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TRUSTED BY OLD GREENWICH, CT HOMEOWNERS

  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon355
    Verified roofing services reviews

Top-Rated Roofers in Old Greenwich - Updated Nov 2026

Avatar for MJA Contracting LLC
MJA Contracting LLC
5.0(
32
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For Business+26 more

Serving Old Greenwich, CT and surrounding areas

Approved

In business since 2005

Free estimates

Emergency services offered

"I would highly recommend Manny and his team to anyone in need of roofing services!! Manny was great at communicating about the project and making suggestions. The team arrived on time, worked efficiently and left everything clean. The quality of their work was excellent! Another family member had used Manny in the past and was also extremely happy with their new roof!"
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+96

2 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for Roof Systems Of Connecticut
Roof Systems Of Connecticut
4.6(
340
)
Metal Roofing - Repair - For BusinessNatural Slate Roofing - RepairNatural Slate Roofing - Repair- For Business

Serving Old Greenwich, CT and surrounding areas

Approved

In business since 2002

Free estimates

Emergency services offered

"Roof Systems is amazing ... they are the Superman of roofing. Our home sustained serious roof damage caused by a tropical wind storm. Roof Systems came out the same day to access the damage and then placed protection so our roof would not sustain more damage or create internal damage to our home. Their work is always done with pride and a high standard of perfection. They are always professional and friendly. I will only allow Roof Systems to handle our roofing needs."
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 EPDM ROOF
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+9

Response time5 hrs
Response rate100%
Recommended by95%of homeowners
Avatar for Mighty Dog Roofing of Fairfield County
Mighty Dog Roofing of Fairfield County
5.0(
9
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair+26 more

Serving Old Greenwich, CT and surrounding areas

Approved

In business since 2012

Free estimates

Emergency services offered

"Mighty Dog Roofing have such a high bar! We appreciate the amazing transparency and integrity throughout the whole procedure of our full roof replacement from beginning to end. The end result is a stunning and sturdy metal roof. Big shout out to Tom for making me understand the pros and cons between asphalt shingles and metal roofs. The drone superscan was also very cool!"
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+7

2 neighbors recently requested a quote
Recommended by88%of homeowners
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Roofing FAQs, answered by experts

You shouldn’t put a new roof underlayment over an old one for a few reasons. Old felt must be removed in order to assess the condition of your roof decking, such as rotting wood or other structural issues. Also, if your roofer doesn't install a fresh layer of felt as is required by shingle manufacturers, your warranty may be voided. Finally, old underlayment removal is often included in the cost of roof repair or replacement, so there's no real benefit to leaving it on before installing a new layer.

Sometimes chimney caps blow off during storms or fall off after rusting away. While this typically won’t cause structural damage, failing to replace a chimney cap can. A chimney cap prevents moisture, animals, and debris from entering your chimney, all of which can cause serious problems, such as damage to the masonry or blockages in the flue.

Chimney crowns are located above the final brick layer at the top of a chimney. It’s important to get regular chimney maintenance and inspection, because it is near impossible to spot chimney crown damage without getting on your roof.

Fall is generally considered the best time of year for roof repairs. The weather is temperate and typically drier, which makes for safer working conditions and fewer delays. The days are also still long enough to complete the work.

Spring is another good option and is a popular time for repairs to fix damage from winter storms. However, frequent rainfall can slow down progress. Spring may be a less busy season for roofers than fall.

Summer can also work for roof repairs, but extreme heat can make asphalt shingles too soft and difficult to work with.

When installed and maintained properly, a cedar shake roof should last up to 60 years. Severe weather and high winds will damage your roof, reducing its life span. Expect a shorter life span if the roofer didn't use top-grade material, didn’t have cedar shake expertise, didn’t create the proper ventilation, or didn’t use the correct fasteners. Keeping up with maintenance will help it last longer. It’s also a good idea to get roof inspections on a regular basis to help spot repairs before they become major issues.

The Old Greenwich, CT homeowners’ guide to roofing services

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