Winterberry Gardens Enters Maine by Acquiring Willie C. & Sons Landscaping

What happened

Winterberry Gardens, a landscape design, construction and maintenance company in Southington, Connecticut, has acquired Willie C. & Sons Landscaping LLC of Topsham, Maine. The deal closed March 24, 2026, and gives Winterberry a foothold in Maine. Nick Cloutier, Willie C.'s president, is staying on with the business.

Brookside Capital Partners provided subordinated debt and a preferred equity co-investment in Winterberry to support the acquisition. The purchase price and the size of that financing were not disclosed.

The seller

Willie Cloutier founded Willie C. & Sons in 2004, starting with residential landscaping and lawn care. His sons, Nick and Joe, worked in the business doing maintenance for local homeowners, and Nick now runs it. The company handles residential and commercial maintenance, design and construction across Midcoast and Southern Maine, from Brunswick and Harpswell south through Portland to Scarborough and Windham.

Most of its work is design-build. It designs and installs paver patios, hardscaping and outdoor kitchens in-house and guarantees hardscape work for three years. Alongside that it offers maintenance, fine gardening, lawn care with tick and mosquito barrier treatments, and commercial snow and ice removal. In 2025 it widened its service area and its offerings, adding tree and shrub care and ice and snow removal among them.

On the coast, the company stands out for handling regulatory work itself. It manages permitting on its own projects, including shoreland zoning permits and Maine Department of Environmental Protection permit-by-rule filings, and holds DEP certification in erosion control best practices. Its crews include certified arborists and certified pesticide applicators.

"We are excited to partner with Winterberry and believe they are the ideal organization to build upon the legacy Willie C. & Sons has established, while continuing to provide outstanding service to our customers and new opportunities for our employees," Nick Cloutier said.

The buyer

Brothers Scot and Al Leavitt founded Winterberry Gardens in 1985, and by 2025 it had a team of more than 240 people. It offers landscape design and installation, irrigation, lighting, lawn care, fertilization and property maintenance to residential and commercial clients, and it also builds golf-course irrigation. In 2025, chief executive Bryan Stolz called that "our fastest growing segment."

Winterberry became a portfolio company of Gemini Investors through a recapitalization in October 2024. Gemini is a Wellesley, Massachusetts, firm founded in 1993. It invests in lower-middle-market companies and has backed more than 180 businesses, in areas including business services, consumer products, manufacturing and health care.

"We believe Willie C. represents a compelling opportunity for Winterberry to further expand its footprint across New England while partnering with a talented leader in Nick Cloutier," said Michelle E. Kornack, vice president of Gemini Investors.

What this means for landscaping owners

When Gemini described the deal, it put two things in one sentence: more of New England for Winterberry, and Nick Cloutier. For an owner, the second is the instructive part. Willie C.'s specialties, design-build hardscaping, and the shoreland and DEP permitting behind it, are handled in-house, and the person running the company is the founder's son. Its president stayed on after closing, and the sponsor's statement presented him as part of the opportunity. An owner can read this deal as a sponsor-backed buyer counting the operator as part of what it bought. Owners weighing that kind of sale can read our guide on selling a landscaping business to private equity.

OffDeal is an advisory firm that helps lower-middle-market business owners sell with confidence. Reach out to learn more about our expertise with landscaping businesses in Maine.

Own a landscaping business with $5M–$100M in revenue? We’re glad to give you an honest read on what it’s worth and who would buy it — no pitch, no pressure. Get a free valuation.

Source: Hartford Business Journal - https://hartfordbusiness.com/article/southingtons-winterberry-gardens-expands-into-maine-after-private-equity-investment