Consistent 5-star reviews — 579 Google ratings average a perfect score
Fast scheduling — same-day and next-day appointments come up repeatedly
What does window, siding, or gutter work cost in Greater Boston?
Typical Greater Boston range for this kind of work, from regional averages — not a quote from Gutter Cowboy LLC. Use it to sanity-check bids, then get the real number in writing.
Windows / Siding / Guttersgutter cleaninggutter repair
On-the-spot repairs — brackets and downspouts fixed during cleanings, often free
Storm response — ice-dam and blizzard damage repaired within days
Verified HIC license — Massachusetts registration is active under Jason Aleman
AI phone booking — a 2025 review flagged the automated voice system before it worked
Gutter Cowboy is built around one job: cleaning, repairing, and installing seamless gutters across Southeastern Massachusetts and Rhode Island. The company says it has covered the Lakeville-Middleborough-Bridgewater corridor and towns as far as Plymouth and Wareham since 2017. Jason Aleman runs it, and the reviews that keep piling up — 579 of them on Google, every one five stars — tell a remarkably consistent story: he shows up when he says he will, texts updates along the way, and leaves without a mess.
What separates it from a typical gutter-cleaning outfit is what happens after the cleaning starts. Reviewers describe Jason spotting a loose bracket, a bent downspout, or a broken hanger mid-job and fixing it on the spot, sometimes at no extra charge — recent reviews describe extra repairs bundled into a routine cleaning, and in a 2025 review a customer described a gutter-guard installation that came with a couple of complimentary fixes. When a 2026 blizzard tore a gutter loose from one customer's house, a friend's referral got it reattached within days of the call; in a separate 2025 review, another customer described a similar bracket failure at a beach house getting new brackets installed three days after reaching out.
The company holds an active Massachusetts home improvement contractor registration (HIC #194359, registered to Jason Aleman) and has been reviewed on Google since at least 2021, with 39 reviews in the last six months and none of them negative. Communication comes up constantly in the reviews — text confirmations when booking, a heads-up when the crew is en route, and in a few cases photos of the finished gutters sent unprompted so a homeowner can see the work without climbing a ladder.
One thing worth knowing before booking: scheduling runs through an automated phone system. A 2025 reviewer said the AI voice initially put them off, though it worked fine once they were connected to a person — a heads-up for anyone expecting a live voice on the first call.
Gutter Cowboy is the right call for gutter maintenance and repair — routine cleanings, storm damage, loose brackets, clogged downspouts — rather than broader remodeling work; its home-improvement license covers more ground than the actual track record does, which is squarely gutters. Worth confirming before booking: whether a same-visit repair spotted during a cleaning gets billed separately or folded into the price, since reviews describe it going both ways.
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Most recent comments
5.0Sep 2, 2026
Great communication, fair pricing, and excellent service. They even unprompted sent a photo of our tallest gutter to prove it was clean!
I called Gutter Cowboy to see if I could get service and I was given an appointment for the very next day. The work was done when they said it was going to be done with complete professionalism and care. I'd highly recommend their service to anyone who needs attention given to their gutters.
Excellent service!!! Very happy with the Gutter Cowboy. Impressed with how he took pictures as he was cleaning my gutters to show exactly what was going on there. 10/10 recommend for all your gutter needs!
