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 04, 2026
Serving Annapolis, MD and surrounding areas
Approved
In business since 2022
Free estimates
Credit card accepted
"VERY PROMPT AND BEAUTIFUL INSTALLATION OF NEW GUTTERS, AT A VERY REASONABLE PRICE."
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
In business since 1996
Free estimates
Emergency services offered
"It is a work in progress; still need to see how well the repairs hold up under heavy rainfall and wind. Then I will be able to finalize my assessment of the work done."
Serving Annapolis, 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 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
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 Annapolis, 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 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."
Serving Annapolis, MD and surrounding areas
Approved
In business since 1993
Free estimates
Customers say: Quick response
"Peter Holden and his crew were terrific. They not only installed the gutters and downspouts on my two story house and the detached garage, but repaired and painted the fascia board and other trim that had been damaged over the past couple of years while the roof and gutters were leaking. The gutters are wider and covered - a big improvement over the old gutters - and they have a lifetime guarantee. The house and garage took three days, and each day they completely cleaned up. I plan on hiring them again for some major work on the outside porches."
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