Top-rated gutter repair and replacement pros.

Best gutter repair and replacement pros near Leonardtown, MD

Enter your zip and get matched with up to 5 pros

Need a pro for your gutter repair and replacement project in Leonardtown, MD?

Select your specific project to find the pro for you.

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
56 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 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

"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
...
Showing 1-10 of 81
Gutter Repair and Replacement FAQs, answered by experts

Any small amount of standing water can be damaging to your gutters. It’s recommended that a ¼ inch puddle or more should be addressed. Failure to keep water from pooling in your gutters can result in clogs, algae growth, and pests that damage your gutters over time. 

Yes, caulking or sealing your vinyl gutters is a good way to help prevent gutter leaks. When you’re installing gutters, it’s important to overlap the sections to help avoid issues like leaks or drips, but they can still happen. In this case, adding caulk can help. Make sure to use a caulk designed for multiple surfaces, like a silicone-based caulk. You can also purchase a gutter sealant as well, which is specifically designed for this purpose.

The average cost to install or replace gutters is around $2,000, with typical project costs ranging from $900 to $7,000. Most companies charge between $4 and $30 per linear foot. The total price depends on several factors, including the size of your home, the complexity of its footprint, the gutter material (e.g., vinyl, metal), and the gutter style (e.g., half-round, custom-built). Additional elements like downspouts, corners, and optional add-ons like gutter guards can also increase the price. The condition of your roof is another consideration, as new gutters cannot be installed on a rotting or sloping roof. While it can be an expensive upfront cost, new gutters are a worthwhile, long-lasting investment for protecting your home's exterior. You can save up to half on labor costs by installing them yourself.

Yes, gutter repair is almost always worth the investment. Some homeowners believe that gutter repairs are only to improve the home’s curb appeal, but gutters play a pivotal role in protecting your foundation from damage and structural instability, and they also prevent water damage to your soffits, fascia, roof, and exterior walls. You will pay an average of around $400 to have your gutters professionally repaired, but it’s worth it even for the peace of mind of knowing that one of your largest investments is adequately protected from the elements.

Absolutely—and lots of it. Overflowing water from your gutters can damage your siding and your roof. All of the moisture getting into the cracks and crevices of your home can lead to mold or mildew problems down the line. In addition, when water pools around your home, it needs a place to go—and sometimes it ends up inside the house, creating a very unwanted flood.

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.