Best Roofing Companies Near You in Cheswolde, MD (2026)
Top Roofers in Cheswolde, MD
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Freedom Exterior LLC is a family-owned business that customers consistently praise for meticulous attention to detail and exceptional professionalism across power washing, house washing, and exterior cleaning services. Jeff and his team prioritize customer satisfaction through clear communication, timely reminders, and a respectful approach to every project, whether preparing homes for sale or routine maintenance. With quick scheduling, reasonable pricing, and a proven track record of delivering outstanding results on siding, gutters, patios, and walkways, Freedom Exterior LLC has earned strong customer loyalty and recommendations.
"Jeff with Freedom Exterior LLC was fantastic! He treated my house as if it were his own and did an amazing job power washing the exterior in preparation for listing it on the market. It’s refreshing to work with a family-owned business that truly cares — our homes are their homes, too. Jeff and his team made sure I was completely satisfied with the results, and let me tell you, the house looks incredible. I highly recommend Freedom Exterior LLC…" — Alan O.
+1 410-726-6212
This roofing company consistently delivers exceptional work that exceeds customer expectations, with dedicated crews known for their professionalism, respectful demeanor, and commitment to meeting or beating stated timelines. Customers praise their outstanding customer service and friendly approach, with many expressing strong confidence in recommending them and plans to work with them again. Their combination of quality craftsmanship, focused execution, and reliable communication has earned them a reputation as a trusted choice for roofing projects.
"They provide the best work have very respectful workers and they’re dedicated they stay focused and always try to finish a day before the deadline they stated initially" — Edmond H.
+1 443-267-9966
MTO Roofing earns consistent praise from customers for their exceptional professionalism, transparent communication, and high-quality craftsmanship. Clients particularly value the team's proactive insurance claim management, detailed photo updates during projects, and step-by-step explanations of materials and processes that eliminate stress from the renovation experience. The company's commitment to safety, punctuality, cleanliness, and top-tier workmanship—combined with personalized attention from team members like Carlos Montenegro and Jeff Youngman—has made them a trusted choice for roof and siding replacements.
"We had a very positive experience with MTO!!! Jeff, Carlos and their installation crew were professional in every way! They were dependable, punctual, and consistently in communication with us, before, during, and after our roof replacement, and they did a beautiful job!!! Our roof is quite high, large, and has steep contours, so the job was exceptionally challenging and dangerous. Thankfully, the installers were well secured, and implemented…" — Anne W.
+1 301-676-8338
Alliance Construction LLC
Alliance Construction LLC earns consistent praise for expert craftsmanship and exceptional customer service. Customers particularly appreciate owner Marco's deep knowledge of roofing and insurance claims—he proactively identifies missing coverage items and guides clients through the process to maximize their benefits. The team is recognized for thorough communication, detailed inspections with photographic documentation, reliable project completion, and handling complex installations like solar panel removal and steep roof work with professionalism and efficiency.
"So far, I’m very happy with the work completed by this contractor. I’m glad I chose them for the job. Marco is extremely knowledgeable about roof maintenance as well as the insurance process. When we reviewed the estimate approved by the insurance company, he noticed that some items were missing and personally coordinated with the insurance company to have those additional items included. There are no concerns about the workmanship. Everyone on…" — harshad p.
+1 301-466-0143
Anne Arundel Exteriors earns consistent praise for efficient, high-quality roofing work completed in remarkably fast timelines—often one to three hours—combined with fair pricing and honest estimates. Customers consistently highlight owner Jody's exceptional responsiveness, clear communication throughout projects, and the professionalism of his entire team, who maintain meticulous cleanup and attention to detail. The company's reliability, reliability and genuine care for customer satisfaction have made them a trusted recommendation among homeowners for both roof replacements and repairs.
"The entire experience with Jody at Anne Arundel Exteriors was fantastic! This was a first time construction project for us. Jody was knowledgeable and extremely helpful during the planning process. He consistently communicated all updates and construction details, which was insanely helpful during this whole process. Once the project started, it was completed efficiently and meticulously. The team completing the work were wonderful and kept the…" — Allyson B.
+1 410-215-0443
Dunsmore Exteriors consistently earns praise for exceptional craftsmanship, reliability, and responsive communication throughout every project phase. Customers appreciate their efficient execution—completing large jobs ahead of schedule and under budget—combined with knowledgeable, courteous crews who protect work environments and clean thoroughly. Scott and his team stand out for their transparency, competitive pricing, and willingness to answer follow-up questions promptly, making them a trusted choice for roofing, windows, doors, and exterior repairs.
"I met with several window replacement companies before finding Dunsmore Exteriors on a local neighborhood chat. Best decision ever! I hired Dunsmore Exteriors to replace a casement bathroom window that was leaking and it turned out great. Install went smoothly and Scott told me step-by-step what to expect. Pricing was competitive and ordering/install was faster than other larger companies. I liked their service and product so much that I had them…" — dawn C.
+1 410-575-3773
Dogwood Exteriors earns consistent praise for exceptional workmanship, responsive communication, and genuine professionalism throughout every project. Customers particularly appreciate how the team handles insurance claims by serving as advocates—managing adjuster communication, ensuring full coverage, and explaining complex processes in detail—while delivering quality results efficiently and with thorough cleanup. From roof replacements to gutter work, the company's skilled crew (including Sean, Brandon, and Adam) combines technical expertise with a customer-first approach, leaving homeowners confident in their investment and eager to hire them for future projects.
"I was in the market for a new roof because of damage from the past couple of storms. I had spoken to a few contractors before I spoke with Sean at Dogwood Exteriors. I was comfortable from the get go. He listened and answered my many questions. Since it was going to be an insurance claim, I was dreading dealing with the insurance company. Not a problem, Sean worked with the Claims adjuster and met them at my house. I had one conversation with the…" — dawn d.
+1 410-665-6531
Maurice and his team at A-1 Roofings Kangaroof are praised by customers for their professionalism, attention to detail, and reliable communication throughout projects. Clients consistently highlight the quality of their work—from thorough inspections and fast, clean installations to effective leak repairs completed on time—along with fair pricing and warranty coverage that gives homeowners peace of mind. The company's responsiveness to customer questions and commitment to doing exactly what they promise have earned strong recommendations for both residential and commercial roofing needs.
"(Commercial Roof Leak Sealing) Maurice and his team did a great job sealing our roof seams with Endur coating. Maurice was very attentive and responded quickly to calls when questions arose. He came out and gave a fair estimate and did everything he said he would do and on time. I highly recommend Maurice and the A-1 Roofings Kangaroof Team in Columbia Maryland. By Lamont" — Charlee R.
+1 410-799-1600
Solt's Construction & Repair LLC
Solt's Construction earns consistent praise from customers for exceptional attention to detail, thorough workmanship, and responsive problem-solving across projects ranging from kitchen remodels to structural repairs. Owner Caleb and his team—including Kevin and Jack—are recognized for their professionalism, clear communication, and willingness to involve clients in decision-making while keeping projects on timeline. Customers particularly value the company's reasonable pricing, hands-on project management, and commitment to getting every detail right the first time.
"After interviewing multiple home remodelers, I chose Solt’s Construction and I’m very happy that I did. I had a kitchen remodeled with a wall and window removed, electrical rework, and all new cabinets and sink. Solt’s construction added a powder room, front porch and redesigned the outside of a bay window by adding molding and metal roof. I also had front and back doors replaced as well as the siding in the front of the house. Not only did…" — Sylvia B.
+1 410-807-3489
Neighborhood Restoration earns consistent praise for their exceptional customer service, transparent communication, and owner-led attention to detail—with customers highlighting how the team keeps them informed throughout every step of the process and goes above and beyond, such as proactively tarping roofs before repairs and coordinating additional services. Customers particularly appreciate the professionalism and patience of both the office staff and field teams, who explain work in clear, accessible language and deliver quality results that meet or exceed expectations while maintaining competitive pricing. The company's reliability and genuine care for customers have earned strong recommendations, with clients noting the owner's personal involvement in addressing their specific needs and concerns.
"When God Sends Help, Don’t Ignore His Sign! When God sends someone your way to handle problems that you yourself could not find a solution for, you are truly blessed! A terrible storm came through DC and caused my roof to leak. Unfortunately, my insurance company — the same one I’ve paid over $75,000 to over the years — denied my claim. I’ve never received payment for any claim, except for a measly $400 toward my interior damage that actually…" — Renita H.
+1 240-502-0996
Why Hire a Local Roofer in Cheswolde?
Local Climate Knowledge
Cheswolde roofers understand Maryland's specific weather patterns and choose materials built to last in local conditions.
Building Code Compliance
Local contractors know Cheswolde's permit requirements and code standards, ensuring your repair passes inspection.
Faster Response Times
A local company can respond to emergencies quickly and follow up easily if issues arise after the repair.
Typical Roof Repair Costs in Cheswolde
| Repair Type | Typical Cost Range |
|---|---|
| Minor Leak Repair | $150 – $400 |
| Shingle Replacement (small area) | $300 – $900 |
| Flashing Repair | $200 – $600 |
| Gutter Repair / Replacement | $150 – $500 |
| Section Repair (large area) | $1,500 – $5,000 |
| Emergency Repair | $500 – $1,500 |
| Full Roof Replacement | $8,000 – $25,000+ |
* Estimates only. Actual costs vary by scope, materials, and contractor. Get at least 3 quotes.
FAQ: Roof Repair in Cheswolde, MD
Roof repair costs in Cheswolde typically range from $150–$400 for minor leak repairs to $1,500–$5,000 for extensive section repairs. Emergency repairs can cost more. The exact price depends on the extent of damage, roofing material, roof pitch, and the contractor you choose. Always get 3 quotes before committing.
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