Trusted Roofing Contractor in Southern Maryland

Q: Do you offer siding and gutters along with roofing?

Yes. Crossroads Contracting specializes in roofing, siding, and gutter services. Homeowners may combine these services into one exterior improvement project, and free estimates are available.

Q: How do I get started?

Call +1 443-219-7323 or use the website contact form to schedule a free inspection and estimate. The team will assess the home's exterior and provide a transparent, no-pressure estimate.

Q: Does my homeowner's insurance cover roof replacement in Maryland?

Coverage depends on the cause of the roof damage. Many homeowner insurance policies cover storm, wind, hail, or falling-debris damage, but normally do not cover damage caused by aging or ordinary wear. Crossroads Contracting can inspect and document storm damage and assist with the insurance claim process.

Your home is one of your most important investments. When it comes to your roof, siding, or gutters, you need a contractor who takes that responsibility seriously. Crossroads Contracting LLC is GAF Certified and holds MHIC License #162131, meaning we meet in Southern Maryland’s strict standards for roofing contractors. We show up on time, communicate clearly, and do the work right the first time.

YEARS EXPERIENCE

1 +

PROJECTS COMPLETED

1 +

Licensed & Insured

1 %

Google-Rated Contractor

1 +

Southern Maryland's Trusted Roofing, Siding & Gutter Contractor

Hiring a contractor shouldn’t feel like a gamble. At Crossroads Contracting LLC — based in North Beach, MD and serving all of Southern Maryland — we built our business the old-fashioned way: by doing the work right and letting our results speak for themselves. From Calvert County to Charles County to St. Mary’s County, homeowners trust us to protect their most valuable investment.

Connor and the Crossroads team have been protecting Southern Maryland homes since 2010. We specialize in roofing, siding, and gutter systems the exterior elements that stand between your family and the weather. We don’t upsell. We don’t cut corners. And we don’t disappear after the job is done.

Professional Roofing Services Built for Southern Maryland

Roofing Installation & Replacement

Protect your home with a new roof built to handle Maryland storms, humidity, and harsh winters. We install asphalt shingle, architectural, and specialty roofing systems with a warranty you can count on.

Siding Installation & Replacement

New siding protects your home from moisture and weather damage while dramatically improving curb appeal. We install vinyl, fiber cement, and engineered wood siding for Maryland homeowners.

Gutter Installation & Repair

Properly functioning gutters protect your foundation, siding, and landscaping from water damage. We install seamless aluminum gutters and gutter guards built for Maryland's heavy rain seasons.

Storm Damage to Your Roof or Siding? We Can Help.

Southern Maryland homeowners deal with heavy thunderstorms, high winds, and hail every year. If your roof, siding, or gutters have been damaged, Crossroads Contracting LLC is here to help fast.

We offer free storm damage inspections and can work directly with your insurance company to help document the damage and ensure your claim covers the full scope of repairs. You shouldn’t have to fight your insurance company alone.

Flexible Financing Available Protect Your Home Today

A new roof or siding replacement is a significant investment but it shouldn’t be out of reach. We offer flexible financing options to help Southern Maryland homeowners get the protection their home needs without waiting.

Recent Roofing Projects In Southern Maryland & Surrounding areas

Explore our portfolio of completed projects showcasing our commitment to quality craftsmanship.

Before After

Aerial drone view of shingle bundles staged on Southern Maryland roof during replacement — Crossroads Contracting LLC

Drone aerial view of completed roof repair on Maryland home — Crossroads Contracting LLC

Before After

Before photo of deteriorated roof in Saint Leonard MD prior to replacement — Crossroads Contracting LLC

After photo of roof replacement project Saint Leonard Maryland — Crossroads Contracting LLC

Before After

Drone aerial shot of vinyl siding replacement underway on Southern Maryland home — Crossroads Contracting LLC

Drone view of roof repair and shingle installation Southern Maryland — Crossroads Contracting LLC

Our Residential & Commercial Roofing Services

ROOF REPLACEMENT

Upgrade your home with roof replacement using durable materials, workmanship, and lasting protection.

View Roof Replacement Details

ROOF REPAIR

Protect your home with professional roof repairs done with precision, quality materials, and lasting results.

Roof Repair Projects

STORM REPAIR

Quick and dependable storm damage repair to restore your home and protect it from further issues.

Storm Damage Solutions

ROOF INSPECTIONS

Detailed inspections designed to catch damage, leaks, and wear before they become major problems.

Roof Inspection Details

SIDING

Upgrade your home’s exterior with durable, weather-resistant siding that enhances protection and curb appeal.

Siding Installation Options

WINDOWS

Enhance your home with energy-efficient windows that improve comfort, lighting, and overall performance.

Window Replacement Details

DOORS

Upgrade your entryways with professionally installed doors built for strength and long-lasting performance.

Door Installation Solutions

GUTTERS

We provide high-quality gutter solutions that direct water away from your home and foundation.

Gutter System Solutions

What Southern 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!!!
  
  Posted on Google  
 
    
   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.
  
  Posted on Google  
 
    
   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.
  
  Posted on Google  
 
    
   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!!
  
  Posted on Google  
 
    
   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!!
  
  Posted on Google  
 
    
   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.
  
  Posted on Google  
 
    
   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!
  
  Posted on Google  
 
    
   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.
  
  Posted on Google  
 
    
   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
  
  Posted on Google  
 
    
   brandon_lml472

Frequently Asked Questions About Roofing in Southern Maryland

How do I know if I need a new roof or just a repair?

The age of your roof is the biggest factor. Most asphalt shingle roofs last 20–25 years. Signs you may need a replacement include: missing or curling shingles, granules in gutters, daylight visible from the attic, or multiple leaks in different areas. If your roof is under 15 years old and the damage is localized, a repair may be sufficient. We offer free inspections to give you an honest assessment — no obligation.

How long does a roof replacement take?

Most residential roof replacements in Southern Maryland are completed in one to two days depending on the size of the roof and weather conditions. We’ll give you a specific timeline before work begins. We also clean up all debris and nails before leaving — so your property looks better than when we arrived.

What roofing materials do you install?

We install architectural asphalt shingles, 3-tab shingles, and specialty roofing products from leading manufacturers. We’ll recommend the best system for your home’s structure, your budget, and the specific weather conditions in your area of Southern Maryland. We only use materials we’d put on our own homes.

Do you offer siding and gutters along with roofing?

Yes — we specialize in all three exterior services. Many homeowners combine roofing, siding, and gutter replacement into a single project to save on mobilization costs and avoid having multiple contractors on site. We offer free estimates for any combination of exterior work.

How do I get started?

Call us at +1 443-219-7323 or use the contact form on this page to schedule a free inspection and estimate. We’ll schedule a walk-through at a time that’s convenient for you, assess your home’s exterior, and provide a transparent, no-pressure estimate.

Does my homeowner's insurance cover roof replacement in Maryland?

It depends on the cause of damage. Most homeowner’s insurance policies cover roof damage caused by storms, wind, hail, or falling debris. They typically do not cover damage from normal wear and aging. If your roof was damaged in a storm, we can help you inspect the damage, document it properly, and work with your insurance adjuster to file a claim — at no cost to you.

Results You Can Trust.

Your message was sent!

Thank you! We'll be in touch soon.

Serving Southern Maryland & Surrounding Communities

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.

Read More North Beach Roofing Service

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.

Read More Chesapeake Exterior Service

Prince Frederick, MD Roofing Services

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

Read More Prince Frederick Roofing Service

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.

Read More Dunkirk Roofing Service

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.

Read More Huntingtown Roofing Service

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.

Read More Calvert County Home Repair

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.

Read More St. Mary’s Storm Damage

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.

Read More Charles Exterior Repair

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.

Read More Anne Arundel Home Exterior

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.

Read More Prince George’s Home Repair

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.

Read More Montgomery Home Protection

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.

Read More Howard Siding Repair

Not Sure If You Need a New Roof? Get a Free Inspection.

Crossroads Contracting LLC offers free, no-obligation roof inspections for Southern Maryland homeowners. We’ll assess your roof’s condition, check for damage or wear, and give you an honest recommendation whether that’s a repair, replacement, or nothing at all.