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Best siding pros near Southold, NY

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  • Average homeowner rating star icon4.5
    Average homeowner rating
  • Verified reviews icon37
    Verified siding services reviews

Top-Rated Siding pros in Southold - Updated Nov 2026

Avatar for Skyline Roofing and Siding
Skyline Roofing and Siding
4.9(
48
)
Vinyl Siding - Repair or Partially Replace

Serving Southold, NY and surrounding areas

Approved

In business since 2021

Free estimates

Emergency services offered

"Tom from Skyline Roofing and Siding was prompt, friendly and professional. He was able to quickly replace my damaged siding and also went above and beyond by also addressing another issue which a j-channel damaged during the winder. I would highly recommend him for Siding repair/replacement."
Response time3 hrs
Response rate96%
6 neighbors recently requested a quote
Avatar for Undaunted Restoration, Inc.
Undaunted Restoration, Inc.
4.9(
127
)
Asbestos Siding - Repair

Serving Southold, NY and surrounding areas

Approved

Super Service Award Winner

In business since 2005

Free estimates

Emergency services offered

"Undaunted removed asbestos siding and contracted to install new siding thereafter. The entire process took a week. The crews were unfailingly professional and attentive, offering to install a light fixture and repair a porch post free of charge. Excellent company."
Response time1 day
Response rate90%
68 neighbors recently requested a quote
Avatar for Premium Roofing & Siding, Inc.
Premium Roofing & Siding, Inc.
4.4(
191
)
Vinyl Siding - Repair or Partially ReplaceWood or Fiber-Cement Siding - Repair or Partially Replace

Serving Southold, NY and surrounding areas

Approved

In business since 2014

Free estimates

Emergency services offered

"Premium Roofing and Siding came out to give me an estimate on some siding that had blown off. Phil was very prompt and returned my call. That's rare these days. He gave me a fair price and fixed my problem on the spot. He also checked the all the siding and repaired what needed it. It's unusual these days to find a responsible and fair company that doesn't try to rip you off! I highly recommend Premium Roofing and Siding."
chimney LEAD flashing
chimney flashing
repair
repair
repair

+106

Response time9 hrs
1 neighbors recently requested a quote
Recommended by98%of homeowners
Avatar for Four Seasons Roofing
Four Seasons Roofing
4.6(
150
)
Metal Siding: Install or Completely ReplaceVinyl Siding - Install or Completely ReplaceMetal Siding: Repair or Partially Replace+4 more

Serving Southold, NY and surrounding areas

Approved

In business since 1983

Free estimates

Emergency services offered

"Loved working with this company. Very happy with the quality of their work and professionalism-- from the girls in the office to the crew they sent to replace my parent's roof, the entire job was seamless. They were prompt, courteous, cleaned up our yard meticulously which is really great. Even though we had this done a few years ago, had to write a review because the roof came out great and still looks brand new. I would recommend them highly. Just as a side note, these guys have been in business for over 3 decades and have won so many awards... not everyone is GAF certified with Master Elite status, but they are. Check them out, we're very fussy and do our homework before we hire someone for something as important as a roof, and so glad we chose them to do the work. Job well done!"
GAF Preferred Contractor Badge
Additional Photos
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+19

Response time2 days
Response rate100%
14 neighbors recently requested a quote
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Siding FAQs, answered by experts

Some homeowners use caulk on the edges of clapboard siding to help seal it. However, this method invites new problems. With so many gaps sealed, clapboard siding is often unable to drain properly and moisture from rain or other sources can build up inside. This can lead to rot and other issues over time. When repairing clapboards, it’s best to avoid caulking the final product. The exception is trim around windows and doors, which should be caulked to avoid moisture problems.

Yes, vertical and horizontal siding both come in the same materials, including wood, vinyl, aluminum, and engineered wood. The material you choose can significantly affect your siding’s overall price, lifespan, insulation properties, and maintenance costs. 

Similar to other types of wood siding consisting of natural materials, cedar siding should last 20 to 40 years. However, the lifespan for any wood siding, including cedar, can be far shorter without the proper repair and maintenance work. Don’t put off making repairs, or problems could worsen quickly. While you can repair minor holes and cracks in the siding shakes, rot and warping requires replacing the boards. 

DIY is possible, but professional installation ensures weatherproofing, insulation, and proper fastening.

Yes, by sourcing materials and textures that blend seamlessly.

The Southold, NY homeowners’ guide to siding services

From average costs to expert advice, get all the answers you need to get your job done.