Licensed Roofing Contractor in Southern Maryland - Crossroads Contracting LLC

Crossroads Contracting LLC is a roofing, siding, and gutter company based in North Beach, Maryland. We work on homes throughout Calvert County and the surrounding area places like Chesapeake Beach, Prince Frederick, Dunkirk, and Huntingtown.
We are not a franchise. We are not a national company with a local phone number. Connor started Crossroads in 2010 and still runs the jobs. The crew you meet at the estimate is the crew that does the work.

YEARS EXPERIENCE

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PROJECTS COMPLETED

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Licensed & Insured

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Google-Rated Contractor

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Years of Trust

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Serving Roofing Services in Calvert County & Southern Maryland

Connor grew up watching how quickly a bad contractor decision could turn into an expensive headache. The homeowners who got burned were not careless they just hired the wrong person and had no way to know it until the damage was done. That is the problem Crossroads was built to solve. Not by being the cheapest option in the area. By being the most straightforward one.

We hold MHIC license #162131 that is the Maryland Home Improvement Commission license the state requires before any contractor can legally work on your home. We are also GAF Certified, which means we have met GAF’s standards for training, insurance, and track record. You can verify both of those things before you sign anything.

The work we do most is roofing, siding, and gutters. Those are the exterior systems that protect everything inside your home. We know them well, and we do not spread ourselves thin trying to do everything.

What We Actually Stand For

Straight talk

We tell you what your home needs, not what makes us the most money. If a repair will hold for another five years, we will say so.

Same crew, start to finish

No subcontractors. The people who show up on day one are the people who finish the job.

Clean sites

We pick up every day before we leave. Nails, packaging, old materials gone before we go home.

Real credentials

MHIC #162131 and GAF Certified. Not just words on a website. Local accountability we live here too. If something is not right, we come back and fix it.

Licensed, Certified, and Insured Here Is What That Means

A lot of contractors in Maryland are not licensed. Some do good work. But if something goes wrong and they are not covered, you are the one left with the problem. We are MHIC licensed (#162131) and fully insured liability and workers compensation. That is the baseline. On top of that, we are GAF Certified.

GAF certification matters for one specific reason: it gives you access to factory-backed warranty options that only certified contractors can offer. That means if something fails with the roofing materials or the installation, the protection comes from GAF not just from us saying we will take care of it. We bring documentation to every estimate. License number, insurance certificate, GAF certification. Ask to see them. You should.

The People Who Show Up at Your House

We keep the crew tight on purpose. A smaller, experienced team does better work than a big rotating roster of subcontractors who have never worked together before. Every person on a Crossroads job has been on plenty of Crossroads jobs before. They know how we do things, they know what the standards are, and they take the same care with your property that they would with their own. Connor is usually on-site for the inspection and the start of every job. He stays reachable throughout not just at the beginning when you are deciding whether to hire us.

Connor Kretzing

Founder of Crossroads Contracting LLC

Built from the Ground Up with Real Experience

Connor is the founder of Crossroads Contracting LLC and has had hands-on experience in residential construction since 2010. Starting in the trades at a young age, he worked his way up from laborer to skilled contractor, gaining real-world experience in roofing, siding, gutters, structural repairs, and exterior renovations.

After seeing too many homeowners taken advantage of by poor workmanship and dishonest contractors, Connor founded Crossroads Contracting LLC with a simple mission: bring honesty, quality, and professionalism back to the construction industry. Having personally performed the work he now oversees, he understands what quality installation should look like and holds every project to those same standards.

Roofing & Restoration Specialist

Connor specializes in roofing systems, storm damage restoration, and insurance claim projects, helping homeowners navigate the repair process from emergency tarping and board-ups to full exterior restoration. His field experience allows him to accurately diagnose problems, communicate clearly with adjusters, and ensure projects are completed correctly the first time.

Today, Connor continues to focus on building a reputation based on trust, craftsmanship, and customer service while growing Crossroads Contracting LLC into a respected exterior contracting company serving Maryland homeowners.

Kyle Murphy Vice President Sales

As Vice President, I bring over 13 years of experience in customer relations, with a strong focus on building trust, delivering exceptional service, and creating long-lasting client relationships. Throughout my career, I’ve developed a deep understanding of what homeowners and businesses need when it comes to reliable, high-quality roofing solutions.

I take pride in ensuring every customer feels heard, respected, and confident in their decisions. My approach is simple: clear communication, honest guidance, and a commitment to excellence from the first conversation to project completion.

Family-Focused Leader & Roofing Professional

Outside of work, I’m a dedicated family person who values time spent with loved ones and believes in treating every customer like part of the family. That mindset carries into my leadership style fostering a team culture built on integrity, accountability, and care.

Whether it’s a small repair or a full roof replacement, I’m committed to helping our customers protect what matters most.

Kyle Murphy

Vice President Sales

Where We Work

Roofing Services in North Beach, MD

Reliable roofing, siding, gutter, and storm repair services helping homeowners in North Beach protect and improve their homes year-round.

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Chesapeake Beach, MD Exterior Services

Reliable roofing, siding, and gutter solutions built to protect Chesapeake Beach homes from coastal weather, storms, and long-term wear.

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Prince Frederick, MD Roofing Services

Roofing, siding, and gutter solutions in Prince Frederick, MD designed to protect homes from storms and everyday wear.

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Roofing & Repair Services in Dunkirk, MD

Reliable home protection solutions in Dunkirk, MD focused on storm damage repair, leak prevention, and keeping your roof and exterior systems performing strong through every season.

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Roofing Services in Huntingtown, MD

Dependable roof repair and replacement services in Huntingtown, MD designed to handle storm damage, aging materials, and seasonal weather challenges while keeping your home protected year-round.

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Home Repair & Protection in Calvert County, MD

Reliable solutions for storm damage, exterior wear, and ongoing home maintenance across Calvert County, MD to keep your property safe, strong, and well-maintained year-round.

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Storm Damage & Home Repair in St. Mary’s County, MD

Practical, long-lasting solutions for storm damage, leaks, and general home exterior issues across St. Mary’s County, MD to keep your property protected and well-maintained year-round.

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Exterior Repair & Weather Protection in Charles County, MD

Reliable home solutions across Charles County, MD focused on fixing storm damage, preventing leaks, and strengthening your home against seasonal weather wear for long-term protection.

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Home Exterior Solutions in Anne Arundel County, MD

Trusted repair and maintenance services across Anne Arundel County, MD focused on protecting homes from storm damage, water intrusion, and everyday wear with durable, long-term solutions.

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Home Repair Services in Prince George’s County, MD

Reliable solutions for storm damage, leaks, and exterior wear to keep homes across Prince George’s County protected and in strong condition year-round.

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Home Protection Services in Montgomery County, MD

Dependable repair and maintenance solutions across Montgomery County, MD focused on preventing damage, fixing issues early, and keeping homes strong through every season.

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Siding Repair & Maintenance in Howard County, MD

Reliable solutions across Howard County, MD for storm damage, leaks, and general home upkeep to keep your property protected and in good condition year-round.

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What Maryland Homeowners Are Saying

    
 
 
      Trustindex verifies that the original source of the review is Google. A Big Shout out to Connor!! Needed something done asap due to settlement and he took care of it right away!! Took the worry right off my hands and followed through exactly as he said he would. Not many businesses work this way anymore unfortunately, If you need any help done Contact Crossroads , you will be just as Happy as me, I am sure!!!
  
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   Kristy Conover 
 
 
 
 
     Trustindex verifies that the original source of the review is Google. Connor is amazing! My wife and I recently moved to the Pax River area and needed help with some upgrades on our new home. Connor was punctual, provided assistance exactly where we needed and even gave helpful advice for future upgrades/maintenance. I'd definitely recommend him to anyone in need of a general contractor.
  
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   Chadd Russell 
 
 
 
 
     Trustindex verifies that the original source of the review is Google. I recently hired Crossroads Contracting to update my basement, and I couldn’t be happier with the results. They painted the walls, repaired drywall, refinished the kitchen cabinets, and even replaced the bathroom vanity. The quality of their work was excellent, and they were extremely friendly and professional throughout the process.

What really stood out was their responsiveness—any time I had a concern, they came back promptly and fixed it quickly without any argument. It’s rare to find a company that combines skill, efficiency, and such a great attitude. I would highly recommend Crossroads Contracting to anyone looking for top-notch home improvement work.
  
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   Tobias Larsen 
 
 
 
 
     Trustindex verifies that the original source of the review is Google. Once again, Connor (Cross Roads Contracting) and his crew swept in, built-out a great looking deck, on time and on budget.  I would highly recommend using Cross Roads in the future!!
  
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   Roger Lord 
 
 
 
 
     Trustindex verifies that the original source of the review is Google. Connor and his crew did a great job!  Expertly navigated the Calvert Country permit process, tore down the old deck, installed the new deck in three days, left the site clear of debris, stayed on schedule and budget!!
  
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   Roger Lord 
 
 
 
 
     Trustindex verifies that the original source of the review is Google. They were able to come by and fix some water damage I had in my bathroom. I practically have a new bathroom it looks like. Timely also.
  
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   Steven Patrick 
 
 
 
 
     Trustindex verifies that the original source of the review is Google. I’ve had so many projects done by them and every single time I give my ideas and what I want and Connor makes it better than I could’ve ever dreamed! Super professional, incredibly talented, and even more driven to exceed homeowner expectations! Any time I need anything done in my home, I call Connor and he fits me in quickly! I wouldn’t go anywhere else! He turned an ugly and unusable space into my favorite place to be. I never leave reviews, but trust me when I tell you- call them! You won’t be disappointed!
  
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   Lisa Elborne 
 
 
 
 
     Trustindex verifies that the original source of the review is Google. Connor has been doing a lot of work for my sellers and I have received nothing but great reviews. If you have a project in mind, he would be the first one I call.
  
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   Jeffrey Lewis 
 
 
 
 
     Trustindex verifies that the original source of the review is Google. Connor and his crew do exceptional work and are very fair on price
  
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   brandon_lml472

If you want to know more about who we are

Before you commit to anything, that is completely reasonable. Call us at +1 443-219-7323 or use the contact form. The inspection is free and there is no obligation to move forward after.