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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 - InstallSkylight - Repair, Replace or Seal an Existing SkylightSkylight - 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%
17 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%
135 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%
213 neighbors recently requested a quote
VELUX America LLC
4.8(
6
)
Skylight - InstallSkylight - Repair, Replace or Seal an Existing Skylight

Serving Southold, NY and surrounding areas

Approved

In business since 1941

Free estimates

Credit card accepted

"They were able to replace the skylight in less than 2 weeks after the quote. They did a good job and make the finish on the inside look good. A few weeks later, there was a heavy rain and my new skylight is no longer leaking like my old one that was replaced."
Recommended by60%of homeowners
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Showing 1-10 of 150
Skylights FAQs, answered by experts

Yes, skylights can affect a home’s energy efficiency, either positively or negatively. Properly installed, energy-efficient skylights with Low-E coatings, double glazing, and UV-blocking glass can help regulate indoor temperatures and reduce heating and cooling costs. However, poorly insulated or older skylights can contribute to heat loss in winter and excess heat gain in summer, lowering overall energy efficiency.

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.

Whether you need a permit to install a skylight depends on the scope of the project and local regulations. Generally, permits are required if the installation involves altering the structural components of your home, such as moving roof rafters. In some municipalities, a permit might also be necessary if the skylight protrudes above the highest point of your existing roof. However, if no structural changes are made, a permit may not be needed. The cost for a skylight installation permit is typically under $100. A convenient time to add a skylight is during a roof replacement, as your contractor can incorporate the new opening into the design.

When planning out skylights and deciding how big they should be, it's important to look at the dimensions of the interior space. In addition to changing a room aesthetically, skylights influence the illumination and temperature of the space below. The U.S. Department of Energy recommends that a skylight’s size should never be more than 5% of the floor area in rooms with many windows.

Prevent future skylight issues by conducting regular inspections, ensuring gutters are clean to prevent water pooling, applying protective sealants periodically, and trimming overhanging branches that might cause physical damage to 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.