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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
58 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

"Brian Shenk was very professional and helpful through the process of replacing our roof. When we had questions he called us back in a timely manner. Project timing was on point. The quality of the roof was good.. Very pleased with the new 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 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

"We experience a major leak in our ceiling dining room.  K&R came out an inspected the attic and found a roof air vent that was installed across my entire roof peak had been leaking for years, he explained the necessary steps to fix the issue (replace entire roof and installed solar powered fan to vent the attic). The wood on the roof in the attic was rotting and growing some sort of "organic material". He covered my roof with a tarp. The quote was reasonable given the amt of work that needed to be done. The material arrive in about a week and the next day after the material arrived they started the work. Even though it was cold, they finished the work in one day. They cleaned up all trash from the old roof. I am very happy that my roof is fixed and looks great. I would recommend them to anyone who wants a professional doing their roof repairs or replacement who uses top quality material and workers.

"
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

Regular cleaning, checking for leaks, and ensuring that downspouts direct water away from the foundation help prolong gutter life.

In most cases, it makes more sense to repair leaking or damaged gutters than it will to replace them. You’ll spend an average of $400 to repair your gutters, while full replacement will cost around $2,000 or more, depending on the gutter material and style and the size of your home. If your gutters are nearing the end of their lifespan—usually around 20 years for aluminum or vinyl gutters or up to 50 years for copper or steel—then it might make sense to replace them, as it could cost you less in the long run.

On average, gutters need to be replaced every 20 years. Unprotected gutters in more extreme weather conditions are more prone to breaking and may need to be replaced sooner. Meanwhile, proper maintenance can extend your gutter’s life span even further. That said, proper installation, gutter hangers to provide additional support, and gutter guards or helmets all play an important role in how long your gutters last.

No—gutters should be designed and properly installed so they are ready to handle any level of rainflow from your roof. If you notice pooling water around your gutters or on the roof, it’s imperative that you contact a gutter repair pro near you—the slope of your gutters could be off and need adjusting.

Yes, professionals can repair or replace sections with seamless copper for better durability.

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.