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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

Top-Rated Roofers in Southold - Updated Nov 2026

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

"Bill Taylor, the President of the company, carefully surveyed the condition of the roof. His detailed, clear estimate addressed all of my concerns. The crew assigned to the project was efficient and courteous. The company is GAF certified, ensuring the warranty will be honored. I highly recommend Four Seasons Roofing."
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

"I consider the roof of a property so essentially important, I went with Express Way Roofing . They did a great timely install. Wonderful craftsmanship and materials.No roof is without leaks, but Express Way Roofing are only a call away. They are prompt and fix the leak asap. I appreciate it and my tenants appreciate it."
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

"Kadri and his team were exceptional! My house, built in the 50s, had a roof leak in a section of the roof that was flat. The roof had been replaced about 15 years ago. ABC recommended changing the shingles with a peel & stick rubber roof for the flatter part of our roof. They explained why, with pictures of my and other roofs. They told us that the underlying plywood was in good shape and didn't need to be replaced, but explained why we had a leak. They didn't try to upsell me, just genuinely told me what needed to be done, and did it in a way that built trust. Why 5 stars?: First, their estimate came in lower than another company I also sourced from Angi. Secondly, they were very responsive to my messages. Third, they scheduled their work around my availability and showed up early and finished on time. Finally, they did high-quality, timely, and thorough work. I'd rehire them in a minute. In fact, we are considering having them fix siding and install leaf filters for our gutters."
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

"We have been having a problem with pigeons hanging around all day on/under our solar panels. I originally had a handyman who was going to install mesh around the edges of the panels and yesterday (the day he was supposed to come) found out he didn't have insurance/license so I canceled. I then went into a Zoom meeting and heard the darn pigeons cooing and fluttering all over the roof and got so upset. I came to Angi and found Best Choice Roofing (aka Best Way) - he called me back right away and in less than an hour he was here. The first thing he did was hand me his business card with his License # on it. Very professional. He got up on the roof, then in a few minutes came down and gave me an estimate. Once I accepted, he called his team to assist and he started on the roof. They were super clean - blew out my gutters, blew everything out from under the solar panels, and made sure to blow the porch and front of my house to remove any debris. I had peace of mind that they were licensed and insured. Today I am happy to announce, I have not heard ONE PIGEON! I know this company usually does more like roofing and gutter-type projects, but I will be letting any of my neighbors with solar panels/pigeons know who to call. Great crew. Thanks so much!"
Response time5 hrs
Response rate95%
96 neighbors recently requested a quote
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Roofing FAQs, answered by experts

In most cases, below 40 degrees Fahrenheit is too cold to replace a roof. The cold affects the shingles, making it more difficult to adhere them to your roof. It also becomes dangerous for contractors to get up on your roof in the cold weather, as there can be ice and slush causing surfaces to become slippery.

Yes, thatched roofs are legal in most areas in the U.S., but you should always check your local building codes to ensure there are no restrictions in your particular area before installing one. Even where they are legal, you’ll usually need to apply fireproofing to the roof to keep it up to code. Keep in mind that a new roof might not increase home value as much if you choose a thatched roof, as they aren’t common in the U.S. and might not be as desirable to many home buyers.

Gable roof construction can last for 100 years or more without needing structural repairs, although the lifespan depends on your climate. Since gable roofs are great at shedding rain and snow, the actual roofing material on top will last for between 20 and 100 years or more, depending on the material you choose. If you’re unsure that your gable roof is up to par, have a roof inspector take a look.

Verify that your roof is licensed and insured by visiting your state's contractor's licensing association. Most states have a database to double-check your contractor's name and address against the information provided. The contractor should also display both their license and insurance on their website with links to the related agencies.

Flat roofs are a solid option for people who want extra outdoor space. Flat roofs are very common in other parts of the world and only recently has the U.S. started to see the benefit in the increased space. Flat roofs are also easier to maintain and pose much less of a safety risk, which allows for more DIY work for handy homeowners. Some people also build green or living roofs that grow plant life. 

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.