Top-rated roofers.

Get matched with top roofers in Chestertown, MD

Enter your zip and get matched with up to 5 pros

Need a pro for your roofing project in Chestertown, MD?

Select your specific project to find the pro for you.

TRUSTED BY CHESTERTOWN, MD HOMEOWNERS

  • Average homeowner rating star icon4.5
    Average homeowner rating
  • Verified reviews icon125
    Verified roofing services reviews

Find Roofers in Chestertown

Avatar for Spicer Bros. Construction Inc.
Spicer Bros. Construction Inc.
4.6(
78
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairMetal Roofing - Install or Replace+26 more

Serving Chestertown, MD and surrounding areas

Approved

In business since 2002

Free estimates

Warranties offered

"I was really impressed with the experience working with Spicer Brothers for a new roof on a home built in 1994 that has hardly seen any improvements. Every step from the estimator through the installation went smoothly. When I met Dwayne on the job he was friendly, informative and helpful. His crew worked steadily and were finished well ahead of the estimated completion time. The new roof looks great and knowing the materials and workmanship that went into the installation I know I can rest easy for years to come."
Additional Photos
A sleek new shower with white simulated tile walls and chrome fixtures.
Additional Photos
Additional Photos
A beautiful new walk in shower installed with grab bars, shelves, a shower seat, and stylish black fixtures.

+9

41 neighbors recently requested a quote
Recommended by92%of homeowners
Avatar for New Castle Constructs, LLC
New Castle Constructs, LLC
4.9(
31
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Repair - For BusinessFlat, Foam or Single Ply Roofing - Repair+2 more

Serving Chestertown, MD and surrounding areas

Approved

In business since 2023

Free estimates

Credit card accepted

New Castle Constructs is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers' interests, and make their concerns the basis of our business.

Roof Replacement
Roof Replacement
Roof Replacement
2 neighbors recently requested a quote
Recommended by83%of homeowners
AML Top Quality Construction
4.6(
27
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair

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 time1 day
6 neighbors recently requested a quote
Recommended by70%of homeowners
...
Showing 1-10 of 292
Roofing questions, answered by experts

Using a staple gun to hang Christmas lights on your roof or shingles is not recommended. Puncturing your roof with staples can cause damage, leading to cracks, leaks, and exposure to the elements. Staples are also less reliable than other methods like roof clips. For a safer alternative that won't damage your roof, use shingle tabs.

A roof replacement will usually include removal of your old roof, shingle replacement, and a new roof underlayment, but it may only include adding new shingles if you’re layering new shingles over the old shingles. If you have signs of roof leaks or your roofer finds water damage to the roof decking underneath your old roof, it can also include replacement of the OSB or plywood decking that lays over your rafters and supports the roofing material above.

Whether replacing the entire roof or just installing roof shingle replacements in small areas, always pull up the old roof shingles. While you can technically put new roof shingles (but not other roof materials) over old shingles, this can add weight strain to the roof and prevent the new shingles from securing properly to the roof.

If your home doesn't have gutters, you can still hang Christmas lights on the roof using specialized clips. Use roof clips designed to attach to shingles or fascia. For tile roofs or the edges of the rooftop, consider using parrot clips. Adhesive light-hanging clips are also a great option. It's important to avoid using nails or staples, as they can damage your roofing material. For unique or complex installations, it's best to consult a professional Christmas light installer to find the safest and most effective solution for your home.

If a roof is not vented, trapped air and moisture have nowhere to go and will cause moisture to build up in the attic. When moisture builds up, it can cause mold and mildew, leaks, and rot. It will make the space hot and stuffy, which can result in higher energy bills as the HVAC system works overtime to regulate the temperature.

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.