4.6 
281 *The Angi rating for Gutter Repair And Replacement companies in Annapolis, 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 Annapolis, 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 Annapolis, 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 Annapolis, MD and surrounding areas
Approved (Corporate)
In business since 2005
Free estimates
Credit card accepted
"Replacement of old gutters with Leaffilter's gutter. The pricing was reasonable, the work was scheduled and performed in due time, and I believe we got a good service at a good price."
Serving Annapolis, 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 Annapolis, MD and surrounding areas
Approved
In business since 2018
Free estimates
Credit card accepted
"Mr. Canales and his team were professional and conscientious. They did a very good job with both roof repair and drywall patching and painting."
+12
Serving Annapolis, 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 Annapolis, 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 Annapolis, 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 Annapolis, MD and surrounding areas
Approved
Super Service Award Winner
In business since 2004
Free estimates
Emergency services offered
"I thought getting my gutters replaced was going to be a big hassle. But working with Home Genuis it was a breeze. From Eric and Anthony to Tony and Angel everyone was knowledgeable and nice, no pressure. Would highly recommend them."
+73
Serving Annapolis, 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 Annapolis, MD and surrounding areas
Approved
In business since 1965
Free estimates
Credit card accepted
"The arrived very soon after requesting their service. They completed the work and explained problems that were found. They came back the next day to complete my gutter replacement the next day after I agreed. Very professional and clean after service."
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