Verified record
Typical Greater Boston range for this kind of work, from regional averages — not a quote from Kilraine & Son 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
Kilraine & Son Roofing has been putting Tom's name on jobs around Westwood for what the company says is 52 years, dating back to 1974 — though the Better Business Bureau's own file for the company shows it was started in 2011, so the two accounts of how long it's been around don't quite line up. What isn't in dispute is the volume of detailed, specific praise the crew has earned over the past several years. In a late-2025 review, one customer called the team thorough, efficient and reliable after Tom replaced her elderly mother's roof; another spring-2025 review described a four-day job that stripped a house down, sided it, and installed new gutters, with neighbors commenting on how the house looked afterward. A 2024 reviewer said a vinyl siding job finished a day ahead of schedule with strong craftsmanship, and reviews from 2022 and 2023 describe repeat customers calling Tom back across multiple properties. One 2021 review described hiring the company three separate times — a flashing leak repair, then a full roof replacement, then exterior painting with new gutters — because each job impressed enough to bring them back. Two more recent, undated reviews on the company's BBB page cut against that picture sharply: one accuses the crew of taking items from a property and reacting angrily when asked to return them, and another says the reviewer wouldn't call Kilraine for a new roof because the company was already responsible for damage on the house. Neither complaint appears anywhere else in the record, but they're serious enough to ask about directly before signing anything, along with getting a straight answer on how long the current business has actually been operating. For a full roof replacement, siding job, or gutter work in the Westwood area, the bulk of the written record — even though it's a few years old in most cases — points to a crew that does complete, thorough work and finishes on time. Just go in with those two BBB complaints and the ownership-history question in hand.
“But the roof turns out beautiful, the debris gets cleared away, and the house with its new chapeau never looked so sophisticated.”
Kilraine and their crew were fantastic to work with. Tom went above and beyond when replacing my elderly mother’s roof. Thorough, efficient and reliable are the best ways to describe them!
Very pleased with the finished product. Many people have commented how beautiful the house looks. Tom's grew worked super hard, long days completely stripped the house, applied backer board, sided and installed new gutters and cleaned up after in just four days. We highly recommend Kilraine & Son.
Kilraine And Son just finished up vinyl siding on my house. What an incredible transformation. They finished the job a day earlier than estimated. This team was full on hard working, and great quality of work and craftsmanship.
Kilraine + Son’s exceeded our exceptions with the massive transformation of our home. I really appreciated there suggestions which we did + were amazing. There craftsmanship is of excellence. There on time - anything extra I added was done immediately. I highly recommend Kilraine + Son’s for any project.
Tom has done work at several of our investment properties and has always done an outstanding job. I highly recommend Kilraine & Son!
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Certified attributes are verified against the public registry. Others are the business's own statement.
1 change recorded — last scanned Sep 5, 2026.
Project range4.6
Garage framing — 2024 customer cites quality work and exact scheduling3.7
State-verified Home Improvement Contractor license5.0
Honest diagnosis over upselling repairs5.0
Full roof jobs finished in a day4.6
Renovation scope4.5