When your roof starts showing signs of wear—or worse, takes a hit from a storm—you need more than just someone to swing a hammer. You need a team that will show up, explain things clearly, and deliver solid work that protects your home long after they’ve left the driveway.
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
The Go-To Team for Storm Damage, Insurance Restoration & Total Exterior Remodels
What Makes Them The Best Roofing Contractor in Prince Frederick, Maryland:
This crew leads the way in storm damage restoration and insurance-based roofing work in the Mid-Atlantic. When severe weather hits, they know how to inspect, document, and work directly with insurance adjusters to make sure nothing gets missed. They don’t leave you guessing—they show you exactly what needs to happen and why.
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.
Phone
443-771-7495
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
“Justin Mefford of Priddy Roofing And Exteriors runs a top-notch company. This company under his leadership gets things done, fast, and perfect the first time. You are never going to find a more honest Roofing and Exterior Company that has your best interests in mind. They will get all your projects done perfectly and at amazing prices that their competitors can’t even come close to matching. Give Justin Mefford and Priddy Roofing and Exteriors all your window, roofing, siding, gutters, downspout work and you will be very pleased you did. He and all his people are courteous, respectful, timely, from the moment they propose the job through completion. Not a speck of debris is left after they complete the job. You will look forward to working with them as often as possible. As a retired Army Colonel with 34 years of service, I give Justin and his Priddy Roofing and Exteriors my highest rating!” – George Carter
Room for Improvement:
“Priddy roofing and exteriors were quick and professional when coming out and giving an estimate on the repairs needed. We ran into a couple of speed bumps with things that were lost in translation, but they wasted no time in clearing up any discrepancies. They made sure that the repairs were immaculate before they would accept payment. Very happy with the finished product and would use them again in the future if needed.” – Emanuel Chavira
Why They’re a Great Fit:
If you’ve experienced storm damage or just want a stress-free path to a new roof, this team offers structure, guidance, and unmatched professionalism from the first call. That is why we are putting them on the list of the best roofing contractors in Prince Frederick, Maryland.
2. Simple Solutions Contracting
Straightforward, Reliable Roofing with Local Heart
What Makes Them One of The Best Roofing Contractor in Prince Frederick, Maryland:
Simple Solutions is exactly what the name says—simple, honest, and reliable. This family-run contractor focuses on making roofing easy for the average homeowner. No fluff, no runaround—just accurate inspections, honest pricing, and strong follow-through.
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.
Website
www.wefindsimplesolutions.com
Phone
443-968-8689
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
“I’ve never known a company who goes above and beyond for their customers like this company here! I really appreciate the consistency, the consideration, and the timely manner in which they took care of our needed repair. They have a kind and knowledgeable team ready to help with anything we need, and I’d fully trust and recommend them to everyone. I love Simple Solutions and definitely plan to contact them again in the future!” – Anja Blackerby
Room For Improvement
“Walked out of renovation job after 8 weeks. Had no indication there were issues until the day prior. Seven rooms being worked on and are in different levels of finishing. Approximately 35% of the original contract is unfilled. Payment was primarily for service, the majority of supplies purchased by homeowner (cabinets, tile for multiple rooms, etc). Damaged/destroyed several items in home with no acknowledgement that fault was that of contractor. Destroyed fireplace mantel. Destroyed full size room rug during floor refinishing process. When asked about it, claimed spouse had ok’d. When spouse asked same question, he claimed I had ok’d it. Several times throughout the 8 weeks, he tried to play us off each other when he would do something wrong. We have paid approximately 75% of the original proposal. Contractor left job site with no notice and destroyed material (travertine tile) purchased by homeowner and then 2 days later sent a letter saying we were asking too much of him after the fact. Letter stated we owed an additional $3200 for services that were add-ons, All proposed add-ons were part of the original contract. Letter also stated that we owed sub-contractors money because we had not paid him the full amount. Sub-contractors had not completed jobs either.” – Anonymous
Why They’re a Great Fit:
For homeowners who want clear answers, fast response times, and a team that treats your home like their own, Simple Solutions is an excellent choice—especially for quick repairs and local service.
3. G.H. Clark Contractors
A Longstanding Name in Prince Frederick for Roofing & Full Exterior Remodeling
What sets them apart:
With over 25 years serving Southern Maryland, G.H. Clark Contractors has become a trusted local brand. They’re well-known in Calvert County for offering full-service exterior work under one roof. From windows to decks to roofs, this team does it all.
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.
Website
www.ghclark.com
Phone
410-414-7060
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
“I had my roof replaced a few days ago and I must say I was so impressed with the quality of work that G.H. Clark Contractors put in replacing my roof. Working with them was such a pleasure from start to finish. Gil Clark Sr., who was referred to me by a friend, was very courteous, professional, and timely. I will go to Gil and his company anytime in the future and refer anyone that needs their roof replaced because I am so pleased with the job they did.” – Darshana R.
Room For Improvement
“Had them install a new roof on my house. After several months we ended up with a leak in an upstairs bedroom. They sent someone over who ended up caulking around a pipe on the roof. Asked about the damage to the ceiling and at first they said they would fix it, then they decided it maybe leaking inside the pipe. They said the would check it out and if it’s not the pipe they would repair the damage. It has been many months now and nothing is being done. The roof has never leaked again but the damage to the ceiling is still there.
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:
If you’re looking for more than just a roof—maybe a new deck or upgraded windows as well—G.H. Clark offers the tools and expertise to handle a full exterior overhaul without juggling multiple contractors. That is why we are putting them on the list of the best roofing contractors in Prince Frederick, Maryland.
4. Southernwood Roofing & Siding
Efficiency, Scale & Strong Manufacturer Partnerships
What Sets Them Apart:
Southernwood Roofing & Siding brings a professional, production-focused approach to residential roofing. Their crews are trained for speed and precision, making them a top pick for homeowners who want a roof installed efficiently—with minimal disruption.
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.
Website
www.southernwoodllc.com
Phone
301-934-0043
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
“Southernwood Roofing did an excellent job replacing my 25 year old roof. I was blown away by the kindness and respect of the crew. No swearing, no loud music, just hardworking men. They did a big roof with multiple angles in one day. And THEY CLEANED UP their mess. No nails or trash to be found! I am just super impressed. Excellent work, excellent crew. Andrew the salesman was excellent to work with also. Very easy going, answered all my questions. I HIGHLY RECOMMEND Southernwood Roofing. You won’t go wrong selecting them for your roofing needs. I would use them again in a heartbeat.” – First Last
Room For Improvement
“Do not believe the reviews. As a resident of Southern Maryland and owner of several homes, I can honestly say this is the worst customer service I have ever had for roofing or with any contractor. 5 Trips out to my house and due to constant “emergencies” the work has still not been done.” – Matthew Johnson
Why They’re a Great Fit:
If you’re on a timeline and want a fast, reliable roof replacement with strong warranties, Southernwood brings the muscle and systems to get it done right—without delays. That is why we are putting them on the list of the best roofing contractors in Prince Frederick, Maryland.
5. Paramount Property Solutions, LLC
Focused on Insurance Restoration and Project Coordination
What Sets Them Apart:
When storm damage hits, navigating the insurance process can feel like a full-time job. Paramount Property Solutions helps shoulder that burden, guiding homeowners through the claims process while delivering professional-grade roof replacements.
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.
Website
www.paramountpropsolutions.com
Phone
301-684-0343
What They Offer:
Insurance-focused roofing repairs and replacements
Siding, window, and full exterior restoration
Assistance with claims, estimates, and adjuster coordination
Positive Reviews
“Just had my roof replaced and I’m extremely pleased with how the project went, start to finish. After I explained some of the issues with my existing roof, Will gave me different options I had to fix those issues and supplied me with estimates almost immediately. The work was scheduled quickly and the job was done in a day. The crew were efficient and very clean. I will be using Paramount again soon to have my gutters replaced.” – Teresa Gallion
Room For Improvement
None!
Why They’re a Great Fit:
If you’re feeling overwhelmed after a storm and need a contractor who will handle both the work and the paperwork, Paramount offers experience, organization, and peace of mind. That is why we are putting them on the list of the best roofing contractors in Prince Frederick, Maryland.
What to Look for in a Roofing Contractor
The best roofing contractors aren’t just the ones with the fanciest websites or biggest ads—they’re the ones who:
✅ Communicate clearly
✅ Show up on time
✅ Do what they say they’ll do
✅ Stand by their work
✅ Know your local weather and codes
✅ 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?
The best roofing contractors aren’t just the ones with the fanciest websites or biggest ads—they’re the ones who:
Every home is different—and every roofing project has its own set of challenges. The five contractors listed above all bring something unique to the table.
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.
