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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
Additional Photos
Additional Photos

+19

Response time2 days
Response rate100%
11 neighbors recently requested a quote
Avatar for Rapid Roofing
Rapid Roofing
5.0(
20
)
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%
66 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"
18 neighbors recently requested a quote
Recommended by98%of homeowners
Avatar for O'Brien Brothers Contracting, Inc.
O'Brien Brothers Contracting, Inc.
4.9(
214
)
Asphalt Shingle Roofing - RepairInspection - RoofingFlat, Foam or Single Ply Roofing - Repair+10 more

Serving Southold, NY and surrounding areas

Approved

Super Service Award Winner

In business since 2015

Free estimates

Emergency services offered

"I was very pleased with O'Brien Brother's Contracting for a recent roof repair due to a leak. Eddie came the day that I contacted him. He was the fourth estimate that I received and proved to be very knowledgeable about the matter, including that the GAF shingle color that I have is no longer produced. That said, he was able to make some phone calls while standing on my roof and located a place with some remaining supply of the color shingle that is on my roof. The repair was quick and looks terrific. I will hire him again the next time I need a roof repair. Eddie also removed an old satellite dish and stump of an old electrical connection, and the roof looks great."
Copper flashings
Plywood
G.A.F Architectural shingles
Only the best materials
Chimney flashing and roof repairs

+53

Response time9 hrs
Response rate94%
61 neighbors recently requested a quote
Avatar for AAA Home Construction, Inc.
AAA Home Construction, Inc.
4.8(
142
)
Asphalt Shingle Roofing - RepairFlat, Foam or Single Ply Roofing - RepairAsphalt Shingle Roofing - Repair - For Business

Serving Southold, NY and surrounding areas

Approved

Super Service Award Winner

In business since 2018

Free estimates

Credit card accepted

"specific project was rebuilding chimney from roof up. Nice bunch of guys, extremely professional. I was very impressed with their promptness they said 9am they were here 9am. Most of all the job looks great !! Thank you AAA Home Construction, Inc. I will definitely call them to do my roof !!"
Response time3 hrs
Response rate97%
51 neighbors recently requested a quote
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%
82 neighbors recently requested a quote
Avatar for A+ Reliable Home Improvements
A+ Reliable Home Improvements
4.9(
89
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Repair - For BusinessFlat, Foam or Single Ply Roofing - Repair- For Business

Serving Southold, NY and surrounding areas

Approved

In business since 2015

Free estimates

Emergency services offered

"Finally! A great estimate, by a really nice, professional , follow by a fast, well done repair to my roof. Can you ask for anything else? I m so happy I found Nick ( the owner) and his company . He Cleaned up everything, and guaranteed his work! He even rearranged his schedule to come and give me an estimate , before I had to leave for work. I had an estimate before his, and that person insisted my skylight needed to be replaced and the whole front of the roof needed to be ripped out. Of course he wanted to charge me a fortune. It s hard finding the honest, qualified people to work on your home, but I m glad I did. I ve already had him give me an estimate on replacing my deck and walk. And even that was reasonable. I know this is a review, but take note, this is a company you can trust. Siding, decks, chimneys, roofs etc. Call Nick at A+ Reliable Home Improvements. You won t be sorry."
Roofing and Chimney
Roofing and Chimney
Roofing and Chimney
Roofing and Chimney
Roofing and Chimney

+5

Response time2 hrs
Response rate100%
14 neighbors recently requested a quote
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Roofing questions, answered by experts

Fall is generally considered the best time of year for roof repairs. The weather is temperate and typically drier, which makes for safer working conditions and fewer delays. The days are also still long enough to complete the work.

Spring is another good option and is a popular time for repairs to fix damage from winter storms. However, frequent rainfall can slow down progress. Spring may be a less busy season for roofers than fall.

Summer can also work for roof repairs, but extreme heat can make asphalt shingles too soft and difficult to work with.

The purchase price of 3-tab shingles is less than that of other material varieties, such as architectural shingles. However, 3-tab shingles generally last far fewer years than even the least expensive architectural ones. Other roofing types, such as metal or clay, also cost more than 3-tab shingles. However, if you plan to stay in your home for many years, the long-term cost of any of these options can compete with 3-tabs because of their longevity.

Pea-sized hail can damage a roof if it experiences hailstorms often, as it slowly causes cracks and deterioration to your shingles. Usually, one hailstorm with pea-sized hail won’t damage your roof, but if you see other damage to your car, grill, and other property, it may be worthwhile to get in touch with your insurance company and have a local roofer come out for an inspection.

While you can technically install TPO roofing over an existing roof, it isn't always wise to do so. The more layers of material you add to your roof, the more weight it must support. You may also develop moisture issues by covering your existing roof with TPO. Your local building codes and regulations may actually require you to remove the existing roof before adding TPO, so check with your local municipality.

Unlike wood decks, Trex decking doesn’t warp. That’s one of the key benefits of installing this decking material. Over time, common issues with these decks include hard water stains, mold or mildew growth, and stains from food spills. Thankfully, with proper cleaning, you can get rid of most stains and mold.

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.