Top-rated roofers.

Get matched with top roofers in Chestertown, MD

Enter your zip and get matched with up to 3 pros

Matching on HomeAdvisor

Share some details icon
Share some details about your home project.
Match with local pros icon
Within moments, match with highly-rated local pros.
Compare quotes icon
Compare quotes and choose the best pro for the job.

Top-Rated Roofers in Chestertown - Updated Nov 2026

Avatar for Roofing Pups, Roofing & Siding
Roofing Pups, Roofing & Siding
4.7(
74
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairMetal Roofing - Install or Replace+1 more

Serving Chestertown, MD and surrounding areas

Approved (Corporate)

Super Service Award Winner

In business since 1994

Free estimates

Credit card accepted

"There's nothing worse that dealing with pooring rain and strong winds and then hearing the drip, drip sound of water coming into your home due to a damaged roof. I reached out to roofing repair companies through Angie's list and Roofing Pups responded. Marcus came out the next day and put my fears at ease. The bad news was that I needed a new roof. He showed me my options available, categorized as "good", "better" and "best". Despite my choosing the lowest option, he still threw in some discounts and upgrades at no additional cost. I signed the contract and he arranged for someone to come out at tarp my roof. He even went the extra mile of going to Home Depot and setting up buckets in my attic to catch the water still coming in. The roofing crew came out two days later and gave me a beautiful new roof. They then meticulously cleaned the area. It was great working with Roofing Pups. I couldn't be happier and highly recommend!"
Roof Install
ROOFING PUPS
ROOFING PUPS
ROOFING PUPS
PROJECTS

+4

Response time1 day
Response rate93%
173 neighbors recently requested a quote
Avatar for Home Genius Exteriors
Home Genius Exteriors
4.9(
388
)
Asphalt Shingle Roofing - Install or Replace

Serving Chestertown, MD and surrounding areas

Approved

In business since 2004

Free estimates

Emergency services offered

Elevate your home with Home Genius Exteriors, setting the standard by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It?s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!

Asphalt Roofing
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing

+76

Recommended by96%of homeowners
AML Top Quality Construction
4.6(
27
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Install or Replace

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 2009

Free estimates

Emergency services offered

"Casey and his crew have been my go-to team over the last 10years and on several projects, from complete rehabs from roofing. soffits and fascia, outside, to the new kitchen and baths inside! My wife especially LOVES the screened -in porch they added on to our family home, and she's fussy about the quality of work to say the least. They have traveled far and wide across the Eastern Shore and even rehabbed a rental for me in Dover! Good work is hard to find nowadays, but Casey and crew clean up after themselves daily, and most importantly are REASONABLE in their rates !"
Response time2 days
6 neighbors recently requested a quote
Recommended by70%of homeowners
Avatar for Economy Restoration, LLC DBA Economy Roofing & Restoration
Economy Restoration, LLC DBA Economy Roofing & Restoration
4.3(
35
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Repair - For Business

Serving Chestertown, MD and surrounding areas

Approved

In business since 2018

Free estimates

Emergency services offered

"Jordan Taylor was our rep and did an outstanding of explaining the entire process to us, including how to submit the roof replacement to insurance due to a wind storm. He was super responsive for every question, and he personally got our HOA approval, then walked it through the town govt to get the permit! On the day of installation, his team worked efficiently and quickly, and our roof was completed by late afternoon, including full and thorough cleanup. Jordan came back the next day to walk the property to make sure all garbage was picked up. Economy Restoration will also provide a Quality Control person to go up on the roof for the final inspection, which really gives us a secure feeling. Our roof is amazing, along with the entire process and the pricing is very fair. I highly recommend Jordan and Economy Restoration!"
Roof Replacement During Install
Finished Product
Chimney Flashing
Chimney & Step Flashing
Rear Elevation Finished Product

+3

Response time1 day
Response rate90%
78 neighbors recently requested a quote
...
Showing 1-10 of 219

FAQs for roofing projects in Chestertown, MD

Maintaining your soffit is essential. You must inspect it twice yearly to catch any clear signs of deterioration. Look for cracks, mold, rotted wood, sagging sections, chipped paint, or missing boards. If these issues are detected, contact a professional immediately to repair or replace the damaged soffit and protect your home’s structural integrity.

To maintain your fascia boards and soffits, inspect them regularly to protect your roof and home's structure. Clean your gutters to remove debris and prevent moisture buildup. Repaint any damaged sections to keep moisture at bay. Upgrading drip edges and vents improves airflow and dispels moisture efficiently, helping you avoid severe damage and costly repairs.

While installing a new soffit over an existing soffit isn't common, it may be necessary in some older homes. If removing the original soffit could damage delicate structures, a professional might recommend installing the new soffit without complete removal. Always consult a qualified professional to assess the condition and ensure this method is safe and effective.

When hiring someone for soffit and fascia repair, choose a specialist with proven roofing and gutter systems expertise. A knowledgeable contractor will thoroughly inspect your home and provide a straightforward repair or replacement plan. Check online reviews and ask for references to ensure you receive high-quality service that delivers lasting results and strong protection for your home.

The Chestertown, MD homeowners’ guide to roofing services

From average costs to expert advice, get all the answers you need to get your job done.