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Prestige Roofing is a roofing company based in Medway, MA, managed by owner Lennie Lombardo. Its website says it has been in business 27 years, offers free estimates and is insured. One recent customer found the company through their town's Facebook group, and the entire roof was completed in just one day, with the yard left spotless. Another recent job replaced a roof's decking and shingles in one day, and Lennie climbed a ladder to inspect a roof before preparing a detailed estimate with a diagram. Prestige also installed 3 new skylights after a request to troubleshoot a leak, with a perfect match to the existing shingle color, and replaced a tough piece of aluminum siding along with ridge caps and bathroom fan vent covers. Ice damming was looked at the next day and fixed within a week. A 2023 review of a siding project described repeated delays, too little material ordered, gutter guards that were never received and Lennie threatening to pull out of the project. A one-star 2026 review reads: "Showed up with no tools and demanded to use my personal items. Broke my crawlspace door too."
Prestige Roofing under the management of Lennie Lombardo is one of the best experiences I have ever had working with a contractor. He is a hard working professional who is prompt, thorough, efficient and very easy to work with. Lennie does not waste your time and does not try to sell you anything more than you need or want. He is honest and very competitively priced. The end result is excellent. Thank you Prestige for making this such a positive experience from start to finish.
Prestige Roofing was great! They did two homes for me, the crew was excellent, nice work and the site cleaned up when they were done. I highly recommend them John M
Great experience working with Prestige on my new roof. They fit me into their schedule timely and did a great job. Project was done on time and on budget.
Quality work done and very helpful determining where the leak was coming from which is wasn’t easy
We couldn’t be happier with our experience with Prestige Roofing! Before choosing a company, I asked for recommendations in our town’s Facebook group, and Prestige Roofing was recommended over and over again. Now I completely understand why. Their quote was very competitive, they got us scheduled quickly, and the entire roof was completed in just one day. The crew was professional, hardworking, and respectful of our property throughout the process. They used high-quality materials, and the finished roof looks amazing. What impressed us just as much was the cleanup. They left our yard spotless, taking the time to make sure everything was picked up before they left. From pricing and communication to workmanship and cleanup, Prestige Roofing exceeded our expectations. I highly recommend them to anyone looking for a roofing company they can trust!
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1 change recorded — last scanned Sep 28, 2026.
Typical Greater Boston range for this kind of work, from regional averages — not a quote from Prestige Roofing. Use it to sanity-check bids, then get the real number in writing.
A square is 100 sq ft of roof surface — bigger than the floor plan because of pitch and overhangs.
Estimated range
$9,000 – $18,600
Typical roofing project around $13,800
