After more than four decades of service and stewardship, Dennis Hilton has officially passed the torch to the next generation of leadership at three of Lincoln County’s most respected family-owned businesses: Cheney Insurance, Newcastle Vacation Rentals, and Newcastle Realty.

The change marks a significant milestone in a local legacy that spans more than 70 years. Founded and nurtured by the Cheney, MacKechnie, and Hilton families, these businesses have long been cornerstones in midcoast Maine -- providing trusted insurance guidance, vacation rental management, and full-service residential real estate expertise that now extends to luxury homes, commercial properties, and business brokerage.

The new ownership group includes Dennis’ sons, Nathan Hilton and Chris Hilton, along with their wives, Jessica Hilton and Hannah Hilton, and longtime Chief Financial Officer Joe Ford. Hannah Hilton serves as chief operating officer across all three businesses, ensuring operational consistency and forward-looking leadership.

“This transition is deeply meaningful to our family,” said Dennis Hilton. “It’s rare today to see businesses passed from one generation to the next, let alone five. I have full confidence in this team -- they bring fresh perspective, energy, and a deep commitment to the communities we serve.”

Nathan and Chris, who also operate their own landscaping businesses, have both grown up surrounded by the family businesses. They express their gratitude for the opportunity and the responsibility they now carry.

“We are proud to continue the important services our family has been known for,” said Nathan Hilton. Added COO Hannah Hilton, “Our goal is to honor that history while continuing to evolve and serve our clients with the highest standards.

With locations in Damariscotta and Boothbay Harbor, the three companies operate independently but share a united mission: to serve Midcoast Maine with integrity, personal attention, and local insight. This generational handoff ensures that area residents and visitors will continue to experience the same trusted service they’ve come to expect—rooted in tradition but focused on the future.

Cheney Insurance is an independent insurance agency offering choice among many different insurance company partners. Their office is located at 277 Main Street, Damariscotta and they can be reached at 207- 563-3435. Newcastle Realty is one of the largest independent realty firms in the area with more than 20 agents. 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 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.