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
"He arrived promptly, cleaned the gutters and made arrangements for a couple of small repairs"
Serving Shady Side, MD and surrounding areas
Approved (Corporate)
In business since 2005
Free estimates
Warranties offered
"Gutter now fully functional. Went out during a recent rain and the gutters worked fully as advertised - better than the original."
+79
Serving Shady Side, MD and surrounding areas
Approved
Super Service Award Winner
In business since 2004
Free estimates
Emergency services offered
"This was a great team that came and replaced our old gutters. Very friendly and great communication throughout the process."
+73
Serving Shady Side, MD and surrounding areas
Approved
Super Service Award Winner
In business since 1981
Free estimates
Warranties offered
"The project replaced LeafFilter gutter covers w/ GutterHelmut. GutterHelmet is far superior to LF. LF clogs so while the gutters are protected, the rainwater spills off of the cover onto the ground below. My high roof has had GH for 20 years, no problem. My low roof had LF for 16 years but no more. The removal/installation went smoothly w/ a friendly, competent crew."
+19
Serving Shady Side, MD and surrounding areas
Approved
In business since 2018
Free estimates
Credit card accepted
"Also had Canales Service do some brick/masonry repairs. Totally professional, efficient, and outstanding results. Highest recommendation!"
+12
Serving Shady Side, MD and surrounding areas
Approved
Super Service Award Winner
In business since 2005
Free estimates
Emergency services offered
"I called for a quote an the next day Mike Suermann came out to look at what I needed. He took great care to give me what needed and thought was best for the house. He was a great wealth of knowledge. Our gutters and guards were installed the next business day. They cleaned up so well you wouldn't have known they were there. I am 100% satisfied with everything."
+12
Serving Shady Side, MD and surrounding areas
Approved
In business since 1976
Free estimates
Warranties offered
"Winfield Enterprises did gutter work (gutter installation) on my home (a 3,000 square foot home). It only took them about 4 hours to complete. The service was top notch, no complaints. The price and materials were far better than other quotes I received from other companies, and the job was done perfectly and within the expected time frame. Five stars for these guys."
+56
Serving Shady Side, MD and surrounding areas
Approved
In business since 2001
Free estimates
Emergency services offered
"Perfect. I scheduled an appointment on the Angi app, and Mike came on time. He thoroughly reviewed the damaged siding on our initial visit. The original siding around our carport had a cap over the top that fell away, and the team came up with a different way to attach the siding so that problem wouldn't happen again. The crew arrived on time on the repair day, completed the task, and reviewed it with me before leaving. They provided excellent communication and service throughout the whole process. I highly recommend them and will be calling on them again for future remodeling needs!"
+97
Serving Shady Side, MD and surrounding areas
Approved
In business since 1965
Free estimates
Credit card accepted
"Did a great job and caught a hole in my gutter"
Serving Shady Side, MD and surrounding areas
Approved
In business since 2001
Free estimates
Customers say: True professional
"I received very professional and courteous service from Mike Shin, who wrote up a highly specific and detailed proposal for a small exterior trim repair job. The repair was done in a timely fashion and exactly as proposed. I was very happy with Home Matters and plan to use their services again. I recommend them."
+37
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