Chestertown Roof Replacement Cost:
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How Much Does a New Roof Cost in Chestertown, Maryland in 2025?
Understanding the cost of a roof replacement in Chestertown can be confusing. Prices depend on the size and complexity of your roof, the materials you choose, and local labor rates.
While every home is unique, we've gathered data to provide a general cost overview for the Chestertown market. However, for a price tailored to your specific home, you must use our free AI estimation tool.
| Roofing Material | Average Cost / Sq. Ft. (in Chestertown) | Estimated Cost for 2,000 sq. ft. Home |
|---|---|---|
| Asphalt Shingles |
$5.50 - $35.00
|
$11,000 - $70,000 |
| Metal Roofing |
$14.50 - $35.00
|
$29,000 - $70,000 |
| Flat Roofing |
$9.00 - $35.00
|
$18,000 - $70,000 |
| Tile Roofing |
$35.00
|
$70,000 |
| Cedar Shake |
$15.00 - $35.00
|
$30,000 - $70,000 |
| Other Materials |
$14.00 - $35.00
|
$28,000 - $70,000 |
| Roof Repair |
Flat Rate
|
$5 - $899 |
Disclaimer: These are based on RoofHero's proprietary database of roofing contractor pricing in the Chestertown, Maryland area and are for informational purposes only. Use our AI tool for a precise quote based on your roof's actual measurements.
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HOW IT WORKS
Instant Roof Estimate & Pro Matching
Quick Online Experience
RoofHero is a search engine for pre-vetted roofing companies in the United States with built-in instant roof estimates. Our algorithm measures your roof in 3 seconds, filters out candidate roofing companies based on how you answer our questionnaire, and selects a single vetted roofing company that meets your criteria.
Real Prices
You will get a real price online from your matched pro specific to your roof's surface area and material. Our database holds their material-specific roof replacement and roof repair pricing. Combining the instant measurement of your roof and a pre-selected roofer's pricing generates your custom roof estimate.
Vetted Roofing Companies
RoofHero Pros are vetted individually with a real person from RoofHero's team. We ensure they provide high-quality workmanship and materials, compare their pricing with market pricing in your area, and ensure their team is set up to serve you well.
Proprietary AI
Our propriety AI algorithm will measure your roof from a satellite image of your home in real time. In addition to using AI to measure your roof, we use AI to select the best roofing company in your zip code, combined with robust logic applied to your selections.
Built By Professionals
The team that built this site is comprised of highly technical staff, including machine learning engineers, software engineers, data scientists, and roofing business owners. We believe this website is the easiest, most transparent, and most authoritative way to find the right roofing company and get a real roof estimate fast.
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Type your address above and answer a few questions about your roof. This takes less than 30 seconds to complete.
Complete Roofing Services for Chestertown Homes
Our network of certified Chestertown roofing professionals handles all types of projects, ensuring your home is protected from Maryland's unpredictable weather.
Roof Repair & Leak Detection in Chestertown
Don't let a small leak turn into a major problem. From missing shingles after a thunderstorm to tracking down hard-to-find leaks, our partnered pros offer fast and reliable roof repair services across the Chestertown area.
Full Roof Replacement
When it's time for a new roof in Chestertown, get it done right. Use our custom roofing company search engine (above) to get an accurate budget, and our vetted local contractors ensure a high-quality installation with top-tier materials designed to last.
Storm & Hail Damage Restoration
Maryland storms can be unforgiving. If your roof has suffered wind or hail damage, our vetted pros can help guide you through the process, from initial damage assessment to a full restoration.
Verified & Vetted Local Roofers Serving Chestertown, Maryland
We don't work with just anyone. Every roofing company in our Chestertown network is required to be licensed, insured, and have a proven track record of quality craftsmanship and customer satisfaction.
Chestertown Roofing FAQs
What should I look for in a roofing contractor in Chestertown?
When choosing a roofer in Chestertown, verify they are licensed, insured, have local references, and offer warranties. All RoofHero vetted contractors meet these standards and have proven track records of quality work.
Can I install a new roof over my existing roof in Chestertown?
While it's sometimes possible to install a new roof over an existing one, it's generally recommended to remove the old roof first. This allows for proper inspection of the decking and ensures proper installation of the new roof.
Do I need to be home during the roof replacement in Chestertown?
You don't need to be home the entire time, but it's recommended you be available at the start and end of each work day. Your contractor will coordinate access and keep you updated on progress.
What is the warranty on a new roof in Chestertown?
Warranty coverage varies by material and contractor. Most roofing materials come with manufacturer warranties of 20-50 years, and contractors typically offer workmanship warranties. Your RoofHero contractor will explain all warranty details.
How do I know if my roof has hail damage?
After a hailstorm in Chestertown, look for dents or "bruising" on shingles, cracked fiberglass, and an excessive amount of granules in your gutters. If you suspect damage, it's best to get a professional inspection.
What roofing material is best for the climate in Maryland?
Architectural shingles are a popular and cost-effective choice, offering excellent durability against the heat and humidity common in Chestertown. Metal roofing is also a fantastic option for superior longevity and energy efficiency.
How do I prepare my home for a roof replacement in Chestertown?
Before roof replacement in Chestertown, clear your yard of vehicles and outdoor furniture, protect landscaping, and secure valuables in your attic. Your contractor will provide specific preparation instructions.
Can I get a roof replacement in the winter in Maryland?
Yes, roof replacements can be done in winter months in Maryland, though weather conditions may affect scheduling. Our vetted contractors are experienced working in various weather conditions and will ensure proper installation.
How long does a typical roof replacement take in Chestertown?
Most roof replacements in Chestertown take 1-3 days depending on the size and complexity of your roof. Weather conditions can also affect the timeline, but your contractor will keep you informed throughout the process.
What happens to my old roof materials after replacement in Chestertown?
Your roofing contractor will handle disposal of all old roofing materials. They typically use a dumpster and ensure all materials are properly disposed of according to local regulations in Chestertown.
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Top Roofing Companies in Chestertown, Maryland
Use our custom roofing company search engine (above) to filter for your exact criteria to ensure we match you with the right roofing company in Chestertown. A list of top roofing companies are listed below.
Roofer Hotline
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Call: 629-206-6498
| Website | Rating | Phone | Address |
|---|---|---|---|
| Monarch Roofing | 5 | (410) 541-5383 | 205 Canal St, Grasonville, MD 21638 |
| ALP Roofing | 5 | (410) 600-7663 | 1716 Harford Rd Suite 201, Fallston, MD 21047 |
| Top Quality Remodeling & Restoration | 5 | (410) 844-3111 | 2617 E Rhododendron Dr, Abingdon, MD 21009 |
| Maryland Elite Exteriors | 5 | (410) 304-2048 | 610 B 4-H Park Rd, Queenstown, MD 21658 |
| Angelo and Son Roofing | 5 | (410) 652-1819 | 1010 State Hwy 755, Edgewood, MD 21040 |
| Rollins & Associates Inc. | 5 | (443) 807-3093 | 11716 Hamilton Pl, White Marsh, MD 21162 |
| Paddy's Roofing, Siding and Chimneys | 4.9 | (302) 314-7663 | 5207 Summit Bridge Rd, Middletown, DE 19709 |
| G J Goss Contracting Inc | 4.8 | (410) 538-5680 | 1115 Clayton Rd, Joppatowne, MD 21085 |
| Canales Service LLC | 4.8 | (410) 705-0533 | 4222 Main St, Grasonville, MD 21638 |
| Amazing Home Contractors | 4.7 | (410) 690-4990 | 2102 Old Orems Rd, Middle River, MD 21220 |
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