City of Winchester Salaries above $50,000 As of March 2011, school system slalaries are not included. |
| Salary | Position | Hire Date | Salary | Position | Hire Date | |
| $145,000.00 | CITY MANAGER | 1/11/2010 | 58,676.80 | POLICE SERGEANT | 12/15/2001 | |
| 124,009.60 | CITY ATTORNEY | 10/24/2006 | 58,622.72 | FIREFIGHTER TECHNICIAN | 7/12/1989 | |
| 117,666.00 | PUBLIC SERVICES TEAM LEADER | 10/9/2006 | 57,907.20 | MASTER POLICE OFFICER | 3/18/1995 | |
| 113,760.00 | COMMONWEALTH ATTORNEY | 1/1/2002 | 57,907.20 | MASTER POLICE OFFICER | 2/25/1995 | |
| 111,821.00 | PLANNING/DEVELOP TEAM LEADER | 2/1/2001 | 57,616.00 | ASST SOCIAL SERVICES DIRECTOR | 4/24/1989 | |
| 104,421.00 | DEPUTY COMMONWEALTH ATTORNEY | 10/31/1988 | 57,241.60 | POLICE SERGEANT | 6/16/1998 | |
| 103,419.00 | CLERK OF THE CIRCUIT COURT | 6/1/1985 | 57,138.00 | ASSISTANT FINANCE DIRECTOR | 5/28/1996 | |
| 100,630.00 | HUMAN SERVICES TEAM LEADER | 3/1/2005 | 56,992.00 | OPERATIONS SUPERINTENDENT | 1/3/2011 | |
| 100,000.00 | POLICE CHIEF | 11/3/2008 | 56,929.60 | SHERIFF SERGEANT | 8/1/1998 | |
| 96,658.00 | INFORMATION TECH DIRECTOR | 10/20/1988 | 56,867.20 | MASTER POLICE OFFICER | 8/14/2006 | |
| 93,000.00 | EXEC DIRECTOR - SERVICE AUTH | 10/2/1989 | 56,828.72 | ASST COMM ATTORNEY I | 4/6/2004 | |
| 88,192.00 | FINANCE DIRECTOR | 6/30/1997 | 56,638.40 | DEPUTY SHERIFF III | 5/15/1995 | |
| 87,048.00 | FIRE & RESCUE CHIEF | 8/3/2010 | 56,576.00 | MASTER POLICE OFFICER | 5/25/1998 | |
| 86,050.00 | PUBLIC WORKS DIRECTOR | 7/28/1997 | 56,324.32 | FIRE & RESCUE SERGEANT | 8/15/1989 | |
| 85,322.00 | PLANNING DIRECTOR | 4/5/1988 | 56,284.80 | MASTER POLICE OFFICER | 6/16/1997 | |
| 81,033.47 | ASST COMM ATTORNEY III | 1/28/2008 | 55,931.20 | MASTER POLICE OFFICER | 2/21/2000 | |
| 80,309.00 | SENIOR COMPUTER PROGRAMMER | 8/7/1995 | 55,918.72 | FIRE & RESCUE SERGEANT | 10/8/1997 | |
| 80,000.00 | POLICE MAJOR | 10/15/1979 | 55,598.00 | ENGINEERING INSPECTOR | 9/15/1986 | |
| 79,165.00 | OPERATIONS SUPERINTENDENT | 7/20/1987 | 55,370.00 | ADMINISTRATIVE ASSISTANT II | 10/12/1977 | |
| 78,790.00 | SENIOR COMPUTER PROGRAMMER | 3/13/2006 | 55,296.80 | FIRE & RESCUE SERGEANT | 10/2/2000 | |
| 78,732.00 | CITY TREASURER | 1/1/1998 | 55,245.00 | DIRECTOR OF EMER COMMUNICATION | 8/26/1996 | |
| 76,398.00 | SUPERINTENDENT, JDC | 11/13/1997 | 55,000.00 | EXECUTIVE DIRECTOR - WPA | 9/15/2003 | |
| 76,190.40 | POLICE CAPTAIN | 7/29/1995 | 54,995.20 | EXEC DIRECTOR - WFCCVB | 11/29/2004 | |
| 73,661.00 | SHERIFF | 1/1/2002 | 54,864.16 | FIREFIGHTER TECHNICIAN | 2/23/1987 | |
| 72,966.00 | PARKS AND RECREATION DIRECTOR | 7/10/2000 | 54,600.00 | ASST FIRE MARSHAL | 5/14/2001 | |
| 72,034.00 | COMMISSIONER OF THE REVENUE | 1/1/2010 | 54,431.52 | FIRE & RESCUE SERGEANT | 5/31/1998 | |
| 69,992.00 | INTERIM ADMIN DIRECTOR | 4/19/2004 | 54,059.20 | POLICE SERGEANT | 1/22/2001 | |
| 69,326.40 | POLICE CAPTAIN | 5/25/1992 | 54,028.94 | PARALEGAL/OFFICE ADMINISTRATOR | 7/3/1989 | |
| 67,184.00 | ZONING & INSPECTIONS ADMIN | 7/3/2006 | 53,643.00 | PLANNER II | 7/30/2001 | |
| 66,830.40 | FIRE & RESCUE CAPTAIN | 10/15/1990 | 53,580.80 | MASTER POLICE OFFICER | 2/28/2000 | |
| 65,811.20 | POLICE CAPTAIN | 1/11/2001 | 53,512.16 | FIRE & RESCUE SERGEANT | 2/17/2003 | |
| 64,396.80 | ASSISTANT SUPERINTENDENT, JDC | 10/27/1997 | 53,469.00 | ASST COMM ATTORNEY I | 3/13/2006 | |
| 64,230.40 | POLICE LIEUTENANT | 1/6/1996 | 53,331.20 | POLICE SERGEANT | 9/21/2002 | |
| 64,168.00 | POLICE LIEUTENANT | 6/8/1996 | 53,227.00 | CHIEF DEPUTY TREASURER | 8/17/1987 | |
| 63,897.60 | FIRE & RESCUE CAPTAIN | 6/5/1997 | 52,998.40 | MASTER POLICE OFFICER | 5/22/2000 | |
| 62,212.80 | POLICE LIEUTENANT | 2/9/2002 | 52,665.60 | MASTER POLICE OFFICER | 6/7/1999 | |
| 62,046.00 | BUILDING OFFICIAL | 4/26/1993 | 52,538.72 | FIREFIGHTER TECHNICIAN | 7/15/2002 | |
| 61,975.68 | FIRE & RESCUE LIEUTENANT | 8/24/1988 | 52,499.00 | FOSTER CARE COORDINATOR | 12/3/2007 | |
| 61,609.60 | POLICE LIEUTENANT | 1/23/2001 | 52,431.65 | VICTIM WITNESS DIRECTOR | 10/26/1994 | |
| 61,609.60 | POLICE LIEUTENANT | 6/15/2002 | 52,353.60 | MASTER POLICE OFFICER | 5/22/2000 | |
| 61,543.04 | FIRE & RESCUE LIEUTENANT | 11/29/1986 | 52,079.04 | FIREFIGHTER TECHNICIAN | 12/6/2001 | |
| 61,443.20 | MASTER POLICE OFFICER | 3/27/1993 | 52,000.00 | ENGINEER I | 1/19/2009 | |
| 61,402.00 | FACILITY MANAGER | 9/6/2005 | 52,000.00 | PROTECTIVE SVCS TEAM COOR | 9/12/2000 | |
| 61,360.00 | MASTER POLICE OFFICER | 10/28/1989 | 51,970.88 | FIREFIGHTER TECHNICIAN | 2/26/2001 | |
| 60,840.00 | FIRE & RESCUE LIEUTENANT | 10/3/1994 | 51,854.00 | SR CODE COMPLIANC INSPEC/PO II | 1/6/1990 | |
| 60,840.00 | POLICE SERGEANT | 2/25/1995 | 51,484.16 | FIREFIGHTER TECHNICIAN | 9/11/1995 | |
| 60,632.00 | CITY ENGINEER | 2/7/2005 | 51,403.04 | FIRE & RESCUE SERGEANT | 1/26/2004 | |
| 60,353.28 | FIRE & RESCUE SERGEANT | 10/15/1990 | 51,396.80 | POLICE SERGEANT | 12/24/2001 | |
| 60,237.00 | WEBMASTER | 1/2/2008 | 51,001.60 | DETENTION SPECIALIST SUPERVISR | 5/3/1999 | |
| 59,946.00 | FACILITY MANAGER | 3/1/2006 | 50,537.76 | FIRE & RESCUE SERGEANT | 2/7/1999 | |
| 59,426.00 | SPECIAL PROJECT COORDINATOR II | 4/5/1980 | 50,148.80 | POLICE SERGEANT | 12/27/2003 | |
| 58,974.24 | FIRE & RESCUE LIEUTENANT | 4/27/1998 | 50,132.16 | FIREFIGHTER TECHNICIAN | 5/28/1997 | |
| 58,968.00 | FACILITY MANAGER | 9/19/2005 | 50,107.00 | ECC LEAD COMM SPECIALIST | 11/29/1999 | |
| 58,802.00 | EXEC DIRECTOR - OTDB | 4/5/2004 | ||||