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TRUSTED BY SOUTHOLD, NY HOMEOWNERS

  • Average homeowner rating star icon4.7
    Average homeowner rating
  • Verified reviews icon173
    Verified roofing services reviews

Find Roofers in Southold

Avatar for Four Seasons Roofing
Four Seasons Roofing
4.6(
150
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair+26 more

Serving Southold, NY and surrounding areas

Approved

In business since 1983

Free estimates

Emergency services offered

"My entire roof was redone in one day!. Four seasons staff are true professionals, they had a crew of 20 people working from 7:00 am till about 5:00 p.m. They arrived fully equipped and worked until roof was completed. The following day the Gutters were installed and voila!, my roof was completed and my yard was cleaned as if nothing happened. Professional service. Very happy with the service provided by Four Seasons."
GAF Preferred Contractor Badge
Additional Photos
Additional Photos
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Additional Photos

+19

Response time2 days
Response rate100%
11 neighbors recently requested a quote
Avatar for Rapid Roofing
Rapid Roofing
5.0(
19
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair

Serving Southold, NY and surrounding areas

Approved

Super Service Award Winner

In business since 2018

Free estimates

Warranties offered

"I had 3 layers of roofing on my house, and over the last 2 years I spent a ton of money on repairs. Finally I called Rapid Roofing and when they assessed the roof, they let me know that the reason I was having so many leaks was from the 3 layers of roofing and not having a proper roofing system. I decided to do a full roof replacement and it was the best decision I could have made because my roof looks great, my electric bill went down, and now I don?t need to keep repairing it! Awesome communication, great people and I got a great price! Bravo Rapid Roofing!"
Asphalt Shingle Roofs
Asphalt Shingle Roofs
Asphalt Shingle Roofs
Asphalt Shingle Roofs
Asphalt Shingle Roofs

+54

Response time7 hrs
Response rate94%
59 neighbors recently requested a quote
Express Way Roofing and Chimney, Inc.
4.8(
239
)
Asphalt Shingle Roofing - Install or ReplaceFlat, Foam, or Single Ply Roofing - Install or ReplaceMetal Roofing - Install or Replace+3 more

Serving Southold, NY and surrounding areas

Approved

In business since 2010

Free estimates

Credit card accepted

"Express Way Roofing is amazing his crew are fantastic the windows are beautiful and the roofing shingles are guaranteed for twenty years. I highly recommend Them"
22 neighbors recently requested a quote
Recommended by98%of homeowners
Avatar for Best Way Roofing & Chimney
Best Way Roofing & Chimney
4.9(
14
)
Inspection - RoofingAsphalt Shingle Roofing - RepairFlat, Foam or Single Ply Roofing - Repair+12 more

Serving Southold, NY and surrounding areas

Approved

In business since 2012

Free estimates

Emergency services offered

At Best Way Roofing and Chimney, we take pride in protecting and improving homes across Suffolk County and surrounding areas with top-quality roofing, chimney, and exterior services. With years of hands-on experience, our skilled team delivers reliable workmanship, honest solutions, and lasting results for every project.\nWe specialize in roofing installation, repair, and replacement, as well as chimney repair, cleaning, and rebuilding. Beyond roofs and chimneys, we handle all types of exterior work, including siding, gutters, masonry, and waterproofing, ensuring your home is both beautiful and well-protected year-round.\nWhether you’re dealing with storm damage, routine maintenance, or planning a full upgrade, Best Way Roofing and Chimney is committed to providing professional service at competitive rates. We’re fully licensed and insured, and every job is backed by our dedication to quality and customer satisfaction\nWe are here to keep your home safe, strong, and looking its best.\n\n

Response time5 hrs
Response rate95%
86 neighbors recently requested a quote
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Roofing questions, answered by experts

Roofing felt is the most common type of roof underlayment, likely because it has been around the longest. It’s called roofing felt because it is often made of felt soaked in asphalt. Depending on the type of roofing a home has, roofing felt comes in different thicknesses. 

If properly installed and maintained, roofing felt should last between 10 and 25 years. 

Tile roofing is durable, fire-resistant, and energy-efficient. It also adds aesthetic appeal and, with proper maintenance, can last 50-100 years.

Metal roofs last for between 50 and 70 years, and asphalt roofs last for between 20 and 25 years, with some lasting as long as 30 years. In most cases, you’ll get double the life or more out of a metal roof than you would from a shingle roof, which helps make the higher cost of a metal roof more manageable.

Here are a few tips on how to choose a roofer:

  • Get everything in writing

  • Ask for insurance, license, and bond, then verify them

  • Check their reviews 

  • Ask for recommendations

  • Get multiple quotes

You’ll also want to watch out for any red flags like:

  • Pushy sales tactics

  • Not willing to show necessary documentation

  • Bad gut instincts

Though cedar shakes often get confused with shingles, there are a few key differences between wood shakes and wood shingles. For one, cedar shingle prices are lower, although shingles are less durable than wood shakes. Cedar shakes are thicker than shingles (shingles range from about 3/8 to 1/2 inches thick, compared to 1/2 to 3/4 inches thick for shakes). Wood shakes are handmade, while shingles are usually machine-made. Also, wood shakes work better on steeper roofs than shingles do. While the cost of cedar shingles is more budget-friendly, there are many great reasons to choose shakes.

The Southold, NY homeowners’ guide to roofing services

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