1994 Joan Cusack – C21/Classic Properties
1995 Jerry Jacknow – Jacknow Real Estate
1996 Nancy Leavy – F.C. Pilgrim & Company
1997 Pat Stout – F.C. Pilgrim & Company
1998 Geri McLauchlan – Merrill Becker, Knoll & Assoc.
1999 Tom Cusack – C21/Classic Properties
2000 John Gasa – Baird & Warner
2001 Gary Mancuso – C21/Classic Properties
2002 Carl Schwebl – Reich & Becker
2003 Dorothy Reid – Baird & Warner
2004 Pete Salerno (posthumously) – Salerno
2005 Anne Ferri – F.C. Pilgrim
2006 Joe Langley – Re/Max in the Village
2007 Dan Bogojevich – Prudential Premier
2008 Marjorie Greenwald – Gloor Realty
2009 Cliff Osborn – Prudential Premier
2010 Alisa Coghill – Prudential Premier
2012 John Lawrence – Weichert/Nickel Group
2014 Catherine Deam (posthumously) – Gloor Realty Company
2016 Laura Maychruk – Gullo & Associates
2017 Jonathan Zivojnovic – River Elm Properties
2018 Gabe Caporale – Caporale Realty Group
2019 Kay Costello – Gagliardo Realty Associates LLC
2020 Jeanette Madock – Berkshire Hathaway HomeServices
2021 Kimberly Wojack – Baird & Warner
2023 Bethany Alexander – Baird & Warner