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Roof Right Now Boston is an Allston shingle-roofing company built around Jonathan Dunn, the point of contact named in nearly every one of its reviews going back to 2021. The company describes itself as a GAF-certified installer of asphalt shingle roofing across Greater Massachusetts and southern New Hampshire. The consistent thread across five years of reviews is a fast, personal first response: Jonathan showing up the same day or next to look at storm damage, giving a clear price, and often beating competing bids by thousands of dollars. Multiple reviewers describe crews that finish quickly and clean up thoroughly, with one 2024 customer calling the finished roof and its 50-year warranty the last one they'll ever need to buy. In a November 2025 r/bostonhousing Reddit thread, a commenter said Roof Right Now Boston did a great job on theirs and was on time for visits, responsive and super fast from start to finish. Two more recent accounts complicate that picture. A 2025 reviewer said the finished roofing work was excellent but that once the deposit was paid, communication got harder — the person who'd handled the quote handed off to someone else after the contract was signed. A 2024 reviewer said it took about a year for the company to pull the required permit, and that a gutter installed alongside the new roof used the wrong-sized extension piece and had to be replaced two years later. Massachusetts lists its home improvement contractor registration, 196396, as expired. For a straightforward roof replacement, Roof Right Now Boston has a long run of specific, positive accounts and a well-liked point of contact in Jonathan. Given the more recent complaints about post-contract follow-through and the expired registration, it's worth confirming current licensing and getting the permit and gutter details in writing before signing.
“Roof Right Now Boston did a great job on ours. They were on-time for visits, responsive and super fast from start to finish.”
We had old leaky gutters with broken hangers and many layers of brushed in tar. Could never get them to stop leaking. Jonathan came up with a very fair price and hung new ones. His team did a great job replacing 120 year old fascia boards and toping them with new gutters. They cleaned up afterwards and left us all very happy!!! Highly recommend them.
The quality of the work itself was excellent, but be prepared to advocate for yourself once the company has your deposit. The process started off well—Bob, who provided our quote, was professional and helpful. However, after signing the contract, communication shifted to Jonathan, and that’s when things became challenging. I had to follow up multiple times just to get basic updates, including reaching out to my town myself to check on the permit status. Even after the roof was completed, I’ve had to follow up four times for a receipt or proof of work—and I still haven’t received a response. If you choose this company, know that you may need to manage the project details and communication on your own. The work is good, but once they’ve secured your business, you may not be their priority
Jonathan called me back within 2-3 minutes of using the estimation widget- they focus on shingle roofs and I have a slate roof but he VERY kindly used his Google earth-enabled tool to ballpark the number of squares (the unit of measure for roofing costs) on my roof, and he explained a few other inputs about my roofing materials. I appreciate him taking a few minutes out of his day to look up the info for me so that I am better equipped for conversations with slate roofers.
Roof is holding up well. It took them a year to finally pull the permit, but they did. Jonathan also had gutters installed, but we've since had to have them replaced (2 years later). They used a 6 inch extension piece instead of a correctly sized gutter piece and it was tilting in the wrong direction.
Jonathan and his team are true professionals. The quality of the roof, the clean-up of the debris and the quick turnaround was outstanding. The roof looks incredible and the 50 year warrantee makes this the last roof I'll ever buy. But most importantly, my 5 star rating stemmed from the superior communication! Jonathan always made himself available for a question, concern, an idea or even a tax reimbursement question. My wife and I couldn't be happier - thank you Jonathan, Jamie and the entire team for a great experience.
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2 changes recorded — last scanned Jul 2, 2026.
Typical Greater Boston range for this kind of work, from regional averages — not a quote from Roof Right Now Boston. 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
Seven skylight replacements in one day5.0
Answers in a storm5.0
Detailed craftsmanship5.0
Long-running family businessNot yet rated
Long-lasting roofs4.3
