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TRUSTED BY CHESTER, MD HOMEOWNERS

  • Average homeowner rating star icon4.7
    Average homeowner rating
  • Verified reviews icon132
    Verified gutter repairs and replacements reviews

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

Avatar for Universal Windows Direct of Baltimore
Universal Windows Direct of Baltimore
4.1(
62
)
Gutter Covers and Accessories - Install or ReplaceSeamless Metal Gutters - Install

Serving Chester, MD and surrounding areas

Approved

In business since 2002

Free estimates

Warranties offered

Universal Windows Direct was founded in April of 2002 by William Barr and Michael Strmac. It was their mission to create a home improvement company that offers high quality home improvement goods at the best possible value. What began as two guys in a 350 square foot office quickly grew to become one of the nation's leading remodeling companies. Today, Universal Windows Direct represents thousands of customers and has a rapidly growing network of locations nationwide, all of which are actively involved in the communities they serve.

Double Hung Window
Double Hung Window
Double Hung Window
Double Hung Window
Recommended by80%of homeowners
Avatar for All Pro Exteriors
All Pro Exteriors
4.6(
62
)
Copper Gutters - RepairGalvanized Gutters - RepairGutter Covers and Accessories - Install or Replace+5 more

Serving Chester, MD and surrounding areas

In business since 1991

Emergency services offered

"Vince called me back within hours of my sending him a message through Angie's List.  Even though he does not list Montgomery County as one of his service areas, he was completely willing to help us out.  In my message, I had requested the work to be done onsite but Vince explained why having him pick up the generator and take it back to his shop to work on it would make more sense.  His charge for pick-up and delivery back to us was only $34.95.
When Vince came to pick up the generator, he was on time and was able to give me a ballpark cost for the work (which turned out to be very accurate).  He said that he could get it back to us in 3-4 days but I asked if he could do it faster as there was a snow storm predicted for the next day or so.  Vince agreed to a shorter time line and ultimately got the generator back to us within 1 day!  There ended up being no snow storm but we got our generator back in working condition - along with a booklet of care instructions, a copy of our invoice, and a service history form.  A few days later we received a hand-written Thank You card in appreciation of our business.  I can't imagine how the service could have been any better.  We will use Vince for any future small engine repairs/maintenance we have and highly recommend him and his services.
"
Recommended by94%of homeowners
Avatar for Gutter Cleaning Pros
Gutter Cleaning Pros
4.6(
25
)
Copper Gutters - RepairGalvanized Gutters - RepairGutter Covers and Accessories - Install or Replace+5 more

Serving Chester, MD and surrounding areas

In business since 2016

Free estimates

Emergency services offered

"I called Gutter cleaning Pros and set up an appointment for a free estimate to have my gutters cleaned. He came out on time and was very professional! After I agreed, He got right to work cleaning the gutters and flushing the downspouts. He even provided an inspection report and pics of other things he saw needed to be done! He did a fabulous job and I can't wait to have him back!"
Gutter Cleaning
Gutter Cleaning
Gutter Cleaning
Additional Photos
Additional Photos

+1

Recommended by95%of homeowners
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Gutter Repair and Replacement FAQs, answered by experts

Once you’ve installed your gutters, you'll need to maintain them. You should clean your gutters once or twice a year to keep them functioning correctly. But if climbing a ladder and scooping out handfuls of wet leaf gunk is just not your thing, you can hire a professional gutter cleaner near you to do the job. 

If you’re replacing your roof, you don’t need to worry about replacing your gutters as long as they’re functional and in good condition. Some roofers may recommend temporarily removing gutters to prevent them from damage during a roof replacement, but the right professional can reduce this risk. Replacing your gutters would only be necessary if your gutters are in bad shape and already need replacing.

With routine maintenance, gutters don’t usually need to be replaced for 20 years, but there are warning signs that they might need early replacement. Signs that your gutters need to be replaced include sagging, visible cracks or holes, peeling paint, rust, standing water in your gutter, and water leaking into your basement. Pushing off replacing your gutters can lead to extensive damage to both the interior and exterior of your home. Regular maintenance can help your gutters last all 20 years — and sometimes, even longer. 

Water should not be dripping behind your gutters. Rain dripping between your gutters and the fascia might indicate that the gutters are misaligned with the fascia board or there are loose screws in the gutters, allowing water to pass through. Start by checking for these issues and make repairs ASAP.

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

The Chester, MD homeowners’ guide to gutter repairs and replacements

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