| $350,000–1 million | NW WORKS, INC. | WINCHESTER, VA | Truist Bank |
| $350,000–1 million | O'MALLEY AUTO GROUP, LLC | WINCHESTER, VA | JPMorgan Chase Bank, National Association |
| $150,000–350,000 | OAK STONE PIZZA LLC | WINCHESTER, VA | Primis Bank |
| $150,000–350,000 | OAK WISE INC | WINCHESTER, VA | Wells Fargo Bank, National Association |
| $150,000–350,000 | OMPS FUNERAL HOME INC | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | ORCHARDCREST APARTMENTS | WINCHESTER, VA | Virginia National Bank |
| $150,000–350,000 | PAINTER-LEWIS PLC | WINCHESTER, VA | First Bank |
| $150,000–350,000 | PAPERMILL PLACE INC | WINCHESTER, VA | Bank of Clarke |
| $350,000–1 million | PARSONS & PARSONS LC | WINCHESTER, VA | Jefferson Security Bank |
| $350,000–1 million | PARTLOW INSURANCE AGENCY, INC. | WINCHESTER, VA | United Bank |
| $150,000–350,000 | PATRIOT COLLISION CENTER, LLC | WINCHESTER, VA | FNB Bank, Inc. |
| $150,000–350,000 | PATRIOT FIRE AND SECURITY, LLC | WINCHESTER, VA | Bank of Clarke |
| $350,000–1 million | PEDIATRIC ASSOCIATES OF WINCHESTER, P.C. | WINCHESTER, VA | First Bank |
| $1–2 million | PERRY ENGINEERING COMPANY, INC. | WINCHESTER, VA | United Bank |
| $150,000–350,000 | PICCADILLY STREET LLC | WINCHESTER, VA | Bank of Clarke |
| $350,000–1 million | PINNACLE SERVICES WINCHESTER INC | WINCHESTER, VA | Truist Bank |
| $150,000–350,000 | PLANET FITNESS CHESAPEAKE LLC | WINCHESTER, VA | Bank of America, National Association |
| $150,000–350,000 | POWER CONCEPTS, INC. | WINCHESTER, VA | United Bank |
| $150,000–350,000 | PRESTIGE G, LLC | WINCHESTER, VA | United Bank |
| $350,000–1 million | PRK DRILLING & BLASTING INC | WINCHESTER, VA | City National Bank of West Virginia |
| $150,000–350,000 | QUALITY AUTO PARTS, LLC | WINCHESTER, VA | SouthState Bank National Association |
| $2–5 million | R & R REINFORCING, INC. | WINCHESTER, VA | Bank of Clarke |
| $2–5 million | R&L FOODS, LLC | WINCHESTER, VA | City National Bank |
| $350,000–1 million | R&R REINFORCING NJ, INC | WINCHESTER, VA | Bank of Clarke |
| $350,000–1 million | RAPPAHANNOCK PETROLEUM LLC | WINCHESTER, VA | United Bank |
| $350,000–1 million | READING LANDSCAPES, INC. | WINCHESTER, VA | First Bank |
| $150,000–350,000 | RENAL PHYSICIAN ASSOCIATES OF WINCHESTER | WINCHESTER, VA | Blue Ridge Bank, National Association |
| $150,000–350,000 | RETINA ASSOCIATES, PC | WINCHESTER, VA | First-Citizens Bank & Trust Company |
| $150,000–350,000 | RUGS DIRECT HOLDINGS LLC | WINCHESTER, VA | Truist Bank |
| $150,000–350,000 | RUTHERFORD & JOHNSON, P.C. | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | S&J ENTERPRISES, LL.C. | WINCHESTER, VA | First Bank of Owasso |
| $350,000–1 million | SACRED HEART OF JESUS CHURCH | WINCHESTER, VA | Truist Bank |
| $350,000–1 million | SAFFORD WINCHESTER, LLC | WINCHESTER, VA | Truist Bank |
| $1–2 million | SCHENCK FOODS COMPANY, INC | WINCHESTER, VA | United Bank |
| $150,000–350,000 | SCHROCK, INC. | WINCHESTER, VA | United Bank |
| $1–2 million | SELMA MEDICAL ASSOCIATES INC | WINCHESTER, VA | Burke and Herbert Bank and Trust Company |
| $150,000–350,000 | SHADE EQUIPMENT CO INC | WINCHESTER, VA | Truist Bank |
| $1–2 million | SHENANDAOH VALLEY DISTRIBUTING COMPANY INC. | WINCHESTER, VA | Truist Bank |
| $150,000–350,000 | SHENANDOAH EMERGENCY PHYSICIANS, PC | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | SHENANDOAH HEAD & NECK SPECIALISTS PLC | WINCHESTER, VA | Bank of Clarke |
| $350,000–1 million | SHENANDOAH ONCOLOGY PC | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | SHENANDOAH REFRIGERATION INC | WINCHESTER, VA | Truist Bank |
| $150,000–350,000 | SHENANDOAH SMILES PC | WINCHESTER, VA | First Bank |
| $350,000–1 million | SHINE TRANSPORTATION INC., | WINCHESTER, VA | FNB Bank, Inc. |
| $150,000–350,000 | SHOCKEY MANAGEMENT COMPANY | WINCHESTER, VA | First Bank |
| $350,000–1 million | SIMBECK, INC. | WINCHESTER, VA | Fountainhead SBF LLC |
| $150,000–350,000 | SMARTECH COMMUNICATIONS, LLC | WINCHESTER, VA | United Bank |
| $150,000–350,000 | SMILES OF VIRGINIA FAMILY DENTAL CENTER PLLC | WINCHESTER, VA | Itria Ventures LLC |
| $350,000–1 million | SOUTHERN STATES WINCHESTER COOPERATIVE | WINCHESTER, VA | CoBank ACB |
| $350,000–1 million | SPECIALMADE GOODS & SERVICES, INC. | WINCHESTER, VA | Truist Bank |
| $150,000–350,000 | TECH TEAM SOLUTIONS, LLC | WINCHESTER, VA | First Bank |
| $150,000–350,000 | THE FLOOR SHOP OF WINCHESTER, INC | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | THE SCHOOL @ SHARON'S LLC | WINCHESTER, VA | The Capon Valley Bank |
| $1–2 million | THE VILLAGE AT ORCHARD RIDGE INC | WINCHESTER, VA | First Bank |
| $150,000–350,000 | THE VIRGINIAN INC | WINCHESTER, VA | United Bank |
| $150,000–350,000 | THE WINCHESTER GROUP, INC. | WINCHESTER, VA | First Bank |
| $150,000–350,000 | TOTAL REMODELING SYSTEMS LLC | WINCHESTER, VA | Truist Bank |
| $150,000–350,000 | TRUE SELECT, LLC | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | UNCLE SAM TRANSPORTATION LLC | WINCHESTER, VA | Wells Fargo Bank, National Association |
| $150,000–350,000 | UROLOGY CLINIC OF WINCHESTER, PC | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | VALLEY BIOMEDICAL PRODUCTS AND SERVICES, INC. | WINCHESTER, VA | The First Bank and Trust Company |
| $150,000–350,000 | VALLEY CYCLE CENTER INC | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | VALLEY HOSPITALISTS, PC | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | VALLEY PAIN CONSULTANTS INC | WINCHESTER, VA | First-Citizens Bank & Trust Company |
| $150,000–350,000 | VILLAGE SQUARE RESTAURANT, LLC | WINCHESTER, VA | Truist Bank |
| $350,000–1 million | VIQ MEDIA TRANSCRIPTION INC. | WINCHESTER, VA | BMO Bank National Association |
| $350,000–1 million | VIRGINIA BRAIN AND SPINE CENTER, INC. | WINCHESTER, VA | First-Citizens Bank & Trust Company |
| $150,000–350,000 | VIRGINIA HEALTHCARE SERVICES OF THE VALLEY, LLC | WINCHESTER, VA | MainStreet Bank |
| $350,000–1 million | VIRGINIA RIGGERS, INC | WINCHESTER, VA | First Bank |
| $150,000–350,000 | VIRGINIA VISION THERAPY CENTER, INC | WINCHESTER, VA | First Bank |
| $350,000–1 million | WEN-ALEX, INC. | WINCHESTER, VA | Cadence Bank |
| $150,000–350,000 | WEST OAKS FARM, LLC | WINCHESTER, VA | Atlantic Union Bank |
| $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 |
| $350,000–1 million | WINCHESTER COMMUNITY MENTAL HEALTH CENTER, INC. | WINCHESTER, VA | IncredibleBank |
| $1–2 million | WINCHESTER EQUIPMENT CO | WINCHESTER, VA | Truist Bank |
| $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 |
| $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 |
| $350,000–1 million | WINCHESTER NEUROLOGICAL CONSULTANTS INC | WINCHESTER, VA | Truist Bank |
| $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 |
| $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 |
| $150,000–350,000 | WINCHESTER PLUMBING & GAS SERVICES INC | WINCHESTER, VA | United Bank |
| $350,000–1 million | WINCHESTER PRINTERS INC | WINCHESTER, VA | Truist Bank |
| $350,000–1 million | WINCHESTER PULMONARY & INTERNAL MEDICINE ASSOCIATES, PC | WINCHESTER, VA | Bank of Clarke |
| $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 |
| $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 |