Best Roofing Companies Near You in Chestertown, MD (2026)
Top Roofers in Chestertown, MD
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Excel Roofing earns consistent praise for exceptional communication and professionalism throughout every project stage, with customers highlighting the attentiveness of team members like Ben and Will who keep clients informed and involved. The company is recognized for superior workmanship and thoughtful solutions, including product recommendations, insurance claim assistance, and attention to detail—even on complex architectural features—that consistently exceed customer expectations. Customers appreciate the company's efficiency, reliability, and genuine care for their work, resulting in strong recommendations and repeat business from satisfied clients.
"I highly recommend Excel Roofing from start to finish on a new roof. I unfortunately had to replace a roof that was on my home after 18 months due to a manufacturing defect (different contractor/product line than Excel). Noone plans to re-do a roof in such a short amount of time. I had Excel come out an evaluate the project, give product recommendations, plan to fix some items that original contractor did not address and give appropriate pricing.…" — Anthony S.
+1 443-819-3017
Clearview Home Remodeling earns consistent praise from customers for their exceptional professionalism, attention to detail, and commitment to quality craftsmanship across roofing, remodeling, and home improvement projects. Clients particularly appreciate the team's reliable communication, prompt completion of work, and fair pricing, with many noting that the entire process feels smooth and stress-free from start to finish. The company's skilled team members are frequently highlighted by name for their expertise and friendly demeanor, making homeowners feel confident and supported throughout their projects.
"Clearview Home and Remodeling is absolutely amazing! Alex, Scott, and the entire team are wonderful to work with. They are extremely professional, pay close attention to every detail, and complete the job quickly without sacrificing quality. Our project was done to perfection, and the entire process was smooth and stress-free from start to finish. I highly recommend Clearview Home and Remodeling to anyone looking for high-quality work—whether…" — Anastasia M.
+1 410-882-2222
TSW Roofing Solutions Inc
TSW Roofing consistently earns praise for Brandon's honest, detailed communication and transparent approach to estimates, with customers appreciating that he takes time to explain issues and provide multiple solution options. The team is recognized for professional, meticulous workmanship—from initial inspections to thorough cleanups—and their responsiveness in scheduling and addressing customer questions. Customers highlight the company's reliability and durability of work, with one client confirming the integrity of repairs made years earlier after severe winter weather.
"I found myself in a difficult and unexpected situation when we learned we needed a roof replacement on our new home. Of all the roofers I spoke with, Brandon was easily the most forthcoming and realistic about the work needed and the cost. He gave me a great quote and sent me an email explaining everything. He was easy to get in touch with for any questions and worked with us to get on the schedule asap. His team was polite, professional, and…" — Michael B.
+1 410-979-7876
Roof Right consistently earns five-star reviews for its professionalism, responsiveness, and attention to detail. Customers praise the team's promptness—from same-day or next-day estimates to completing work ahead of schedule—and their thorough, courteous approach to inspections and explanations of needed repairs. The company's willingness to go above and beyond, such as offering complimentary services and delivering high-quality results, builds lasting customer loyalty and confidence in their work.
"We called Roof Right for a quote on getting a gutter and downspout installed on my wife's potting barn. Roof Right had replaced our roof in 2022 and did a fantastic job, so we wanted to see if they could help us with this little job. Michael came right out the next day and took a look at what we wanted done, and got the estimate to us. We thought the cost was a little high, but that's to be expected today. Besides, it was really going to save…" — Mitch M.
+1 410-374-5923
Apple Remodeling earns consistent praise from customers for exceptional professionalism, clear communication, and meticulous attention to detail throughout the roofing process. Clients highlight the company's reliability in meeting timelines and budgets, transparent pricing with no hidden charges, and outstanding cleanup that leaves properties spotless. The team's expertise, friendly customer service from initial estimate through project completion, and commitment to quality workmanship make them a trusted choice for homeowners in the Carroll County area.
"I can tell you, Apple has been the best experience I have had with any home renovation company before. From the moment Katie took my call, they were attentive to what I needed and super friendly. She was there every step of the way to explain the business end of things and helped with the financing and warranty. Phil came out and I was impressed with both his knowledge of the roofing products they offer, as well as the up front honesty with the…" — GREG T.
+1 302-333-7395
Best Construction Inc. earns consistent praise for exceptional quality workmanship, responsive communication, and fair pricing on roofing and home improvement projects. Customers highlight the team's professionalism, reliability, and attentiveness—from immediate responses to inquiries to follow-up visits after project completion. Whether handling routine roof installations or complex structural damage repairs, Best Construction delivers outstanding results that exceed customer expectations.
"Thanks for the oppertunity to convey my satisfaction for both the roof and siding repair preformed on my house following a tree falling on my house. Structural damage was repaired as well as roof shingles and siding. Due to out of date siding Best suggested using the porch siding on the main house and placing new siding on the porcch. We are totaslly satisfied with roof and siding repair.There is no indication of any repair and the new siding on…" — Robert P.
+1 302-678-4749
Genesis Contracting and Home Improvements stands out for exceptional communication and professionalism throughout every project stage, with project manager KT consistently keeping customers informed of timelines and daily progress. Customers consistently praise the quality of workmanship, attention to detail, and the team's respectful, courteous approach to their homes—from major renovations to smaller custom jobs. The company is also recognized for honest assessments, fair pricing, and a willingness to take on projects other contractors decline, making them a reliable partner for both large remodels and unexpected home needs.
"Out of three contractors I contacted, Genesis was the only one who brought out a tape measure. The project manager asked questions and follow-up questions to make sure we were on the same page. When he was making up the contract, he gave me choices. There were three ways to approach the roof. He went over the process for each choice and the cost. My home is in a CHAPS neighborhood. Everything must meet specific requirements. The project manager…" — Mary C.
+1 443-982-4289
WS Contractors, led by owner Abe Wilcox, consistently delivers exceptional craftsmanship and attention to detail on roofing, siding, and remodeling projects, with customers praising the team's excellent communication, punctuality, and thorough cleanup. Clients particularly appreciate Abe's integrity, fair pricing, and transparent approach to estimates and project timelines, along with his hands-on supervision and ability to handle complex issues efficiently. The company has built a strong reputation for reliability, quality materials, and workmanship, with numerous customers returning for multiple projects and enthusiastically recommending them to others.
"We are very pleased to write this review on behalf of WS Contractors and Abe Wilcox in particular. Over the past few years, Abe has provided exceptional contractor services on several major projects at our home. He completed a basement remodeling that included a bathroom remodeling and created a beautiful bar area too. He and his team also recently completed a roof replacement for us. What makes Abe and company stand out is the commitment to…" — Craig J.
+1 410-688-1616
Ironshore Construction, led by owner Paul, earns consistent praise from customers for responsive communication, timely service, and high-quality workmanship across projects ranging from roofing and home repairs to snow and ice removal. Customers particularly value Paul's reliability—he returns calls and texts promptly, shows up as promised, and takes pride in treating properties with respect. With competitive pricing, licensed and insured credentials, and a track record of completing projects on time and within budget, Ironshore Construction is a trusted choice for homeowners in Kent County seeking dependable general contracting and home improvement services.
"I appreciate Paul with Ironshore Construction painting my garage and doing it with high quality! Paul also built a beautiful ramp for easy access from my garage to laundry room. In a day and age where it’s hard to get anyone to call you back answer a email, or respond to a text, Paul does. He takes pride in what he does. This is the second time I’ve used him. His prices are very reasonable, his work is excellent, and he treats your property with…" — Jimsatsea J.
+1 302-242-5144
Hammertime Construction earns consistent praise from customers for exceptional craftsmanship, attention to detail, and reliable project execution across roofing, decks, bathrooms, and porches. Owner John and his team are recognized for outstanding communication, punctuality, respectful on-site conduct, and daily cleanup, with customers noting that work is completed efficiently and often faster than anticipated. Clients particularly appreciate the combination of high-quality materials and skilled workmanship at competitive pricing, with multiple customers reporting results that exceeded expectations and expressing strong intent to hire the company for future projects.
"I absolutely love my new deck!! It ended up being a tear down of the old and starting all new instead of repairing the old deck i did a lot of research on decking materials since I have full sun on the back of my house. I chose timber tech boardwalk (as the color) I can walk around barefoot and not burn myself at all. Which is great especially since I have a dog that like to lay up here and sun him self. It is much cooler than the wood…" — Ximena O.
+1 443-298-1235
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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