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At their annual Selling Season Kick-Off Breakfast held at the Oysterhead Lounge in Newcastle recently, the 30-plus associates from Cheney Insurance, Newcastle Realty, and Newcastle Vacation Rentals gathered to honor their clients, to welcome spring, and to celebrate the success of their companies, which together make up the Cheney Financial Group.

Area native Dennis Hilton of Newcastle has served as President and CEO of these Damariscotta-based service businesses for most of his career, and recently celebrated a significant milestone by reaching his 40th year work anniversary. A surprise staff luncheon was held recently, honoring the achievement.

Dennis Hilton, CEO
Cheney Financial Group
Dennis Hilton, CEO

“I began working for my parents at the insurance agency right after graduating Lincoln Academy in 1984,” explained Hilton. That launched a career as a local businessman and entrepreneur that has now spanned four decades.

During that time, Hilton helped grow the insurance operation by acquiring The Glidden Agency in 1998. He also negotiated the acquisition of Newcastle Square Realty in 1999 and merged that firm with a much smaller Cheney Realty Company. In 2002, Hilton purchased the former Damariscotta Hardware building and renovated that into the present Day-Nash Building on Main Street, Damariscotta. He spun off a vacation cottage rental division which has now operated for over 20 years as an independent company. “It is amazing how the years have flown by,” explained Hilton, “while we have continued to serve the insurance, real estate, and vacation cottage needs of hundreds of families.”

Over the years, Hilton has also launched several other businesses including Hilton Transport, West Neck Auto Storage, and Hilton Timber Management. “I enjoy the variety of my role and have had the great pleasure of working with some very amazing people at our companies,” added Hilton. “Our leadership team and staff make my job easier by doing their jobs exceptionally well, which makes for a smooth-running operation. I really love hearing feedback from our clients, which I receive routinely, having been born and raised right here in town and knowing many of our customers personally for many years.”

When asked what has provided the most satisfaction when reflecting on his tenure, Hilton is quick to mention the important work of the Cheney Financial Group Charitable Giving Committee. Established over 20 years ago, volunteer staff members manage the overall community support efforts and financial giving of the companies. “I am also proud of our legacy, going back to founder Ralph Cheney, his daughter Arlene and her husband Mac MacKechnie. They gave my parents a tremendous opportunity back in the late 1960’s, just like my parents did for me in the mid-1980’s. If not for them, I would not have been so fortunate to live and work in the communities I grew up in. I am forever grateful to them.”

Cheney Insurance is a fifth-generation family-owned business that is celebrating 70 years of service. Their office is located at 277 Main Street, Damariscotta and they can be reached at 207-563-3435. Newcastle Realty, with a staff of 20 real estate agents, is one of the largest realty firms in the area. They have offices at 87 Main Street, Damariscotta (207-563-1003) and 14 Todd Avenue in Boothbay Harbor (207-633-4433). Newcastle Vacation Rentals is based in Damariscotta and manages the seasonal rental activities for over 80 cottage and property owners on nearby lakes, ponds, rivers, and the ocean. They can be reached at 207-563-6500.