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TRUSTED BY LEONARDTOWN, MD HOMEOWNERS

  • Average homeowner rating star icon4.7
    Average homeowner rating
  • Verified reviews icon21
    Verified gutter repairs and replacements reviews

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

Avatar for Gutter Helmet
Gutter Helmet
4.6(
62
)
Gutter Covers and Accessories - Install or Replace

Serving Leonardtown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 1981

Free estimates

Warranties offered

"This is an excellent company and the product really works. I used to have to worry about constantly keeping my gutters free of leaves. Gutter Helmet screens keep the leaves out. The company is very responsive whenever I need maintenance. I highly recommend them."
Gutter Helmet
Gutter Helmet
Gutter Helmet
Gutter Helmet
Gutter Helmet

+19

Response time10 hrs
62 neighbors recently requested a quote
Recommended by58%of homeowners
Avatar for Priceless Home Improvements, LLC
Priceless Home Improvements, LLC
4.6(
38
)
Gutter Covers and Accessories - Install or ReplaceSeamless Metal Gutters - Install

Serving Leonardtown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 2011

Free estimates

Emergency services offered

"Sam stopped by my house one day and mentioned that there was an issue with my roof and that Priceless Home Improvement would help be with the entire process to replace it at no cost to me. At this time, I had so many other obligations going on that did not have the time or energy to take on another thing. He was so persusaive that I went ahead that signed up to have the roof replaced. Priceless took it from there. They handled everything from meeting the inspector from the insurance company to the final replacement of the roof. the work was outstanding and this whole process was painless with Priceless Home Improvement. I would recommend Sam and Priceless Home Improvement to anyone interested in going with a reliable company to replace their roof."
Deck
Deck
Deck
Deck
Deck

+21

Response time3 days
2 neighbors recently requested a quote
Recommended by50%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 Leonardtown, MD and surrounding areas

In business since 1991

Emergency services offered

"We called Vincent on a Sunday morning for an emergency cleaning since we were leaving for vacation Monday evening. We had a huge flood from the ac unit in our attic and we thought it was due to the gutters being clogged, not allowing the water the properly drain.  When I called he informed me he was located approx. 2 hrs from my home so I immediately thought there was no way he would come out on a Sunday to clean gutters.  However, he called back and offered to send someone if we couldn't find another company.  We agreed to a time and Jamie showed up at 2:00 and immediately went to work.  He also went in the attic to check the issue.  Although, the gutters were not the issue the service and response time was fantastic.  I would highly recommend using them."
Recommended by94%of homeowners
Avatar for Supreme Window and Door
Supreme Window and Door
4.8(
69
)
Copper Gutters - RepairGalvanized Gutters - RepairGutter Covers and Accessories - Install or Replace+5 more

Serving Leonardtown, MD and surrounding areas

In business since 2005

Free estimates

Emergency services offered

"

Scheduled an appointment with Albert Hoffman, Senior Product Specialist, to come out and give me an estimate to replace 15 windows and a sliding glass door.  He's great...was punctual and very professional!!  The estimate he gave was by far the best I had received plus it included adjusting my storm door and wrapping my garage door.  I decided to move forward with Supreme and do the project in stages.  I started with the first floor and replaced the eight windows with energy-efficient triple pane Simonton 5500 windows.  Albert said I would receive a call within a week for someone to come and take measurements and that he would also follow-up with me after the install was completed.  Within that time frame I received a call from John and scheduled him to come and take the measurements.  He indicated it would take approximately 3-5 weeks for the windows.  In a little over three weeks I received a call that the windows were ready to be installed.  Due to the frigid cold weather, I scheduled the install for Friday, January 9th.  The crew: John, Bobby, Carlos, and Justin arrived around 8:15 am.  They set up and started removing the windows one at a time.  Carlos and Justin worked outside and John and Bobby worked inside.  They were very professional and cleaned up as they went along replacing each window.  They also wrapped my garage door and Justin adjusted my storm door.  The whole process went extremely well.  I couldn't have asked for a better crew...they were awesome!!  Albert did follow-up with me a few days later to see how everything went.  I am a very happy customer and can already feel the difference with my new windows!!  Highly recommend Albert and Supreme Window & Door!!     

P.S. The remaining seven windows on the second floor and the sliding glass door will be replaced at a later date. 


"
Windows
Bay window capped
Sliding Glass Door
Recommended by95%of homeowners
Avatar for Elite Cleaning Services LLC
Elite Cleaning Services LLC
4.3(
588
)
Copper Gutters - RepairGalvanized Gutters - RepairGutter Covers and Accessories - Install or Replace+5 more

Serving Leonardtown, MD and surrounding areas

In business since 2008

Free estimates

Credit card accepted

"They do a good job but are extremely expensive.  The last cleaners I had charged me $115, Elite charged me $165.  I expected with such a drastic cost increase that the cleaning be OUTSTANDING.  They did a good job, but not worth the cost increase.   Out of the 7 times they cleaned for me they arrived on time 6 out of the 7 times.  The one time they did not show, of course happened to be the day I had guests arriving in the afternoon, and the customer service handling the situation left something to be desired.  I was promised the replacement team would show up in 3 hours, then they were 45 minutes late on top of that, so arrived almost 4 hours after their originally scheduled time.  I'm used to being comped a cleaning or at least offered half off when a mistake like this happens, I was only offered 10% off my cleaning after I specifically asked how i would be compensated for this huge inconvenience, only after expressing intense frustration did the 10% increase to 15%.  I would expect to be compensated so much more following such a large mistake and me having to rearrange my work and my kids schedules to accommodate their tardiness.  They aren't worth the money, I can easily find another service for significantly less money who will do a comparable cleaning.  
"
Additional Photos
Additional Photos
Recommended by82%of homeowners
Avatar for K&R RoofMasters, Inc.
K&R RoofMasters, Inc.
4.9(
84
)
Copper Gutters - RepairGalvanized Gutters - RepairGutter Covers and Accessories - Install or Replace+5 more

Serving Leonardtown, MD and surrounding areas

In business since 2006

Emergency services offered

Credit card accepted

"Robert arrived promptly and was very friendly and professional.  We have alot of LF of gutters and 12/12 pitch roofs and dormers.  He did the work quickly and cleanly, bagging all of the debris.  Normally, when I do it, the ground looks like a hurricane had been through but with K&R, I couldn't even tell the gutters had been cleaned.  Beautiful!
It can be difficult to hire someone for a job you would normally do yourself but, when it's necessary, it's great to find the right place. Thanks!
"
Walkable Roof
Skylight Leaking
Poorly Ventilated Roof
Poorly Ventilated Roof
Poorly Ventilated Roof

+7

Recommended by98%of homeowners
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Gutter Repair and Replacement FAQs, answered by experts

There are a handful of things you can look for to determine if you need to pay for gutter repairs, including the following:

  • Water leaking from the underside of your gutters during rainfall

  • Visible gaps between your gutters and your roof

  • Frequent issues with gutters overflowing or holding standing water

  • Gutters that sag or pull away from the house

  • Water damage to soffits, fascia boards, or other building materials

  • Mold growth on your exterior walls

  • Soil erosion underneath your roof overhang

  • Foundation leaks or inward bowing of foundation walls

Icicles don't necessarily mean your gutters are clogged or bad, but they can indicate an underlying issue. While clogged gutters can cause icicles to form, the problem could also be an ice dam on your roof from poor insulation. In that case, melting snow can refreeze in the gutter even without a clog. Regardless of the cause, the weight of the ice can damage your gutters or even rip them completely off the house. If you are unsure of the underlying problem, it's best to call a roofing company to assess the issue and implement a permanent solution.

The gutter gauge is a measurement of the thickness of the gutter material. If you have gutters that are too thick and heavy for the screws and brackets holding them in place, they may sag. Materials that are too thin could suffer damage that leads to sagging. A professional gutter installer can ensure you have the right gutter gauge.

One of the biggest causes of gutter leaks is clogged gutters. If your gutters are full of debris and leaves, water will back up and eventually overflow outside of the gutter. Other common causes of gutter leaks include loosened gutter fasteners, faulty gutter slopes (sagging gutters), separated joints, and cracks or holes.

If you don't repair your home’s gutter leaks, water or the gutters themselves can damage your home’s siding, roofing, foundation, and landscaping. Untreated leaks encourage mildew, mold, and rot, depending on the type of siding material. The foundation, chimney, window frames, and drywall can also crack over time, leading to costly repairs. 

The Leonardtown, 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.