Best Roof Repair in Chestertown, MD — Top Roofers (2026)
Top Roofers in Chestertown, MD
Filter by service:
Home Crafters Roofing earns consistent praise for exceptional professionalism, fair pricing, and swift completion of work. Customers particularly appreciate owner George's responsiveness—returning calls the same day, providing quick estimates, and completing projects faster than expected—along with the team's skilled craftsmanship and clear communication throughout the process. The family-owned business is repeatedly recommended for treating customers with care while delivering high-quality results on roof repairs, replacements, and gutter work.
"At the beginning of this process I didn't have a clue what to expect. Looking into getting a new roof for my old house was quite terrifying, she's an old gal (just turned 100) with quite a steep pitched roof. Figured i was probably going to have to strong arm someone into replacing it. Within minutes of searching for roofing companies in the area I was absolutely shocked at the amount of reviews home crafters roofing and contracting had. Honestly…" — Algebra *.
+1 410-882-7663
Tar Heel Construction Group consistently delivers exceptional craftsmanship and attention to detail across roofing, siding, and exterior projects, with customers praising their skilled crews and meticulous clean-up work. The company prioritizes customer satisfaction through responsive project managers and team members who listen to feedback, answer questions thoroughly, and go above and beyond to ensure clients are completely happy with the final result. Customers also appreciate their reasonable pricing, professional demeanor, and ability to handle both standard and complex custom projects with efficiency and care.
"I cannot say enough about this wonderful company!! When my insurance company would not cooperate, Tar Heel was there to ease my stresses. I had a beautiful new roof put on my 20+ year old townhouse in Abingdon today. Everyone was great to work with. Ashley was pleasant with each phone conversation and walked me through everything so that this single woman could understand it. Tristan made sure everything about the roof install went smooth. And…" — Wendy J.
+1 410-671-0735
CRG Roofing consistently delivers top-quality craftsmanship and meticulous attention to detail, with customers praising their expert installation work and thorough cleanup on every project. The team is known for exceptional professionalism and communication throughout the entire process—from initial consultation through project completion—including valuable support with insurance claims and flexible scheduling to meet customer timelines. Customers particularly appreciate the company's care and respect for their properties, fair pricing, and genuine commitment to customer satisfaction, making them a trusted choice for both emergency repairs and major roof replacements.
"We called CRG through a family recommendation. We connected with Daniel Ahn and from the first moment we spoke to him we realized he knew what he was doing. Daniel helped us file our insurance claim and when we were refused for our claim, Daniel walked us through the steps to finally get our claim approved. The day of install we had a great crew! They laid large tarps over all of our bushes so they did not get damaged or dirty. The team worked…" — Lynn C.
+1 410-847-7663
ALP Roofing consistently earns praise for exceptional professionalism, reliability, and honest customer service that goes beyond typical roofing work. Customers highlight the team's punctuality, meticulous attention to detail, and genuine care—including crew members who identify and fix problems at no charge, handle insurance coordination seamlessly, and complete jobs with spotless cleanup. The company's leadership, particularly Cole and Brenden, is noted for their responsiveness, transparency in recommendations, and willingness to address customer needs, earning repeat business and enthusiastic referrals from satisfied homeowners.
"I had such a great experience with this company from start to finish. Everyone I talked to was super friendly and helpful — from the staff who answered the phones to Cole, who came out to look at the roof. I originally just wanted an estimate for a replacement, but instead of trying to sell me something I didn’t need, they were honest and told me the roof is old but doesn’t need to be replaced right away. Cole also pointed out a few small issues…" — Street B.
+1 410-600-7663
Economy Roofing earns consistent praise from customers for their exceptional professionalism, clear communication, and high-quality workmanship across roof replacements, repairs, and restoration projects. Clients highlight the team's efficiency—completing full roof replacements in a single day—competitive pricing, and willingness to work closely with insurance claims to advocate on behalf of homeowners. The company's friendly, accommodating approach and meticulous attention to detail, from demo and installation to final cleanup, have earned strong recommendations from satisfied customers.
"We hired Economy Roofing when we had roof damage from a storm. This company came recommended from a friend. The company came to our residence to check out the damage, provide the necessary paperwork to file a claim with our insurance company. The process was done in a timely manner and with professionalism. Once the insurance company accessed the damages and approved the claim we met the with the project manager Sean Gleason who walked us through…" — Anna F.
+1 410-449-7444
Customers consistently praise Highmark Construction for their exceptional professionalism, clear communication, and meticulous attention to detail throughout every project stage. Team members like Matt, Steve, Chevy, and Peter are recognized for guiding customers through the insurance claims process, answering questions thoroughly, and ensuring projects are completed on schedule with outstanding craftsmanship. The company stands out for its commitment to quality finishing work—including thorough cleanup and follow-up service—demonstrating a genuine dedication to customer satisfaction rather than simply completing jobs and moving on.
"Just want to say a public thank you to the folks at Highmark Construction. Their crew recently replaced the roof of my townhome and subsequently did some repair on my gutters. From the start, Matt was amazing. He answered a million silly questions for me and helped to guide me through the insurance process. Everything went very smoothly and with low stress due to his assistance. The day the roofers came to do the work I was nervous - but they…" — Stephanie S.
+1 410-505-0605
Black Anchor Roofing earns consistent praise for exceptional craftsmanship, attention to detail, and use of quality materials throughout every project. Customers particularly value the team's professionalism and clear communication, with owner Ricky and crew chief Jose consistently recognized for their responsiveness, expertise, and willingness to go above and beyond—from assisting with insurance claims to completing complex jobs in a single day. The company is also noted for fair pricing and reliable service, making them a trusted choice for roofing, gutters, and related work.
"I give Black Anchor Roofing 5 stars without hesitation! For a small roofing company I was impressed with their level of maturity and knowledge of the roofing and gutter industry. I was approved for a new roof under an insurance claim and I chose Black Anchor Roofing to do the job. The day of my insurance claim roof inspection, Ricky, the owner of Black Anchor Roofing met the claims adjuster on site to offer any assistance in identifying the…" — Michael
+1 410-205-9562
Kelbie Home Improvement Inc - Baltimore Flat Roof Services
Kelbie Home Improvement stands out for exceptional responsiveness and owner involvement—Mike Kelbie personally returns calls within minutes and provides same-day or next-day inspections, even for emergency repairs. Customers consistently praise the quality of their work, clear communication, and fair pricing, with detailed written estimates that include all materials, labor, and cleanup, plus generous warranties covering both materials and workmanship. The team demonstrates professionalism and conscientiousness throughout projects, from protecting neighboring properties during work to going beyond initial agreements at no extra charge, making them a trusted choice for flat roof repairs and coating work across Maryland.
"I own a townhouse in the Federal Hill/Riverside neighborhood of Baltimore City. Last week there was a big rain storm and I woke up to the ceiling in my room leaking water. I called Kelbie Home Improvement that afternoon. I spoke with someone who took my details and said I would get a call back to discuss the issue and next steps. Not 5 minutes after I hung up, Mike Kelbie, the owner of the company, called back personally. He was very nice and…" — Kelsey B.
+1 410-766-3377
Monarch Roofing earns consistent praise for exceptional professionalism, responsive communication, and meticulous attention to detail throughout every project phase. Customers consistently highlight competitive pricing, efficient project completion, thorough cleanup, and comprehensive documentation with photos—with owner David frequently present on-site to oversee quality. The team's reliability and willingness to promptly address any concerns have made them a trusted choice for both roof replacements and insurance claim work in the local community.
"I highly recommend Monarch Roofing. From the first call to the final walkthrough, the experience was smooth and professional. They were easy to work with and very responsive—communication was excellent throughout the project. They showed up when they said they would, kept the job site neat and safe, and the cleanup at the end was thorough. The pricing was also very competitive, and they were transparent about what was included. I especially…" — Pat B.
+1 410-541-5383
Chesco Remodeling earns consistent praise from customers for exceptional communication, with team members like Nick providing daily updates and remaining available throughout projects. Clients appreciate the company's skilled craftsmanship, reliability in meeting deadlines, and ability to handle scope changes seamlessly—from roof repairs and window installation to kitchen and bathroom remodels. The team's professionalism and genuine care for customer satisfaction set them apart, with customers noting they go above and beyond to ensure quality work and a stress-free experience.
"In October 2025, I chose Chesco Remodeling, LLC to install a new dual-fuel range and hood I purchased (which needed to be vented outside). As our conversations about the upcoming work progressed I spoke to Nick and Ramona about other work I was considering including new countertops and backsplash. They gave me great suggestions, which I went with, and agreed to expand the scope of work and the mini remodel of my kitchen began. From the…" — PC M.
+1 443-710-9133
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.