4.7 
79 *The Angi rating for Gutter Repair And Replacement companies in Shady Side, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Gutter Repair And Replacement needs.
*The HomeAdvisor rating for Gutter Repair And Replacement companies in Shady Side, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Gutter Repair And Replacement needs.
Last update on September 24, 2026
Serving Shady Side, MD and surrounding areas
Approved
In business since 2022
Free estimates
Credit card accepted
"Kevin did a excellent job on our gutter guards. His service and workmanship were the best."
Serving Shady Side, MD and surrounding areas
Approved (Corporate)
In business since 2005
Free estimates
Warranties offered
"They replaced my old gutters."
+79
Serving Shady Side, 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."
+19
Serving Shady Side, MD and surrounding areas
Approved
In business since 2018
Free estimates
Credit card accepted
"Asked them to bid on other work like roof and tree trimming that they said they did ..only thing they did were my gutters.... They never got back in touch with me. Just 2 brothers, not a real company. Friendly yes, but not willing to go the extra mile. Quick cash and run guys. Additional Update: They did call me back after a few weeks. They said they were busy and that's why they could not call nor send a proposal."
+12
Serving Shady Side, MD and surrounding areas
Approved
Super Service Award Winner
In business since 2005
Free estimates
Emergency services offered
"All Pro Gutters job went well guys were polite professional . Cleaned up when done ."
+12
Serving Shady Side, MD and surrounding areas
Approved
In business since 1965
Free estimates
Credit card accepted
"Did a great job cleaning the gutters. Pouring rain the next day. Gutters worked great."
+1
Serving Shady Side, MD and surrounding areas
Approved
Super Service Award Winner
In business since 2004
Free estimates
Emergency services offered
"Had a great experience with replacing roof, siding and gutters! Team was helpful, professional and quick with the project."
+73
Serving Shady Side, MD and surrounding areas
Approved
In business since 2014
Free estimates
Credit card accepted
"It went extremely well. They arrived on time and replaced the gutters within 3 hours."
+37
Serving Shady Side, MD and surrounding areas
Approved
In business since 1976
Free estimates
Warranties offered
"I liked this outfit the first time I talked with Zach on the phone. They have a professional and highly respectable demeanor and their is no pressure. I got a real sense that Winfield Builders truly appreciated my business and that the company takes pride in their work and their customer service. We completely overhauled our gutter system including replacing all of the old fascia board with PVC. The quality of the materials are stellar, the workmanship was prompt and precise, and the clean up after the job exceeded expectation. This company is built on good values and is itself probably the best value work and craftsmanship for the money out there. They are the real deal. We plan to rehire them for gutter guards here in the near future once we save funds. Thank you Winfield Builders!"
+56
Serving Shady Side, MD and surrounding areas
Approved
In business since 2001
Free estimates
Emergency services offered
Here at HomeMatters, LLC, we believe in the people we work with and work for. We measure our own teams with not only the pride they take in their work and results, but the measure of respect and integrity they have for each other, our clients, and the project at hand. All of our technicians are certified master installers with over 30 years of experience, working hard to make a change to the reputation of the business we're in. We aim towards educating our customers and lending as much advice as we can towards any remodeling project, whether it is a repair or an installation. Allow us to listen to your needs, and to share the vision you have for your home.
+97
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