Shelton's DiMatteo Insurance partners with Cross Insurance 

DiMatteo Insurance of Shelton is now affiliated with Cross Insurance, one of the largest independent insurance providers in the country. 

Headquartered in Bangor, Me., branch manager Kim DiMatteo of Bethany said this new partnership enables DiMatteo Insurance to broaden its market opportunities, including expanded personal and commercial lines in New England and throughout the country.

Kim DiMatteo started working in the family insurance business in 1991 and specializes in commercial insurance, specifically construction, contractors and real estate. 

DiMatteo Insurance will continue to meet our client’s insurance needs with the veteran leadership, outstanding staff, and high customer service standards that have been the hallmark of our family business since its founding in 1960,” said DiMatteo. “Our agency handles all lines of business including employee benefits.” 

Previously referred to as DiMatteo Group, the business has spun off into three divisions: DiMatteo Insurance overseen by Kim DiMatteo of Bethany; DiMatteo Financial LLC, headed up by Kim’s husband, John DiMatteo, of Bethany; and DiMatteo Tax and Accounting, managed by Rosemarie Esposito of Shelton.

Other family members involved in the business include Loretta Lesko of Shelton, who is a partner in the tax business as well as a training supervisor in the insurance division. Her husband, Robert Lesko, specializes in insurance sales and is also a partner in the tax division. A total of 25 employees from all the divisions will remain located at 79 Bridgeport Avenue, Shelton.    

“We see many synergies with this new partnership,” said DiMatteo, ”and are thrilled to join the Cross Insurance family of agencies. We both have a long tradition as family-owned businesses. This new arrangement is mutually beneficial. Our thousands of customers will continue to be handled by the same local account managers and producers.” 

DiMatteo Insurance will carry on its year-round philanthropic work and will still support local charities through the DiMatteo Family Charitable Foundation. In fact, DiMatteo Insurance will be a top gold sponsor of their Foundation. 

The Foundation was established more than 14 years ago as a tribute to their founder and late father Anthony “Tony” DiMatteowho was battling cancer at the time. Since then, the Foundation has contributed more than $376,000 for various well-known local and national charities that fund research, education and finding a cure for diseases. 

“We will spearhead our numerous community projects as we have for several decades," said Kim DiMatteo. "Specifically, we will organize our Annual Golf Tournament, the 'Under the Tree' Program of BHcare in Ansonia, and the Annual Easter Basket Drive to benefit the Norwalk Emergency Center, Domestic Violence Crisis Center and Inspirica.”   

For more than 25 years, Kim DiMatteo has been involved in the community as a member, board member and officer with the Home Builders and Remodelers Association of Fairfield County (HBRA). In 2017, she was inducted into the Fairfield County Hall of Fame by HBRA. She currently serves as its first vice president and will be named president of HBRA in 2020. 

Cross Insurance, its privately held parent company, is a family owned and operated insurance firm with three generations actively involved in the day-to-day operation. Founded in 1954, Cross Insurance has more than 40 offices located throughout Maine, Massachusetts, New Hampshire, Connecticut and Rhode Island.

The company has grown to become one of New England’s largest independent insurance intermediaries and the nation’s 33rd largest broker of U.S. Business, with more than 40 branches and more than 800 employees. Each office has a full staff of personal and business insurance professionals.  

Cross Insurance represents the region’s largest network of carefully selected suppliers which includes some of the largest national carriers in the industry, as well as New England’s leading regional insurance carriers.  Cross represents a total of 150 insurance providers, which enhances the company’s ability to satisfy the varied insurance needs of major employers and individuals alike. 

Visit DiMatteo Insurance’s new website at  for more information or call 203-924-4811.