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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

No, a metal roof will not make your house hot. In fact, metal roofs help keep your home cooler by reflecting heat instead of absorbing and transmitting it inside. Metal also has high thermal conductivity, which means it gains and loses heat quickly. While the sun may heat the metal, the roof rapidly transfers that heat back into the air rather than retaining it. This reflective property can lead to energy cost savings of up to 40%, as your cooling system won't need to work as hard to maintain a consistent indoor temperature.

DIY is not recommended due to safety and expertise requirements. Professional installation ensures proper alignment and sealing.

Roof work is dangerous and exacting, and a misstep could lead to even more costly repairs, so we do not recommend DIYing. If you are dead set on giving it a go, practice safety measures. Wear a harness, only work during mild weather, and have a partner to help. Potentially DIY-friendly jobs include patching up small leaks, sealing areas around the chimney, and replacing a few shingles.

This will depend on your existing roof to some degree, but it’s common to raise a roof 4 to 8 feet. The exact amount you can raise is subject to the existing structure. For most homes with average roof slopes—20 to 45 degrees—you can raise the roof around 5 feet.

The number of roof vents necessary for a 2,000-square-foot house depends on several factors. The calculation depends on the net free area within the attic and whether your municipality requires a 1/150 or a 1/300 ratio of venting square feet to attic square feet. If you install vents with a square-foot opening of one, you'll need either 14 or seven exhaust vents and an equal square-foot amount of intake vents.

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.