| $2–5 million | WESTMINSTER-CANTERBURY OF WINCHESTER, INC | WINCHESTER, VA | First Bank |
| $150,000–350,000 | WHITE PROPERTIES OF WINCHESTER INC | WINCHESTER, VA | United Bank |
| $150,000–350,000 | WILLIAMS MAINTENANCE OF WINCHESTER, INC. | WINCHESTER, VA | Atlantic Union Bank |
| $1–2 million | WINCHESTER ANESTHESIOLOGISTS, INC. | WINCHESTER, VA | First Bank |
| $350,000–1 million | WINCHESTER BUILDING SUPPLY CO INC | WINCHESTER, VA | United Bank |
| $1–2 million | WINCHESTER CARDIOLOGY & VASCULAR MEDICINE PC | WINCHESTER, VA | First-Citizens Bank & Trust Company |
| $150,000–350,000 | WINCHESTER CHURCH OF GOD | WINCHESTER, VA | Bank of Clarke County |
| $350,000–1 million | WINCHESTER COMMUNITY MENTAL HEALTH CENTER, INC. | WINCHESTER, VA | IncredibleBank |
| $1–2 million | WINCHESTER EQUIPMENT CO | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | WINCHESTER EYE SURGERY CENTER LLC | WINCHESTER, VA | United Bank |
| $350,000–1 million | WINCHESTER GASTROENTEROLOGY ASSOCIATES, P.L.C. | WINCHESTER, VA | First-Citizens Bank & Trust Company |
| $150,000–350,000 | WINCHESTER HOTEL PARTNERS III LP | WINCHESTER, VA | Manufacturers and Traders Trust Company |
| $350,000–1 million | WINCHESTER INTERNAL MEDICINE | WINCHESTER, VA | First-Citizens Bank & Trust Company |
| $350,000–1 million | WINCHESTER METALS, INC. | WINCHESTER, VA | Bank of Clarke County |
| $350,000–1 million | WINCHESTER NEUROLOGICAL CONSULTANTS INC | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | WINCHESTER OBSTETRICS AND GYNECOLOGY, PLC | WINCHESTER, VA | First Bank |
| $350,000–1 million | WINCHESTER OPEN MRI, LLC | WINCHESTER, VA | Atlantic Union Bank |
| $150,000–350,000 | WINCHESTER ORAL SURGERY CENTER PC | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $350,000–1 million | WINCHESTER ORTHOPAEDIC ASSOCIATES, LTD. | WINCHESTER, VA | First Bank |
| $350,000–1 million | WINCHESTER PEDIATRIC CLINIC PC | WINCHESTER, VA | Bank of Clarke County |
| $150,000–350,000 | WINCHESTER PLUMBING & GAS SERVICES INC | WINCHESTER, VA | United Bank |
| $350,000–1 million | WINCHESTER PRINTERS INC | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $350,000–1 million | WINCHESTER PULMONARY & INTERNAL MEDICINE ASSOCIATES, PC | WINCHESTER, VA | Bank of Clarke County |
| $1–2 million | WINCHESTER RADIOLOGISTS, P.C. | WINCHESTER, VA | Atlantic Union Bank |
| $150,000–350,000 | WINCHESTER WOMEN'S SPECIALISTS, P.C. | WINCHESTER, VA | First Bank |
| $150,000–350,000 | WOODBINE FARMS, INC. | WINCHESTER, VA | The First Bank and Trust Company |
| $350,000–1 million | WWG MANAGEMENT SERVICES LLC | WINCHESTER, VA | Bank of Charles Town |
| $2–5 million | YOUNT HYDE & BARBOUR PC | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |