They’re a Great Fit:
4. Southernwood Roofing & Siding
What Sets Them Apart:
They’re an Owens Corning Preferred Contractor, which allows them to offer extended warranties on materials and labor. With a reputation for cleanliness, fast turnarounds, and well-coordinated crews, they’re a go-to for full replacements across Southern Maryland.
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What They Offer:
Asphalt, metal, and specialty roofing systems
Siding in vinyl, fiber cement, and engineered wood
Gutter installation and water management upgrades
Extended warranties through major manufacturers
Positive Reviews
Room For Improvement
Why They’re a Great Fit:
5. Paramount Property Solutions, LLC
What Sets Them Apart:
They operate with a restoration mindset—meaning they’re not just patching a roof, they’re bringing your home back to its pre-loss condition (or better). They also handle siding, windows, and other exterior elements, making them a solid pick for comprehensive recovery projects.
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What They Offer:
Insurance-focused roofing repairs and replacements
Siding, window, and full exterior restoration
Assistance with claims, estimates, and adjuster coordination
Positive Reviews
Room For Improvement
Why They’re a Great Fit:
What to Look for in a Roofing Contractor
✅ Show up on time
✅ Do what they say they’ll do
✅ Stand by their work
✅ Know your local weather and codes
Who’s the Right Fit for You?
But if you’re looking for a contractor who:
- Knows how to navigate insurance claims
- Offers premium warranties backed by national brands
- Provides full exterior remodeling
And delivers a clear, simple process that respects your time and budget.
Start with a free inspection from the top-rated local expert.