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Best gutter repair and replacement pros near Leonardtown, MD

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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

"I had gutter helmet installed 20 years ago and it has been a lifesaver - no gutter cleaning! My house backs up to woods, so lots of tall trees, leaves and pollen. With gutters at 2 and 3 stories, cleaning was necessary, but expensive before Gutter Helmet installation. Today, I had a section of helmet repaired due to damage from a fallen limb. The repair crew was great. They made the necessary repairs and cleaned and checked the gutters on the rest of the house. Gutter Helmet works great and in the event of problems the company is very responsive."
Gutter Helmet
Gutter Helmet
Gutter Helmet
Gutter Helmet
Gutter Helmet

+19

Response time10 hrs
63 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

"Cleaned gutters on two story colonial and also gutters on addition and two car garage.  Several gutters were badly in need of cleaning/unclogging.  Also, Vince adjusted several downspouts, added support brackets, and repaired a few supports on gutters.  We are very pleased with the work."
Recommended by94%of homeowners
Avatar for William Mackay Roofing
William Mackay Roofing
4.8(
106
)
Copper Gutters - RepairGalvanized Gutters - RepairGutter Covers and Accessories - Install or Replace+5 more

Serving Leonardtown, MD and surrounding areas

In business since 1980

Free estimates

Credit card accepted

"Great work! Ben supplied pictures of the work in progress and explained everything that was being done which showed the roof being pulled back to the "studs" and then how they put the new roof on. They also replaced the skylight at no additional cost. I will definitely recommend them in the future!"
Before
During
After
Before
Rubber Patch

+17

Recommended by98%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

Gutters should not drip at the seams. This problem could indicate that water is collecting in the gutters instead of moving to the downspouts. You could have leaves or other debris blocking the flow of water at the seams. Try cleaning the gutters, adjusting the slope, and sealing any holes or cracks in the material to fix this problem.

Poor gutter drainage can cause sagging gutters, roof damage, mold, mildew, rot, basement flooding, and foundation cracks. With gutter replacement costs possible for just $500, getting the right system can save you thousands in repairs down the road.

Most repairs take 2-4 hours, but extensive repairs or full section replacements may take an entire day.

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. 

The most common problem with gutters is clogging from debris like leaves, blossoms, and seeds from surrounding trees. This debris can block downspouts, leading to improper drainage and water overflow.

Other common issues include:

  • Leaks and holes, which can often be repaired with gutter sealant or caulk.

  • Rust, sagging, or detachment from the roofline.

  • Damage from strong storms.

  • Improperly pitched gutters that don't drain correctly.

Regular cleaning in the spring and fall is the best way to prevent most of these problems. You may need to clean them more often during periods of heavy leaf fall.

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.