Ruppert Enters Ohio by Acquiring Five Seasons Landscape Management

What happened

Ruppert Landscape, a commercial landscaping company headquartered in Laytonsville, Maryland, announced on April 21, 2026 that it had acquired Five Seasons Landscape Management of Columbus, Ohio. The deal is Ruppert's entry into Ohio. Steve Woods, Five Seasons' co-owner, joins Ruppert as a partner and leader in the Columbus market. Financial terms were not disclosed.

The seller

Bill Leidecker founded Five Seasons in 1997, and Woods partnered with him shortly afterward and now leads the company. It serves Columbus and the surrounding metro area from an east branch and a west branch, and it works only for commercial clients: office parks, corporate campuses, HOA communities, medical facilities, retail centers and educational institutions across central Ohio. Landscape maintenance and snow and ice removal anchor the work, with irrigation, seasonal color, pond maintenance, and design and construction alongside. The company no longer takes on new residential customers, and it says it ranks among the top five commercial landscaping companies in central Ohio.

Since 2012 Five Seasons has run the business on BOSS, a web-based system that gives clients a portal showing scheduled and completed work, contracts and invoices.

"For nearly 30 years, Five Seasons has been built around our people, our customers, and doing things the right way," Woods said in the announcement. He added that "Ruppert's commitment to training and safety, creating career opportunities for their team, and their vision for continued growth in Columbus and throughout Ohio made this partnership a natural fit." The business still operates under the Five Seasons name, now as a Ruppert Landscape company.

The buyer

Knox Lane, a San Francisco growth-oriented investment firm, acquired a majority stake in Ruppert in December 2022, with founder Craig Ruppert and the management team keeping a significant investment. Ruppert employed more than 1,800 people across 30 branches at the time. It now reports more than 3,400 team members across the Northeast, Mid-Atlantic and Southeastern United States, and Five Seasons takes its footprint to 11 states and Washington, DC. Phil Key, president at the time of the Knox Lane deal, is now CEO.

"We are pleased to enter the Ohio market with a team that operates at such a high level," Key said. "The Five Seasons team brings tremendous experience, talent, and momentum."

How Ruppert structures its partnerships

Ruppert says it looks for maintenance-focused commercial landscape companies, with recurring maintenance at the core and enhancements as add-ons, and it describes a deal structure that lets sellers "take chips off the table" today while keeping a share of the equity upside. Its recent deals follow the same pattern on leadership. Ruppert announced Five Seasons five weeks after it announced the acquisition of Landscapes Unlimited in Wilmington, North Carolina, on March 17, 2026, a deal in which founder Todd McCabe joined Ruppert as a partner. In Nashville, brothers Mark and Mike Russell stayed on when Ruppert acquired Enviro-Scapes in August 2025. The Five Seasons release says Woods joins as a partner but does not say whether he rolled over equity. Owners weighing a sponsor-backed buyer can read our guide on selling a landscaping business to private equity.

What this means for landscaping owners

Five Seasons fits the commercial, maintenance-focused profile Ruppert publishes: commercial-only, maintenance-led with snow and ice as the winter line, and run by an operator who has been with the company since its first years. Ruppert's Ohio operation is the two branches Five Seasons already ran, under the Five Seasons name and with its co-owner leading the market. For commercial landscaping owners in central Ohio, a buyer now has the backing of a platform of more than 3,400 people, while its customers still see a local name and a local leader.

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 Ohio.

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Source: Ruppert Landscape - https://www.ruppertlandscape.com/ruppert-landscape-enters-ohio-market-with-acquisition-of-five-seasons-landscape-management/