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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
Prestige Roofing is a Medway, Massachusetts roofing contractor run by owner Lennie Lombardo. The company says Lennie's roofing work began in 1999, and its listed work includes residential and commercial roofing, roof repairs, gutters, chimney flashing, and siding repairs. Homeowners consistently describe prompt communication, competitive and fair pricing, professional crews, careful preparation and cleanup, and fast roof replacements. Reviews cover complete reroofing, decking and shingle replacement, skylights, ice-dam and storm repairs, chimney flashing, gutters, fascia, and siding. The business has 104 reviews collected from 2021 through 2026, including 20 in the last six months; Google shows 4.9 stars from 124 ratings, while BBB lists an A+ grade and accreditation. There is one detailed one-star review describing poor communication, arriving without tools, requesting use of the homeowner's items, and damage to a crawlspace door. That complaint is materially at odds with the much larger body of positive reviews, but it is worth asking how the company handles access, protection of property, and dissatisfied-customer follow-up. BBB's listed services also include flat roofing, metal roofing, gutter guards, gutter replacement, shingle roofing, siding repairs, and chimney flashing repair. Prestige appears best suited to homeowners seeking a responsive roofing company for replacement, repair, weather-related work, skylights, or related exterior repairs. Before booking, confirm the exact scope, materials, schedule, cleanup and property-protection plan, and how any change or warranty issue will be handled.
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!
Lennie’s team did an outstanding job of replacing my roof’s decking and shingles. They did it in 1 day. The yard was left as they had found it. The price was very fair and the whole process was zero stress. This the second job Prestige has done for me and I plan to use them again.
We recently had a new roof installed by PRESTIGE ROOFING, and we couldn't be happier with the entire experience. From the very beginning, Lennie was professional, thorough, and knowledgeable. He even climbed up a ladder to personally inspect the roof before preparing the estimate. The estimate itself was detailed and easy to understand, with a complete scope of work and a helpful diagram outlining the project. The roofing crew was courteous, hardworking, and clearly experienced. They worked efficiently, kept the job site organized, and it was obvious they took pride in their workmanship. Best of all, the project was completed on schedule and exactly within the agreed budget, with no surprises. We highly recommend Prestige Roofing to anyone looking for a quality roofing contractor. Their professionalism, attention to detail, and excellent customer service made the entire process smooth and stress free.
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1 change recorded — last scanned Sep 8, 2026.
Broad remodeling scope3.3
Quick roof turnarounds with no mess left5.0
State-verified Home Improvement Contractor license5.0
Honest diagnosis over upselling repairs5.0
Siding restoration4.3
Fast scheduling4.6
Same-day roof jobs4.6