Stephen Messina

Stephen was introduced to Ludlow when his sister, Suzanne Garvey, married and made Ludlow home. Originally from Newport, RI, Stephen’s career as an insurance operations executive has predominantly kept him in the southeast. Stephen has fond memories of visits to Ludlow, skiing Okemo with family, and enjoying the lakes and overeating at Mama [...]

Stephen was introduced to Ludlow when his sister, Suzanne Garvey, married and made Ludlow home. Originally from Newport, RI, Stephen’s career as an insurance operations executive has predominantly kept him in the southeast. Stephen has fond memories of visits to Ludlow, skiing Okemo with family, and enjoying the lakes and overeating at Mama Valente’s.


Stephen has a BS in Accounting from the University of Rhode Island and a Master of Business Administration from St. Leo University. Stephen spent 15 years with Progressive Insurance in a variety of roles as the carrier grew from obscurity to a Fortune 100 Company. For the past ten years he has been with a family-owned entity in Florida, where he has served as VP of Claims, Division President, and currently serves as the Chief Claims Officer and SVP of Insurance Operations.                         

           
A couple of years ago Stephen purchased a condo on Okemo and has been splitting time between Tampa, FL and Ludlow. Whether it be skiing, mountain biking, hiking, water sports, or riding his motorcycle through the mountains, he enjoys the outdoors and the beauty of Vermont. Stephen brings his legal and finance expertise to the MWD team and looks forward to carrying on its storied legacy of matching families with their dreams!

Office Location

  • Main Office
  • Ludlow Shopping Plaza
  • 213 Main Street, Suite 3
  • Ludlow, VT 05149

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