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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

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.

In most cases, installing skylights will add value to your home, making them a worthwhile investment for many homeowners. Buyers are often attracted to the aesthetic appeal of skylights, as they make rooms feel brighter, airier, and more spacious by introducing natural light without compromising privacy. Beyond aesthetics, skylights can offer monetary benefits by potentially reducing energy bills. Additionally, models that can be opened provide extra ventilation, which is particularly useful in hotter climates for allowing accumulated hot air to escape from the ceiling. However, the return on investment depends on several factors. To maximize value, it's crucial that the skylights are installed by an experienced professional to avoid risks like water damage, which can deter savvy buyers. Regular maintenance and cleaning are also important. Furthermore, choosing the right frame and glazing materials for your specific climate will enhance their performance and appeal. While skylights are generally seen as an asset, homeowners should also consider the initial cost, which averages around $1,500 for installation.

Professionals repair or seal a skylight by inspecting for damages, resealing any gaps with appropriate weatherproofing materials, replacing cracked glass or seals, and ensuring the frame is tightly fitted to prevent future leaks and ensure proper drainage.

This is based on personal preference, budget, and the vibe you are going for with your holiday lighting. If you are looking for the cheapest option, incandescent lights are a budget-friendly choice. You can also opt for sheets of lights that cover areas such as trees and bushes for easier installation.

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.