Best Roofing Companies Near You in Chestertown, MD (2026)
Top Roofers in Chestertown, MD
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Apex Roofing and Exteriors earns consistent praise for exceptional professionalism, competitive pricing, and superior craftsmanship across roofing, siding, windows, and exterior projects. Customers highlight owner Andy's knowledgeable guidance, clear communication throughout projects, and his team's impressive efficiency—completing complex jobs like 13-window installations in a single day while maintaining meticulous attention to detail. The company consistently goes above and beyond, from including complimentary upgrades to proactively addressing unexpected issues and even completing bonus repairs at no extra charge.
"I had several contractors come out and give estimates for windows, siding, doors, and gutters. Apex gave us a good price and several smaller items that were not included with other companies were included with Apex. I had a good feeling with Andy: he was very professional and knowledgeable from the start and throughout the process. He and his crew had several design suggestions. We were very impressed with the quality of the work and the…" — Robert H.
+1 410-650-2739
Benchmark Roofers earns consistent praise for exceptional craftsmanship, competitive pricing, and outstanding customer service. Customers particularly appreciate the team's professionalism, responsiveness, and attention to detail—from expertly navigating insurance claims to accommodating design adjustments and completing work efficiently. The company's owner and project manager are noted for their involvement and care, ensuring customers feel respected and receive more than they expected.
"I highly recommend Benchmark Roofers. I had four companies come out to perform estimates to replace two roofs, 24 windows, and install new Hardie siding. Of the four, one company insisted over and over that my husband needed to be present. I told them I would not need a price from them. The remaining three companies were all lovely to have out and I asked for competitive proposals. Two of the three indicated that the windows would need to be all…" — Jeanne K.
+1 443-454-1293
First State Roofing & Exteriors earns consistent praise for delivering exceptional value, reliable craftsmanship, and professional service from start to finish. Customers highlight the company's competitive pricing, precise project timelines, meticulous attention to detail, and the owner's hands-on involvement in supervising quality work. The team is commended for clear communication, respectful crew behavior, thorough cleanup, and standing behind their work with guarantees that give homeowners confidence in their investment.
"We had some home projects done and had First State Roofing and Exteriors did the work. Their prices are reasonable and we are extremely pleased with the work they did. All the guys who came to do the work were professional and polite. they cleaned up after themselves and worked hard. We had a leaky window that needed to be fixed, Facia on the roof line to be replaced and new vinyl plank flooring to put down in a room, foyer and 1/2 bath. They…" — Meghan T.
+1 302-222-4065
Elite Exteriors, led by owner James Dove, consistently earns praise from customers for exceptional craftsmanship, professionalism, and reliability across roofing, siding, and exterior renovation projects. Clients particularly appreciate the team's attention to detail, proactive communication throughout projects, and ability to complete work on schedule and within budget. The company's commitment to quality and trustworthiness has made them a preferred recommendation among customers, including other construction professionals and home service business owners.
"I built a new custom designed house and Elite Exteriors installed the metal and shingle roofing, cement siding, all exterior trim, custom rails and column covers, decorative timber beams and a variety of custom carpentry items. As someone who has owned, founded and operated national and regional commercial construction companies for four decades, I admittedly have high standards and expectations for finish and professionalism. James Dove and…" — Robert G.
+1 410-304-2048
Custom Home Renovations, led by owner Jon Purcell, consistently delivers exceptional roofing work with a strong focus on customer service and communication. Customers particularly appreciate the team's professionalism, attention to detail, and willingness to handle insurance coordination—often resulting in full coverage for storm damage repairs. The crew is praised for their respectful approach, meticulous cleanup, availability to answer questions, and fair pricing, with many customers returning for additional projects or referring friends and family.
"Jon and his team are amazing . Jon worked with my insurance to get everything covered. The quality of work was excellent. Him and his team was very respectful to not only me but the stuff in my home. When the inside work had to be done from the water damage they covered everything in plastic and cleaned up everything after the work was done. Jon was great at communicating with me every step of the way and was always available if I needed…" — none n.
+1 443-333-1589
DB Home Remodeling Solutions - Townsend, DE.
DB Home Remodeling Solutions consistently delivers exceptional roofing work backed by thorough communication and meticulous attention to detail. Customers praise owner David Barrientos for his professionalism, transparent pricing that often beats competitor estimates, direct supervision of projects, and clear explanations of materials and work throughout the process. The team is known for completing complex jobs efficiently in a single day, passing inspections without issues, protecting landscaping with tarps, performing magnetic nail cleanup, and handling insurance coordination—all while maintaining courteous, on-time service.
"DB did a fantastic job. We met several times on material selection and everything was delivered several days before the job. His crew was staffed well and they did the entire remove and replace for the complex roof in one day. Replaced 4 sheets of plywood, drip edge, vent boots AND three Velux skylights! They protected shrubs with tarps and swept around the entire house for nails. David personally supervised the work. The dumpster was gone the…" — John D.
+1 800-426-9612
Lucas Home Improvements stands out for exceptional craftsmanship, punctuality, and thorough attention to detail, with customers consistently praising their skilled team's professional execution of roof replacements and repairs. The company is known for competitive pricing, responsive communication from their office staff, and meticulous cleanup practices—including using magnets to ensure no debris is left behind. Customers appreciate the reliability and peace of mind that comes from work completed to the highest standard, with one homeowner noting they can now confidently listen to rain knowing their home is properly protected.
"Lucas Home Improvement surpassed our expectations. We just had our house and deck roofs replaced and they did an amazing job. Lucas and his crew arrived when they said they would and worked for 3 full days to get the job done. As much as you hate having to spend a large amount of money on a part of your house that most people won’t see or pay attention to is tough but what was tougher is hearing it rain and wondering the whole time is this the…" — Kelly E.
+1 443-628-9292
R. Short Roofing
R. Short Roofing earns consistent praise for exceptional professionalism, responsive communication, and fair pricing that delivers outstanding value compared to larger competitors. Customers highlight the team's expertise in quickly diagnosing and resolving complex roofing issues, from leak identification to full roof replacements, while maintaining meticulous attention to cleanup and detail. The company's personable approach, combined with quality workmanship and willingness to tailor solutions to customers' budgets and needs, has made them a trusted choice for homeowners seeking reliable roofing and exterior work.
"We were recommended R. Short from a colleague and are so glad! It was an absolute pleasure working with Rich Chiu from R. Short Roofing. We knew our roof would need replacing soon, but with all the storms the time came sooner rather than later. We did our due diligence and received multiple quotes from larger companies, and smaller businesses alike. Some of the larger companies were absolutely outrageous and had us convinced that we needed more…" — Nicole H.
+1 302-592-1952
Better View Restoration consistently delivers exceptional roofing services with a team known for professionalism, responsiveness, and thorough communication throughout every project phase. Customers particularly appreciate their expertise in navigating insurance claims, including advocating for full roof replacements and offering flexible payment options to ease financial burdens. The company's commitment to quality workmanship, timely project completion, and genuine customer care has earned strong recommendations across multiple roof replacement and restoration projects.
"The dedicated team of Sara, Milder, and Selena worked tirelessly alongside my insurance company to obtain a full roof replacement, instead of settling for the repair that the insurer advocated for to reduce claim costs. Although securing insurance approval took some time, their persistence paid off as they employed various strategies to ensure that the entire roof was covered. Furthermore, recognizing our high out-of-pocket deductible, Better…" — Marie R.
+1 443-231-7176
Matter Roofing and Construction consistently earns praise from customers for their exceptional professionalism, clear communication, and remarkable efficiency—completing full roof installations in a single day while maintaining high quality standards. Customers particularly appreciate the team's helpfulness throughout the insurance claim process, thorough explanations of work, and respectful attention to detail, with many noting that the company goes above and beyond compared to competitors. With a strong track record of prompt service, fair pricing, and meticulous cleanup, Matter Roofing has built customer loyalty that extends to future home improvement projects.
"Nick and his crew were absolutely fantastic! From start to finish, Nick went above and beyond. He helped us navigate the insurance process, gave us an excellent value, and had our entire roof installed in a single day—before 1 p.m.! His communication was outstanding and far better than any other company we contacted. We spoke with several contractors, many of whom never even returned our calls. Even though he was over two hours away from our…" — Spencer K.
+1 443-843-0392
Why Hire a Local Roofer in Chestertown?
Local Climate Knowledge
Chestertown roofers understand Maryland's specific weather patterns and choose materials built to last in local conditions.
Building Code Compliance
Local contractors know Chestertown'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 Chestertown
| 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 Chestertown, MD
Roof repair costs in Chestertown 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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