4.7 
127 *The Angi rating for Gutter Repair And Replacement companies in Highland, 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 Highland, 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 April 10, 2025
Serving Highland, MD and surrounding areas
Approved (Corporate)
In business since 2005
Free estimates
Warranties offered
"Fast response to request for quote. Thorough explanation of repair needed & cost of the job. Prompt & efficient repair of gutters & replacement of gutter guards."
+79
Serving Highland, MD and surrounding areas
Approved
In business since 2007
Free estimates
Emergency services offered
"Very good experience. The contractor was responsive with communications and provided a competitive and fair price. No surprises in doing the work, he replaced a broken skylight and repaired displaced shingles on my detached 3-car garage. Professional in his approach and conduct, provided a quote and competently did what he said he would do. I plan to hire him in the future as projects arise."
+24
Serving Highland, MD and surrounding areas
Approved
In business since 1996
Free estimates
Emergency services offered
"Alex was a pleasure to deal with. He came to give me an estimate the same day I called him. He replaced 2 gaskets, did some repairs and sealing. I would definitely recommend him and would use him again. Janet T"
Serving Highland, 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 Highland, 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 Highland, MD and surrounding areas
Approved
Super Service Award Winner
In business since 2005
Free estimates
Emergency services offered
"Our worker, Paul, arrived mid afternoon. He worked through a short downpour and continued into the early evening in the dark! He replaced the gutters, covers and downspouts on the entire house! It looks amazing!"
+12
Serving Highland, MD and surrounding areas
Approved
In business since 1998
Free estimates
Emergency services offered
"Had a section of gutter come loose, was in danger of it pulling off completely, and taking all the soffit with it. Ed came out within a couple hours, took a look, secured the gutter, and came back later that day to complete the repairs. Would absolutely use this company again, and will recommend to others."
+26
Serving Highland, 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 Highland, MD and surrounding areas
Approved
In business since 1995
Free estimates
Warranties offered
"I hired them because of the quality of the supplies and the price. They cleaned up nicely and returned the next day to install the planned gutter replacement. The only item is some damage caused in my fairly new master bath shower. Somehow part of the wall pulled away causing a large gap at the ceiling and cracked grout along the sides. At the very least grout will need to be repaired. Working with Jeff Leach to see what can be done. The contract states that vibration damage is not the company's responsibility."
+2
Serving Highland, MD and surrounding areas
Approved
In business since 1965
Free estimates
Credit card accepted
"Quick to schedule and finish the job (gutter cleaning), though their estimate to repair/replace sections was pricey."
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