Free Estimate 📞 (877) 586-1316 24/7
Professional Roofing hero
โ˜…โ˜…โ˜…โ˜…โ˜… 4.7/5 from 446+ reviews

Local Southold Roofing Contractor. Free Estimates

Hail damage? Missing shingles? Call (877) 586-1316 today. Free roof inspection and insurance claim assistance in Southold. Free estimates, no pressure. Ever.

19+
Years
500+
Projects
4.7
Rating
19+
Years Experience
500+
Projects Completed
4.7
Star Rating (446+ Reviews)
โœ“
Licensed & Insured

Our Services

Our Roofing Services

Full-service roofing contractor in Southold โ€” from asphalt shingle roof replacement and emergency hail damage repair to metal roofing, flat roof systems, and gutter installation. Every project is installed by manufacturer-certified crews with workmanship warranties.

roof replacement
FREE ESTIMATE

Roof Replacement

We don't do shortcuts on replacements. Tear off the old roof, check the decking for soft spots, install synthetic underlayment, drip edge, starter strip, shingles, ridge vent. The whole system. Your roof is only as good as the layers underneath.

roof repair
SAME-DAY

Roof Repair

Roof repairs get worse when you ignore them. A $400 flashing repair turns into $4,000 of water damage inside the wall. Our Southold crew can usually get there within 48 hours for non-emergency repairs.

storm damage repair
LICENSED

Storm Damage Repair

Wind damage doesn't always look obvious from the ground. Lifted shingles, broken seals, exposed nail heads. You can't see any of that without getting on the roof. Our Southold inspector does a full 27-point inspection, free of charge.

new roof installation
TOP RATED

New Roof Installation

New construction or an addition? We install new roofing systems from scratch. Decking inspection, ice and water shield, synthetic underlayment, ventilation calculations, and whatever material you want on top. Shingles, metal, or flat.

metal roofing
GUARANTEED

Metal Roofing

We install 24-gauge and 26-gauge standing seam in Galvalume and pre-painted steel. Concealed fastener system means nothing's exposed to weather. Panels lock together at the seam and clip to the roof deck.

shingle roofing
INSURED

Shingle Roofing

GAF Timberline HDZ architectural shingles with StrikeZone nailing area. The highest-selling shingle in North America. Impact-rated to UL 2218 Class 4 when installed with the full GAF Roof System. Our Southold crews install Timberline in the full system configuration to qualify for Golden Pledge warranty. ASTM D3462 and D7158 Class H certified.

flat roofing
FREE ESTIMATE

Flat Roofing

A flat roof that's ponding water is a flat roof with a problem. We install tapered insulation systems to create positive drainage to your scuppers or interior drains. No more standing water after rain.

commercial roofing
SAME-DAY

Commercial Roofing

Flat roofs on commercial buildings are a different animal. We install and repair TPO, EPDM, modified bitumen, and built-up systems. Our Southold commercial crew handles retail, warehouse, office, and multi-family buildings.

gutter installation
LICENSED

Gutter Installation

Gutter replacement in Southold runs $8-$15 per linear foot installed, depending on material and story height. That includes hangers every 24 inches, end caps, miters, and outlet drops. We custom-form everything on-site.

roof inspection
TOP RATED

Roof Inspection

We climb up, walk the entire roof, and document what we find with photos and measurements. Takes about 30 minutes. You see exactly what we see. No mysteries, no scare tactics.

emergency roof repair
GUARANTEED

Emergency Roof Repair

After we tarp and secure your roof, we document everything for insurance purposes. Photos, measurements, damage descriptions. Your adjuster gets a professional report, not a handwritten note.

skylight installation
INSURED

Skylight Installation

A skylight installed wrong will leak. The flashing has to integrate with the shingle courses. Step flashing on the sides, headwall flashing on top, and a sill pan underneath. We use manufacturer flashing kits because they're engineered to work with the skylight frame.

Why Choose Southold Roofing & Maintenance?

Trusted by homeowners and businesses across Southold.

Financing Available

A new roof is a big expense. We offer 12-month same-as-cash and low-interest financing through GreenSky and Hearth. Get your roof done now, pay over time.

4.7-Star Google Rating

446+ homeowners reviewed us. We don't pay for reviews or offer discounts for them. Those are real people who hired us and took the time to say we did a good job.

Manufacturer Certified

GAF Master Elite, Owens Corning Preferred, CertainTeed SELECT ShingleMaster. We carry certifications from the big three. That means factory-trained crews and the best available warranties.

Insurance Claims Handled

Storm damage? We work with your insurance company directly. Free inspection, Xactimate documentation, adjuster meeting on-site. We fight for full replacement when your roof qualifies.

Our Work

Recent Projects

roof replacement project

Roof Replacement

Southold, NY

roof repair project

Roof Repair

Southold, NY

storm damage repair project

Storm Damage Repair

Southold, NY

View All Projects โ†’

Simple Process

How It Works

1

Roof Evaluation

Call (877) 586-1316 and we'll schedule an inspection at your convenience. Our Southold inspector checks every detail. Shingles, flashing, vents, gutters, decking condition.

2

Written Estimate

Multiple material options at different price points so you can compare. GAF, Owens Corning, CertainTeed. We install all three and let you pick what fits your budget.

3

Professional Crew

No subcontractors. Our crews, our equipment, our supervision. A project manager checks in throughout the day and does a final quality inspection before cleanup.

4

Quality Check

We walk the property with you, show you the finished roof, answer any questions. Then we run the magnetic nail sweep and clean up every scrap of debris.

Verified Reviews

What Our Customers Say

โ˜…โ˜…โ˜…โ˜…โ˜… 4.7/5 from 446+ reviews
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"Our roof was 22 years old and starting to curl. They did a full tear-off and installed Timberline HDZ in Weathered Wood. Looks incredible. Crew was fast and cleaned up everything."

J
Jennifer B.
Southold
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"Needed emergency tarping after a tree hit our roof. They were there in about 3 hours. On a Saturday. Tarped the whole section, removed the branch, and had a crew out Monday morning for the repair."

K
Kevin H.
Southold
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"Had a huge oak branch go through the roof during a storm. Southold Roofing & Maintenance tarped it the same night and had the repair done two days later. Insurance covered everything and they handled the whole claim."

S
Steve W.
Southold

Service Areas

Areas We Serve

From Southold to Far Rockaway, Hancock, Kingston, Middle Granville, Ocean Beach. We've replaced roofs on every street. Ask your neighbor. Chances are we did theirs.

Far Rockaway Hancock Kingston Middle Granville Ocean Beach Ravena Slate Hill Verona Yorkville Boiceville
D

Meet the Owner

David Carter

Owner & Lead Contractor

David has been serving Southold for over 19 years, building a reputation on honest work, fair pricing, and crews that treat every home like their own. What started as a one-truck operation has grown into a full-service Roofing company โ€” but the values haven't changed.

"We don't cut corners. Every job gets the same attention to detail whether it's a small repair or a complete replacement. That's how you earn 446+ five-star reviews."

License #1222123 19+ Years Experience Locally Owned & Operated

FAQ

Frequently Asked Questions

Common signs: curling or cracking shingles, missing shingles after wind events, granule loss (look in your gutters), daylight visible through the attic, sagging roof deck, and age. Most asphalt roofs last 20-30 years in New York. If you see any of these, call (877) 586-1316 for a free inspection. We'll be honest about whether you need a replacement or just a repair.

We partner with GreenSky and Hearth for roofing financing. Options include 12-month same-as-cash (0% if paid in full within 12 months), 5-year fixed rate, and 7-10 year extended plans. Monthly payments on a $15,000 roof run about $150-$250/month depending on the term. Apply during the estimate.

You get two warranties: one from the manufacturer on the materials and one from us on the workmanship. As a GAF Master Elite contractor, we can offer the Golden Pledge. That's 25 years on workmanship plus 50 years on the shingle. Owens Corning and CertainTeed have similar programs. Our own workmanship warranty is in writing and covers installation defects.

Yes. We handle insurance claims regularly. It's a big part of what we do in Southold. Free inspection, photo documentation, claim filing assistance, and we meet the adjuster on-site. If the claim is approved, we do the work at the insurance-approved price. You pay your deductible and we handle the rest.

Most residential roofs in Southold are done in one day. We show up at 7 AM, tear off the old roof, install the new system, and clean up by end of day. Two-story homes, steep pitches, or large roofs might take two days. We never leave a house uncovered overnight.

Have more questions? Call (877) 586-1316

SAME-DAY APPOINTMENTS AVAILABLE

Get Your Free Roof Inspection Today

24/7 emergency service. Most appointments available within 48 hours.

📞 Call (877) 586-1316

โ˜…โ˜…โ˜…โ˜…โ˜… 4.7/5 from 446+ Reviews  ยท  Licensed  ยท  Insured