| Year | REALTOR® | Associate | Rising Star | Strategic Partner | Good Neighbor | Patricia Ortsiefen Lifetime Award | Managing Broker | New Member of the Year |
| 2023 | Jude Offerle | Erik Sager | Ethan Nagar | Mark Kolar | Chris Stephens | Juan Dietz | ||
| 2022 | Brad Andersen | Ethan Nagar | Jamie Dunsing | Betsy Brint | Connie Conway | |||
| 2021 | Chris Stephens | Gina Tarpey | Jeffery Marks | Brad Andersen | Marilyn Glazer | |||
| 2020 | Joel Raynes | Travis Wallace | Brian Jessen | |||||
| 2019 | Steve Hudson | Melanie Peel | Dotty Dose | |||||
| 2018 | Bill Coduto | Luke Mutter | Denise Edenhofer | |||||
| 2017 | Carrie Healy | Timothy Shaker | Kim Chalekian | |||||
| 2016 | Eve Bremen | Dominick Clarizio | Michael Gordon | |||||
| 2015 | Allyson Hoffman | Judy Ann Bruce | Ari Aberman | |||||
| 2014 | Georgia Pierini | Erik Gimbel | Erin Marcus | |||||
| 2013 | Keith Hancock | Diana Karouzos | Carol Merz | |||||
| 2012 | Doug Ayers | Pauline Wehr | Aaron Masliansky | |||||
| 2011 | Darla Terrell | Carrie Healy | ||||||
| 2010 | Kris Keller | Haley Hwang | Ron Isaacson | |||||
| 2009 | Maureen Mohling | Ann Trandai | ||||||
| 2008 | Gary Jensen | Debbie Hymen | Fred Feinstein, McDermott | |||||
| 2007 | Patricia Ortseifen | Kathy Pinkus | Kevin Kete | |||||
| 2006 | Lisa Hathaway | Emery Moorehead | Tamara McHugh | |||||
| 2005 | Leslie Stein | Tom Rebarchak | Brian Jessen | |||||
| 2004 | Scott Lackie | Georgia Pierini | C. Bryce Fuller | Jeff Nathan | ||||
| 2003 | Jean Wright | Allyson Hoffman | Henry Apfelbach | |||||
| 2002 | Herb Walbaum | Laurie Tierney | Diane Falk | |||||
| 2001 | Roxane Malo | Dolores Sharlot | Helene O'Hara | |||||
| 2000 | Marge Hawk | Keith Hancock | ||||||
| 1999 | Dan Schermerhorn | Jill Bohrnell | ||||||
| 1998 | Nick Marino | Mary June Saboto | Carol McGregor | Carol Lord | ||||
| 1997 | Jean George | Susan Kelly | ||||||
| 1996 | Susan Cooney | Dan Phillips | Wayne Jacobson | Peggy Cunniff | ||||
| 1995 | Ray Anderson | Cas Obie | Jill Bohrnell | |||||
| 1994 | Connie Conway | Harvy Hoffman | Diane Huggins | Merrill Henry | ||||
| 1993 | Joe Goodman | Barbara Roseman | Margaret Semrad | |||||
| 1992 | David Robin | Robert Johnston | ||||||
| 1991 | Richard Nash, III | Ray Garard | ||||||
| 1990 | Ben Gerstman | Robert Brooks | ||||||
| 1989 | Chris Eigel | Martha Brand | ||||||
| 1988 | Allen Schmidt | Jean George | ||||||
| 1987 | Patricia Ortseifen | Elizabeth Howe | ||||||
| 1986 | Marilyn Glazer | Dee Malmsten | ||||||
| 1985 | Phill Leekley | Connie Sanford | ||||||
| 1984 | George Hall, III | Dorothy Riegel | ||||||
| 1983 | Theodore Riley | Susan Cooney | ||||||
| 1982 | Henry Zander, III | Nick Snyder | ||||||
| 1981 | Ruth Thiel | Daina McGuire | ||||||
| 1980 | William Walsh | Sue V. Hall | ||||||
| 1979 | Alan Ramsay | Marliyn Glazer | ||||||
| 1978 | Lou Pfaff | Joan Manierre | ||||||
| 1977 | Justine & Herbert Kahn | Diana Hunt | ||||||
| 1976 | Neil King | Joan Westfall | ||||||
| 1975 | Lois K. Steward | Barbara Barth | ||||||
| 1974 | Robert McGuire | George Hall, III |
