Local roofing contractor offering repairs, replacements, roof ventilation work, and maintenance with an emphasis on clear communication and practical solutions.
Homeowners mention prompt scheduling, clear pricing, and thorough communication with photos before and after repairs. The company is noted for practical solutions without pressure to upsell. Workmanship on small repairs and vent installations is frequently highlighted.
Milton-based with projects in surrounding communities; call to confirm service to your location.
Roof leak diagnosis and repair, shingle replacement, roof ventilation and vent installs, roof replacement, eavestrough cleaning, and general roof maintenance.
Reviews consistently mention fast response times for repairs and clear, friendly communication, including photo updates. Many customers appreciate reasonable pricing and solutions focused on fixing the problem rather than pushing full replacements. Work quality on leak repairs, shingle fixes, and vent installations is praised. Several note punctual arrival and tidy work.
Excellent service - came within a day to fix a hole in the roof and also fixed up a few other problems at no added cost. Very friendly and communicated throughout the job with photos. Highly recommend.
We had a great experience with Sandy and Simon from Ollies Roofing. Simon installed 2 roof vents for us, and checked our roof to see if we had any other issues. His work was outstanding, communication was great throughout the process, and on top of that their pricing was extremely reasonable. Simon is genuinely a great person. We recommend them 100% and will definitely call them back from now on for anything roof related! What a great find!
Simon and Sandy were amazing!Sandy was a fount of knowledge when I was originally booking for an eaves trough cleaning.Simon went above and beyond to do a great job.Would recommend this team to everyone with a roof in Milton!
What a breath of fresh air. In a time when it feels like everyone—businesses, governments, and individuals—is trying to reach into your pocket, encountering someone like Simon is truly refreshing.We had leaks in our roof, and nearly every roofing company we contacted was quick to push for a full roof replacement—often before even inspecting the roof properly. Then came Simon.He arrived exactly when he said he would (a rarity these days), took the time to assess the situation thoroughly, and clearly laid out our options. He explained the likelihood of success with a repair versus a full replacement, along with the costs for each. No pressure, no upselling—just honest, informed advice.Simon came across as incredibly knowledgeable, but more importantly, he was genuine. This makes us feel a lot more confident in making a decision to get a new roof or repair. In today’s world, having someone transparently walk you through your options and costs is a true blessing.Any company that can retain someone of Simon’s caliber for so long must be doing something right. He’s truly a roof whisperer.
I recently had a great experience with Ollie’s Roofing that truly deserves recognition.After some heavy winds, a few shingles flew off my roof. I initially contacted another company (Toronto’s Choice Home Improvements), who quoted a couple hundred dollars. But once they arrived, they suddenly claimed there were more issues and refused to touch it for less than $3,000—a total scam.Thankfully, I reached out to Ollie’s Roofing, and from the start, Sandy was incredibly helpful and understanding. I was able to get an appointment within just 2 days. Simon came on site and was not only knowledgeable but also friendly and professional.Ollie’s has been around for 17 years, and I can absolutely see why. Their honesty, reliability, and customer-first approach really stood out. In a time when it’s hard to find trustworthy trades, Ollie’s Roofing is a breath of fresh air.I’ll definitely be contacting them for any future roofing needs—and I highly recommend them to anyone looking for quality work and peace of mind.
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