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Best Roofing Contractors in Cheswold, DE
Looking for a roofer in Cheswold? We list 2 roofing contractors based in Cheswold, Kent County, with ratings, phone numbers, addresses and services side by side. Roofing & Siding Specialist currently ranks first, with 5.0 stars from 17 Google reviews. Most homes around Cheswold have asphalt shingle roofs, while farms and outbuildings often use metal, so ask whether a roofer handles both before you book an inspection. Roofers based in nearby Leipsic (4 mi) and Dover (5 mi) also regularly work in Cheswold. Always confirm a roofer's Delaware business license and insurance before signing a contract.
2 roofers4.6 average rating21 reviews1 open on Saturdays
Featured roofers in Cheswold
Paid placements, always labelled. They never change the ranked order below.
Featured
This spot is open
Put your roofing company here, in front of every homeowner looking for a roofer in Cheswold. Paid placements are always labelled and never change the ranked order.
Ask about featuringPut your company first on the Cheswold page
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★ 5.0 · 17(302) 653-0524View profile
CC★ 3.0 · 4
(302) 505-0260View profile
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Listings compiled from public Google Maps profiles and business listings, last updated 2026-10-20.
Frequently asked questions
How many roofing contractors are there in Cheswold, DE?
We list 2 roofing contractors based in Cheswold, Kent County. 2 of them have Google reviews. Roofers in nearby Leipsic and Dover also work in Cheswold.
Who are the best roofers in Cheswold?
By review-weighted rating, the top 2 are Roofing & Siding Specialist (5.0★ from 17 reviews) and Carvers Construction LLC (3.0★ from 4 reviews). The score rewards a high rating backed by many reviews, so a 5.0 from a handful of reviews doesn't automatically come first.
What roofing services do Cheswold roofers offer?
Of the 2 roofers listed in Cheswold, 1 mentions roof replacement, 1 mentions roof & leak repair, 1 mentions asphalt shingle, 1 mentions metal roofing and 1 mentions gutters & leaf guards. Use the service filters above the list to narrow it down, and confirm with the roofer before booking.
Are Cheswold roofers open on weekends?
2 of the 2 roofers in Cheswold list their hours. The most common weekday hours are 8AM–5PM. 1 roofer is open on Saturdays. Each profile shows full hours and an open-now badge.
Do I need a permit to replace a roof in Cheswold?
Usually, yes. Most roof replacements in Delaware need a building permit, while small repairs often don't. Rules differ between towns, so check with the Town of Cheswold or Kent County. A reputable roofer pulls the permit for you; be wary of anyone who asks you to do it.
How should I compare roofing quotes in Cheswold?
Get two or three written quotes from Cheswold-area roofers and compare them line by line: tear-off or overlay, the shingle or metal product, underlayment, ice and water shield, flashing, ventilation, decking repairs (price per sheet), disposal, and both the manufacturer and workmanship warranties. The cheapest total often leaves one of these out.
When is the best time to replace a roof in Cheswold?
Late spring through fall is the busiest season, because asphalt shingles seal best above about 40°F. Winter is quieter, and roofers can often schedule you sooner if the weather allows. After a big storm, expect waits while roofers handle emergency repairs first.
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