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

Top-Rated Roofers in Southold - Updated Nov 2026

Avatar for Rapid Roofing
Rapid Roofing
5.0(
31
)
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%
91 neighbors recently requested a quote
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
Additional Photos
Additional Photos

+19

Response time2 days
Response rate100%
15 neighbors recently requested a quote
Express Way Roofing and Chimney, Inc.
4.8(
239
)
Asphalt Shingle Roofing - Install or ReplaceNatural Slate 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"
16 neighbors recently requested a quote
Recommended by98%of homeowners
Avatar for ABC Roofing
ABC Roofing
4.9(
84
)
Asphalt Shingle Roofing - RepairFlat, Foam or Single Ply Roofing - RepairWood Shake or Composite Roofing - Repair

Serving Southold, NY and surrounding areas

Approved

In business since 2013

Free estimates

Emergency services offered

"I would highly recommend them. They fixed a leaking roof for me. They were available quickly for an estimate and to do the work. The price they gave was more than reasonable especially compared to other estimates. They work fast but accurate. Took pictures as they went along to show me. Clean up was perfect. Can't forget to mention the customer service was beyond great."
skylight
skylight
valley leak
valley leak
new roof

+13

Response time3 hrs
Response rate87%
17 neighbors recently requested a quote
Avatar for Best Way Roofing & Chimney
Best Way Roofing & Chimney
4.9(
14
)
Inspection - RoofingAsphalt Shingle Roofing - RepairSealant for Roof - Apply+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%
98 neighbors recently requested a quote
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Roofing FAQs, answered by experts

In some cases, yes, you can put a second roof layer over architectural shingles, but it depends on your home’s structural stability and the local building codes where you live. Architectural shingles are thicker and heavier than standard asphalt shingles, so you may need structural reinforcement or a structural engineer’s inspection before proceeding. Additionally, some building departments don’t allow for two roof layers, regardless of the roof type. You should ask a professional if ripping the old roof off before installing the new one is the best option for you.

Roll roofs don’t last as long as traditional roofs, like those made of asphalt shingles. A roll roof typically lasts between five and 15 years, whereas a shingled roof will last between 20 and 50  years. Modified bitumen roofs are similar in look to rolled roofing but have a 12 to 15 year warranty.

Architectural shingles typically last between 20 and 30 years, though most homeowners should plan on replacing them every 20 to 25 years. While some manufacturers offer warranties for 30 to 50 years, especially for extreme weather, achieving such a long lifespan is rare. The actual lifespan can be shorter in areas prone to strong winds, hailstorms, or other extreme weather. It is recommended to replace your roof before it reaches the end of its life to reduce the risk of roof failure, leaks, and costly property damage. Scheduling regular roof inspections will help you determine your roof's remaining life and identify the best timeline for replacement.

You can only overlay a roof once. Any additional layers of shingles will add too much weight and may also violate building codes. Once your roof has had an overlay, you’ll need to have a full roof replacement, including a tear-off of all existing roofing materials, when it’s time for a new roof. 

Moving a chimney is possible, but it is a very complex process that requires professional expertise, knowledge of building codes, and safety protocols. Most homeowners find it easier to remove the fireplace and build a new fireplace and chimney in the new location of your home. Talk to your chimney pro about all your options, their costs, and pros and cons. 

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.