O’Leary Landscaping

O'Leary Landscaping has been serving Harwich, Chatham and Brewster with design, construction, hardscape and irrigation work — the company recently merged with Lower Cape Irrigation to round out that side of the business, and says it's been doing this since 1980 (BBB dates the company's start to 1998; the exact founding year is worth confirming). One customer's 2025 review says they've used the company for over 20 years and still count on it for regular home maintenance. Another, from 2023, described a specific fix: a builder had left too much fill on the property, causing basement flooding, and O'Leary regraded the yard and repitched a walkway and patio to send rainwater away from the house — at what the homeowner called a fair price. In a 2016 review, a customer called the crew thorough, punctual and meticulous, and noted they also handle winter plowing for the Cape Cod Theatre Company. The company carries an Angie's List Super Service Award from 2015 and 2016 and holds an A+ BBB grade. Its Houzz listing shows a landscape license number, though that hasn't been independently verified against the state registry — worth asking about directly. There's also some inconsistency about who currently runs the business: BBB names Sean M. O'Leary as president, while the company's own website credits ownership to Dan O'Leary — good to clarify who you'd be working with. Between the drainage fix, the long-tenured customer, and the hardscape and masonry work in its portfolio, this reads as a full-service Cape Cod outfit worth calling for anything from routine lawn care to a patio or retaining wall project.