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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%
98 neighbors recently requested a quote
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Roofing FAQs, answered by experts

Using an ice and water shield underlayment under a metal roof is a good way to protect the roof and your home from damage in colder climates that see a lot of winter weather. Traditional underlayment isn’t effective underneath a metal roof, though, so be sure to install one specifically made for metal roofs to get the best protection.

The exact weight of a bundle of shingles depends on the shingle type, manufacturer, and other factors. It can weigh anywhere between 45 and 800 pounds.

Yes, many contractors offer warranties for their work. Confirm terms before hiring.

For homeowners who plan to stay in their homes for a long time or never want to have to deal with replacing a roof again, rubber roof shingles are likely worth the added investment amount over asphalt shingle varieties. While the initial cost of installing a rubber shingle roof will be significantly higher, their long life spans can be worth it in the long term. Consider the curb appeal of a rubber roof, though, as other roofing materials, like metal, can look better and offer even greater value.

You can install solar panels on a flat or pitched roof, but keep in mind that they will need to rest at a 30- to 50-degree tilt for optimal sun absorption. It costs more to install solar panels on a flat roof because you will need to install a framing system and likely hire a structural engineer. If your roof has a pitch of more than 40 degrees, it may not be a good candidate for solar panels.

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.