| Year | REALTOR® | Rookie | Strategic Partner |
| 2009 | Maureen Mohling | ||
| 2008 | Gary Jensen | Fred Feinstein, McDermott | |
| 2007 | Patricia Ortseifen | Kevin Kete | |
| 2006 | Lisa Hathaway | Tamara McHugh | |
| 2005 | Leslie Stein | Brian Jessen | |
| 2004 | Scott Lackie | C. Bryce Fuller | Jeff Nathan |
| 2003 | Jean Wright | Henry Apfelbach | |
| 2002 | Herb Walbaum | Diane Falk | |
| 2001 | Roxane Malo | Helene O'Hara | |
| 2000 | Marge Hawk | ||
| 1999 | Dan Schermerhorn | ||
| 1998 | Nick Marino | Carol McGregor | Carol Lord |
| 1997 | Jean George | ||
| 1996 | Susan Cooney | Wayne Jacobson | Peggy Cunniff |
| 1995 | Ray Anderson | Jill Bohrnell | |
| 1994 | Connie Conway | Diane Huggins | Merrill Henry |
| 1993 | Joe Goodman | Margaret Semrad | |
| 1992 | David Robin | ||
| 1991 | Richard Nash, III | ||
| 1990 | Ben Gerstman | ||
| 1989 | Chris Eigel | ||
| 1988 | Allen Schmidt | ||
| 1987 | Patricia Ortseifen | ||
| 1986 | Marilyn Glazer | ||
| 1985 | Phill Leekley | ||
| 1984 | George Hall, III | ||
| 1983 | Theodore Riley | ||
| 1982 | Henry Zander, III | ||
| 1981 | Ruth Thiel | ||
| 1980 | William Walsh | ||
| 1979 | Alan Ramsay | ||
| 1978 | Lou Pfaff | ||
| 1977 | Justine & Herbert Kahn | ||
| 1976 | Neil King | ||
| 1975 | Lois K. Steward | ||
| 1974 | Robert McGuire |
