We Have Been Taking Care of Southern Maryland Homes Since 2010

Crossroads Contracting 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 EXPIERIENCE

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PROJECTS COMPLETED

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Licensed & Insured

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Google-Rated Contractor

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The Story Behind Crossroads

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 nearly 14 years of hands-on experience in residential construction. 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 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 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

What Maryland Homeowners Are Saying

If you want to know more about who we are

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