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Best gutter repair and replacement pros near Callicoon, NY

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Top-Rated Gutter repair and replacement pros in Callicoon - Updated Nov 2026

Avatar for The Brothers That Just Do Gutters
The Brothers That Just Do Gutters
4.5(
291
)
Gutter Covers and Accessories - Install or ReplaceSeamless Metal Gutters - InstallCopper Gutters - Repair+5 more

Serving Callicoon, NY and surrounding areas

Approved

In business since 1999

Free estimates

Warranties offered

"Brothers replaced a damaged gutter over my garage. The work crew arried on time and completed the replacement in a short time. Both the work crew and customer service were professional and courtious. The project was reasonably priced. If you are in need of gutter repair or replacement, I would highly recommend Brothers and their gutters. I may hire them to clean my gutters in the fall."
Rhino Gutter Guard
Seamless Gutters
Heated Gutter
Response time2 days
Response rate100%
8 neighbors recently requested a quote
Avatar for All Day Construction, Inc.
All Day Construction, Inc.
4.9(
105
)
Gutter Covers and Accessories - Install or ReplaceSeamless Metal Gutters - InstallSeamless Metal Gutters - Repair+4 more

Serving Callicoon, NY and surrounding areas

Approved

In business since 2019

Free estimates

Small jobs welcome

"Chris was a pleasure to work with. He arrived on time ready to go. He explained in detail what was needed, what he will do, and provided a cost for the work. He replaced several sections of gutter, made repairs to others and gave them a cleaning. The true test came that evening when it rained overnight and there were no drips or spill overs. A job well done. Will definitely hire Chris again!!"
Plumbing
Plumbing
Outside Home Improvement
Power-washing
power-washing

+4

Response time12 hrs
Response rate91%
8 neighbors recently requested a quote
Seamless Gutter & Supply Co./KC Construction
3.8(
484
)
Seamless Metal Gutters - InstallGutter Covers and Accessories - Install or ReplaceSeamless Metal Gutters - Repair

Serving Callicoon, NY and surrounding areas

Approved

In business since 1985

Free estimates

Warranties offered

"On time for quote visit and the work itself. Left my property neat and clean. No real rain yet to see how the gutters perform but they look great."
Seamless Gutters
Response time1 day
580 neighbors recently requested a quote
Recommended by92%of homeowners
Avatar for Smooth As Silk
Smooth As Silk
5.0(
12
)
PVC Gutters - Repair- For Business

Serving Callicoon, NY and surrounding areas

Approved

In business since 2025

Free estimates

Small jobs welcome

"Kevin from Smooth as Silk arrived ahead of time to install our garbage disposal and replace the kitchen faucet. Before starting, he explained how he would complete the work without disturbing the existing electrical installation. Kevin’s pricing was reasonable, and he took the time to explain how my elderly parent can use the disposal safely and efficiently. I appreciate Kevin’s attention to detail, professional care for our appliances and clear communication!"
Water Softener Install
Saltless Softener
Diverter Cartridge
Faucet Hose
Water Softener

+1

Response time4 hrs
Response rate100%
20 neighbors recently requested a quote
Empire Seamless Gutters
4.5(
19
)
Gutter Covers and Accessories - Install or ReplaceSeamless Metal Gutters - InstallCopper Gutters - Repair+1 more

Serving Callicoon, NY and surrounding areas

Approved

In business since 2004

Free estimates

Customers say: Quality work

"I was very happy with the company, from the first contact with their salesperson Alan to contacts with the office and with Matt and his helper that installed the gutters. I noticed that Matt even cleaned the soffits before installing the gutters and I was amazed how much the new gutters improved the look of my house."
Response time4 days
13 neighbors recently requested a quote
Recommended by93%of homeowners
Avatar for Anywhere Anytime Seamless Gutter and Repairs
Anywhere Anytime Seamless Gutter and Repairs
5.0(
5
)
Copper Gutters - RepairGalvanized Gutters - RepairGutter Covers and Accessories - Install or Replace+5 more

Serving Callicoon, NY and surrounding areas

In business since 2012

Free estimates

Emergency services offered

"Anywhere Anytime Seamless Gutters & Repairs were very professional. I would highly recommend this company. Their work was efficient and done in a timely manner. I received an accurate and fair estimation amount and they were able to come out the day of and work on my gutters. You’ll be truly satisfied with this company."
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+43

Recommended by100%of homeowners
Avatar for Luna Siding & Roofing
Luna Siding & Roofing
4.9(
61
)
Copper Gutters - RepairGalvanized Gutters - RepairGutter Covers and Accessories - Install or Replace+5 more

Serving Callicoon, NY and surrounding areas

In business since 2004

Free estimates

Credit card accepted

"The whole job was amazing. Start to finish I could not say better things about this company. We received our estimate with an amazing price for the scope of work that was to be completed. Alexis in the office was great in getting everything organized and answered all of our questions. Customer service was excellent, great communication and follow up. Rolando really really nice guy and for the roof crew, what can I say. WOW!! They were great and started promptly 7am, I have decent size roof, the whole job completed in one day. 2 layer tear off, roof, fascia, soffits, gutters!!!! Amazing !! Plus, their attention to detail and highly very impressed with the clean up afterwards. The guys went around several times while cleaning up, collecting stray nails, raked additional debris out of my lawn and leaf blower for the rest. I definitely recommend LUNA SIDING and ROOFING! If you are looking, look no more this is the crew you need!!"
Additional Photos
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+150

Recommended by100%of homeowners
Castle - The Window People
3.6(
178
)
Copper Gutters - RepairGalvanized Gutters - RepairGutter Covers and Accessories - Install or Replace+5 more

Serving Callicoon, NY and surrounding areas

In business since 1986

Free estimates

Credit card accepted

"Overall - good quality work, organized, stress free process, a bit pricey but within reason. We had at least 4 or 5 companies come give us an estimate for the 10 windows we needed replaced in our home. Castle's price was not the highest, but also not the lowest. We wanted quality without breaking our bank, so we decided to go with them. The lifetime guarantee was also appealing to us. The sales pitch took a while, but he wasn't our first one, so we knew what to expect. Overall, the salesman was polite and respectful to us the whole time he was over. The scheduling / installation / payment process was almost all very stress free and smooth - they showed up when they were supposed to and worked very efficiently and mostly cleaned up after themselves. Their installers are very well trained. All ten windows were supposed to be done in one day. At the speed their installers were working at, it would have happened. However, they told us that 2 of the 10 windows we ordered came the wrong size and they couldn't finish the job that day (they send their people to come measure the windows.... so it was entirely their mistake). Though it was an inconvenience to us - we had to expect them a second day at our house - the correction was seamless and they took full responsibility for the mistake. We did not pay a penny more over this. A few notes - *The salesman said that the installation would be done completely from the outside of the house. That was not the case. Some of it was done from the inside. Some furniture had to be moved, etc... but again, they left minimal mess. *Strangely, as soon as the windows are manufactured and taken to their warehouse, they call you and can be rather pushy about setting an installation date as soon as possible without much warning ahead of time. That happened to us during the first installation. For the last two windows they were much more accommodating about our schedule. *We had an old bay window replaced with a garden window (much cheaper than a bay window) and though the window itself looks wonderful, they put new trim around the window, seems we are responsible for the sealing / painting of the wood trim and surface. The very same day they installed the windows, we were able to set our heater thermostat 1 to 2 degrees lower and still feel just as warm in the house - definitely proves that the windows are energy efficient. We've had the windows a few months now - all is well. Our only complaint is that in my son's room, where the heater and humidifier are on all night, on extremely cold mornings, there is some condensation on the inside of the window.... that's not supposed to be good.... we did not follow up on it with the company yet, but it only happened in his room a few times during the winter."
Recommended by80%of homeowners
Showing 1-10 of 47
Gutter Repair and Replacement FAQs, answered by experts

Most homes will sustain water damage without gutters. When a home doesn't have gutters, water that runs off the roof will splash down to the ground to create foundation damage, rotting trim, rotting fascia, and soil erosion. A broken or compromised gutter system can be just as damaging as having no gutters. That's why it's essential to talk to roofing pros about how to fix gutters pulling away from house as soon as you notice an issue.

If you are experiencing minor issues with your gutters, such as a small leak or cracks in one or two sections, it makes more sense to repair the issue than to replace your entire gutter system. However, you may need to replace your gutters if they’re frequently detaching from your home or if you notice a buildup of mold or mildew in your basement.

The best way to seal gutters is with a combination of waterproof roofing cement and silicone gutter sealant. This powerful duo works to prevent water from escaping through holes and cracks while allowing for breathability. While you can use polyurethane sealants, silicone sealants tend to be more flexible when it comes to climate. Silicone is UV-resistant and bonds well to many surfaces. However, polyurethane sealant bonds better with wood. 

Sagging gutters stress your downspout, so have your gutters fixed before you secure your downspout.

While minimal drippage may not be problematic, gutters that are constantly leaking or overflowing indicate damage or improper installation. A rain chain gutter or other ornamental feature may produce more dripping than usual. Likewise, rain dispersal systems may also cause water to sprinkle to the ground. However, if you notice pools of water or flooding around your property, then it’s a good idea to have your gutter system inspected.

The Callicoon, NY homeowners’ guide to gutter repairs and replacements

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