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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%
93 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 O'Brien Brothers Contracting, Inc.
O'Brien Brothers Contracting, Inc.
4.9(
214
)
Flat, Foam or Single Ply Roofing - RepairInspection - RoofingAsphalt Shingle 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%
17 neighbors recently requested a quote
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%
97 neighbors recently requested a quote
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Roofing FAQs, answered by experts

Yes, roofers can repair and replace roof trusses. In fact, because trusses are such an important part of your roof’s structure, it’s best to have a roofing contractor deal with a damaged truss. If you try to fix the problem without the right skills or knowledge, your roof could sustain further damage or even collapse.

Before hiring a roofing contractor, it's wise to ask several key questions. Inquire if they are licensed for roof replacement and repair and if they hold any special certifications. Ask if they will be completing all the work themselves or subcontracting parts of it. It's also important to understand the project timeline, whether they will remove the old roof or place new shingles on top, and how they will handle cleanup after the project is complete. Finally, ask about warranties for both work and materials, what recourse you have if issues like leaks arise, and if they can provide customer references.

Yes, chimney flashing is an important element in the complex system that is your roof. Chimneys (and anything else that goes through your roof) provide a great opportunity for water damage. Good flashing prevents a lot of potential damage. 

Many roofers remove satellite dishes as part of their services, especially during roof repairs or replacements. However, they typically won’t reconnect or reinstall the dish. If you no longer need the dish, roofers can dispose of it, but for reuse, you may need a satellite technician to handle reinstallation.

You should definitely be wary of roofing contractors who offer significantly lower prices than their competitors. Most roofers in the area are all dealing with the same cost of materials, and labor costs are often comparable, too. If they’re significantly cheaper than other companies around, it could be a scam. Read reviews and ask other roofing companies and contractors if they’ve heard of the suspected scamming company.

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.