What does a roof replacement cost in Greater Boston?
Typical Greater Boston range for this kind of work, from regional averages — not a quote from Kelly's Property Services. 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.
Long client tenures — customers describe returning for two decades
One 2025 complaint — condo owner alleged sloppy work and a safety lapse
Crew sizing on big jobs — that review blamed delays on thin crews
Lapsed Connecticut registration — BuildZoom lists it inactive since 2018
Forty-seven Google ratings averaging 4.8, and what the reviews keep doing is naming people — Dennis, Scott, Chris, Marcos, Alex — rather than the company.
Kelly's Property Services works out of 662 Moody Street in Waltham, with a second address in Southborough. The company says it was established in 1989 and has served Greater Boston, Middlesex County and MetroWest ever since; Bryan Kelly is its president. The Better Business Bureau puts it at 38 years with ten employees, has accredited it since October 2005, and grades it A+. Its Massachusetts home improvement contractor registration is active.
The bread and butter is condominium and larger-home exterior work: painting, windows, siding, roofs, decks and common areas. A property manager wrote in July 2026 about roughly fifteen years of projects across the condo associations they manage in southeastern Massachusetts. In March 2026 a homeowner described seven Marvin Ultimate windows going into the front of the house — a carpentry crew pulling and setting them, a painting crew finishing them inside and out. A July 2025 customer had a 30-year-old roof replaced and singled out the communication from Alex; a September 2025 condo owner had rotting clapboard repaired and a deck power-washed. Eight reviews have come in since February, none of them negative.
One account cuts the other way and deserves weight. In October 2025 a unit owner whose condo association signed a $2 million contract wrote a one-star review alleging sloppy carpentry, a schedule that slipped because crews were too small, a demolished deck left without a protective barrier outside a slider, a painter who worked without tarps and stained a stairwell carpet, and a foreman who was intimidating when they complained. A December 2025 reviewer wrote specifically to offset it. Both are worth reading before signing a large association contract — and worth turning into questions about crew size, schedule commitments and site protection.
One housekeeping note: BuildZoom's page for the company tracks a Connecticut home improvement registration recorded inactive since 2018, and scores the company zero on that basis. The Massachusetts registration is the one that governs work here, and it is active.
This is a call for condo boards and homeowners with a multi-trade exterior project — the kind of job where somebody has to coordinate painters, carpenters and a roof, and where the same project manager showing up every day is the point. For a large association job, get the crew count and the schedule in writing.
Heard around town
News & the web
Kelly's Property Services in Waltham, MA – Reviews, Hours, and Contact Details
“Kelly's performed an extensive exterior renovation for 17 townhomes. They were professional and had great workmanship. I would recommend them highly.”
Compliments to Kelly Services for the recent completed exterior renovation of our building on Admirals Way. Teams showed up daily and maintained a sense of order and competence amidst demolition, unexpected repairs, installation and finish work. They always showed respect and consideration for us and our home. Cleaned up at the end of the day and used safety fences to contain various materials. We appreciate project management and team leaders for their customer service and timely attention to our questions or concerns.
Mike Young was great as our painting project manager and the painting crew lead by Dani was efficient and professional. They finished five rooms including high ceilings in a day and a half.
This is a major assessment construction project in process. Whenever there is a project to remove existing material, there's always going to be repairs that's needed. In my interaction with the construction workers on this job site, they've been consistent, friendly and work hard to the their job at task and make any corrections/ modifications needed. All workers seem to be hardworking and knowledgeable. I really like to acknowledge Joe Muchulowski and Marcos Allerrandro for their hard work, knowledgeable wisdom and friendly attitudes. Also like to acknowledge Eduardo and his brother for doing good work. These guys are good contractors whom are doing many tasks at hand. Definitely recommend them and other workers for future reference, good day.
Chris M, Joesley, & Marcos were fantastic in assisting with a roof & ceiling issue in my home. All were professional & timely in dealing with a needed repair along with the general improvements being completed at my condominium complex. Thank you for a job well done!
Cannot say enough good things about Chris Marciano, Joesley And Marcos along with others with Kelly’s Property Services. They are amazing with their knowledge, response to homeowners, and their are hard work ethic. I have worked with them for months now and every day they present nothing but their best! Highly recommend!