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Best skylight pros near Southold, NY

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Top-Rated Skylight pros in Southold - Updated Nov 2026

Avatar for O'Brien Brothers Contracting, Inc.
O'Brien Brothers Contracting, Inc.
4.9(
214
)
Skylight - Repair, Replace or Seal an Existing SkylightSkylight - InstallSkylight - Install - For Business+1 more

Serving Southold, NY and surrounding areas

Approved

Super Service Award Winner

In business since 2015

Free estimates

Emergency services offered

"Dealing with O'Brien Brother's Construction was a absolute pleasure from start to finish. The job consisted of removing and replacing a 30x30 vented skylight, new water & ice shield installed along with matching the existing shingles. The job came out great. I highly recommend this company for your next job."
Copper flashings
Plywood
G.A.F Architectural shingles
Only the best materials
Chimney flashing and roof repairs

+53

Response time9 hrs
Response rate94%
31 neighbors recently requested a quote
Avatar for Landstar Construction
Landstar Construction
5.0(
28
)
Skylight - Repair, Replace or Seal an Existing SkylightSkylight - Install

Serving Southold, NY and surrounding areas

Approved

Super Service Award Winner

In business since 2015

Free estimates

Emergency services offered

"Hired land star to fix a leak in my kitchen coming from ice buildup on my roof. Steve came the next day. New exactly what was wrong with roof and gave a fair price. Came the following day removing snow and ice. Then came the next day and fixed roof. He was prompt and is very knowledgeable. Would definitely recommend and use him again."
COPPER FLASHING
NEW ROOF
SKYLIGHT REPLACEMENT
SKYLIGHT REPLACEMENT
Paint Gaco

+3

Response time4 hrs
Response rate100%
134 neighbors recently requested a quote
Avatar for Lifetime Quality Construction Inc
Lifetime Quality Construction Inc
4.9(
117
)
Skylight - Repair, Replace or Seal an Existing Skylight

Serving Southold, NY and surrounding areas

Approved

Super Service Award Winner

In business since 2025

Free estimates

Emergency services offered

"I recently had a skylight repaired and a small new roof installed, and I'm very satisfied with the work. The team was professional, punctual, and respectful of the property throughout the project. The skylight no longer leaks and looks great, and the new roof section blends in perfectly with the existing structure. They explained everything clearly before starting, provided a fair quote, and completed the job on time. Clean-up was thorough, and I appreciated their attention to detail. I’d definitely recommend them for both small roofing jobs and more specialized repairs like skylights"
Roofing siding chimney
Roofing siding chimney
Roofing siding chimney
Roofing siding chimney
Roofing siding chimney

+150

Response time4 hrs
Response rate100%
227 neighbors recently requested a quote
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Showing 1-10 of 150
Skylights FAQs, answered by experts

To maintain a skylight and ensure its performance over time, regular maintenance is required. This includes periodically cleaning the glass and frame to remove dirt, debris, and condensation. It is also crucial to inspect the seals and flashing at least once a year for any signs of wear, degradation, or leaks, paying special attention after heavy storms. Ensure that the drainage system is clear to prevent water buildup and potential leaks. Address minor issues like cracks promptly and consider occasional resealing to prevent drafts and moisture problems. While energy-efficient skylights with Low-E coatings or double glazing may require less upkeep, periodic professional servicing can help keep any skylight in optimal condition.

Yes, you can replace a skylight without changing the entire roof—if the roof is in good shape. First, you need to make sure the roof around the skylight is intact and free of damage. Quality installation is crucial to prevent leaks, including replacing the flashing, which seals the skylight to the roof. While replacing the skylight alone is doable, it can make sense to replace both at once to streamline the work, coordinate the warranties, and reduce the risk of future leaks. If you’re unsure, reach out to a professional for help in deciding the best approach.

Skylights might sometimes increase your homeowners insurance premium, but the increase is usually minimal. Some home insurance companies won’t adjust your premium with the addition of a skylight, so you can contact your insurer or your professional skylight installer to ask about any expected changes. It’s crucial to have an expert install the skylight, as insurance companies may not insure your roof or cover water damage that results from a non-professional skylight installation.

Most homeowners insurance policies cover skyight damage that is caused by hail. Hail damage is considered a covered peril under most standard insurance policies. However, this only applies if your skylights were properly installed. Also, insurance policies vary, so be sure to check your individual policy to see if skylight hail damage is covered.

Yes, you can install skylights on an existing roof, and it’s a common service that many homeowners opt for, especially on older homes built when skylights weren’t as prevalent. The installation process will be a bit more involved, and the design and planning process will take longer, meaning you’ll pay more to install a skylight on an existing roof than you would in new construction. The process involves cutting a hole in the roof, moving rafters, if necessary, and installing and sealing around the skylight.

The Southold, NY homeowners’ guide to skylight services

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