Riddle landscaping

Riddle Landscaping is a one-person-and-crew operation out of Roslindale, run by Colby Riddle, and across 88 Google ratings averaging 4.9 the same pattern shows up again and again: people hire him for one yard job and keep him on for years. Condo associations and HOAs around South Boston and Dorchester use him for both landscaping and snow removal, and several reviewers describe standing, multi-year arrangements rather than a single visit. The last six months back that up with specifics. A condo board had an overgrown, densely planted city lot cleared and mulched on short notice; another client had a tree removed, perennials planted, beds mulched, and a lawn seeded in a single day, with Colby returning weeks later to check on it; a backyard was rebuilt with an expanded patio, new sod, a new tree, and a walkway. On the snow side, a South Boston condo board describes him and his crew returning twice mid-storm during a nearly two-foot dump to keep the property clear. What repeats across these isn't vague praise — it's people naming the specific job and saying it was finished the way it was scoped. There's one real crack worth asking about before booking: in June 2026 a customer said Colby damaged their creeping thyme, admitted it, and then refused to fix it. That's not a one-off — a similar complaint from the year before describes the same kind of plant destroyed during aeration in Dedham, plus a broken garden light and a promised replanting that never happened. Two complaints about the same kind of damage and the same failure to follow through is worth a direct conversation if you have plantings you care about. The company's own site and several directories agree on the footprint — Boston, Newton, Milton, South Boston, Chestnut Hill, and Brookline — and the service list: landscaping, lawn care, cleanups, hardscapes, and snow removal. One thing doesn't line up: outside directories describe the company as having over two decades of experience, but its BBB file was only opened in April 2026 and BBB doesn't yet have enough history to rate it — worth asking directly how long the operation has run under this name. For seasonal cleanups, everyday lawn care, or a standing snow-removal contract — particularly a condo association that wants one person to just handle it — this is a well-tested choice. If the job involves plants you don't want touched, get clear on what happens if something goes wrong.