| $350,000–1 million | AIKENS CORPORATION | WINCHESTER, VA | United Bank |
| $350,000–1 million | AMERICAN SERVICES GROUP, INC | WINCHESTER, VA | EagleBank |
| $350,000–1 million | AMHERST FAMILY PRACTICE PC | WINCHESTER, VA | Atlantic Union Bank |
| $2–5 million | ANNANDALE MILLWORK AND ALLIED SYSTEMS CORPORATION | WINCHESTER, VA | United Bank |
| $150,000–350,000 | ANS PROPERTY LLC | WINCHESTER, VA | Pacific Premier Bank |
| $150,000–350,000 | APPLE BLOSSOM FAMILY PRACTICE | WINCHESTER, VA | United Bank |
| $150,000–350,000 | APPLE VALLEY ANIMAL HOSPITAL | WINCHESTER, VA | Bank of Clarke |
| $350,000–1 million | APPLE VALLEY SCALE COMPANY INC | WINCHESTER, VA | United Bank |
| $350,000–1 million | BARRETT INDUSTRIES INC. | WINCHESTER, VA | Atlantic Union Bank |
| $150,000–350,000 | BLUE DUCK LLC | WINCHESTER, VA | LendingClub Bank, National Association |
| $150,000–350,000 | BLUE RIDGE HABITAT FOR HUMANITY, INC | WINCHESTER, VA | First Bank |
| $2–5 million | BLUE RIDGE HOSPICE, INC. | WINCHESTER, VA | Bank of Clarke |
| $1–2 million | BLUE RIDGE INDUSTRIES, INC. | WINCHESTER, VA | First Bank |
| $150,000–350,000 | BLUE RIDGE LANDSCAPE AND DESIGN, INC. | WINCHESTER, VA | First Bank |
| $150,000–350,000 | BOHNENKAMP ENTERPRISES INC | WINCHESTER, VA | First Bank |
| $350,000–1 million | BONE & JOINT SPECIALISTS OF WINCHESTER PC | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | BRADDOCK ST UNITED METHODIST CHURCH | WINCHESTER, VA | First Bank |
| $150,000–350,000 | BRIAN OMPS TOWING & REPAIR LLC | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | BRIDGING THE GAPS, INC. | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | BUCHBAUER & MCGUIRE, PC | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | BUETTNER TIRE DISTRIBUTORS LLC | WINCHESTER, VA | FNB Bank, Inc. |
| $150,000–350,000 | C & S SNYDER TRUCKING INC | WINCHESTER, VA | United Bank |
| $150,000–350,000 | C&D VADEN INC | WINCHESTER, VA | Bank of Clarke |
| $1–2 million | CAR CREDIT NATION INC | WINCHESTER, VA | Truist Bank |
| $350,000–1 million | CARING ANGELS HOME HEALTH LLC | WINCHESTER, VA | United Bank |
| $350,000–1 million | CARROLL CONSTRUCTION, CO. | WINCHESTER, VA | First Bank |
| $150,000–350,000 | CASZONE LLC | WINCHESTER, VA | Blue Ridge Bank, National Association |
| $150,000–350,000 | COMPASSIONATE HOME CARE LLC | WINCHESTER, VA | United Bank |
| $150,000–350,000 | CONSOLIDATED ELECTRIC SERVICE LLC | WINCHESTER, VA | Wells Fargo Bank, National Association |
| $150,000–350,000 | CONVENANT BUILDING MAINTENANCE INC | WINCHESTER, VA | First Bank |
| $150,000–350,000 | CWNZ LLC | WINCHESTER, VA | Itria Ventures LLC |
| $150,000–350,000 | DATALUX CORPORATION | WINCHESTER, VA | Truist Bank |
| $150,000–350,000 | DIRECT TITLE SOLUTIONS, INC. | WINCHESTER, VA | Truist Bank |
| $150,000–350,000 | DR. TERRY SINCLAIR HEALTH CLINIC, INC | WINCHESTER, VA | Bank of Clarke |
| $350,000–1 million | DREAMACHINES, INC. | WINCHESTER, VA | Truist Bank |
| $350,000–1 million | EASTERN SUPPLY INC | WINCHESTER, VA | Burke and Herbert Bank and Trust Company |
| $150,000–350,000 | ECHOHILL ENTERPRISES, INC. | WINCHESTER, VA | Blue Ridge Bank, National Association |
| $350,000–1 million | EVANGELICAL COUNCIL FOR FINANCIAL ACCOUNTABILITY | WINCHESTER, VA | Burke and Herbert Bank and Trust Company |
| $150,000–350,000 | EYE ASSOCIATES OF WINCHESTER INC | WINCHESTER, VA | First Bank |
| $350,000–1 million | F J INDUSTRIAL EQUIPMENT LEASING, LLC | WINCHESTER, VA | United Bank |
| $350,000–1 million | FABRITEK COMPANY INC | WINCHESTER, VA | First Bank |
| $150,000–350,000 | FAIRBROOK WINCHESTER, LLC | WINCHESTER, VA | Burke and Herbert Bank and Trust Company |
| $350,000–1 million | FELLOWSHIP BIBLE CHURCH | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | FITZGERALD EXCAVATING & CONSTRUCTION, INC. | WINCHESTER, VA | First Bank |
| $350,000–1 million | FOODSOURCE, LLC | WINCHESTER, VA | First Bank |
| $350,000–1 million | FORBIDDEN FRUIT LLC | WINCHESTER, VA | BMO Bank National Association |
| $150,000–350,000 | FORT COLLIER ENTERPRISES LLC | WINCHESTER, VA | Atlantic Union Bank |
| $350,000–1 million | FREDERICK BLOCK CO., INC. | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | FURLONG'S SHEETMETAL, INC. | WINCHESTER, VA | First Bank |
| $350,000–1 million | G.W. MOTORS INC | WINCHESTER, VA | Truist Bank |
| $350,000–1 million | GARBER ICE CREAM CO. INC. | WINCHESTER, VA | United Bank |
| $350,000–1 million | GIOVANNI P. IUCULANO D.D.S. P.C. | WINCHESTER, VA | First-Citizens Bank & Trust Company |
| $350,000–1 million | GLASS-GLEN BURNIE MUSEUM INC | WINCHESTER, VA | United Bank |
| $150,000–350,000 | GLORY DAYS GRILL OF WINCHESTER LLC | WINCHESTER, VA | Sandy Spring Bank |
| $150,000–350,000 | GLS PLUMBING INC | WINCHESTER, VA | United Bank |
| $150,000–350,000 | GREEN VALLEY COMMONS, INC | WINCHESTER, VA | First Bank |
| $350,000–1 million | GREENWAY ENGINEERING INC | WINCHESTER, VA | Burke and Herbert Bank and Trust Company |
| $150,000–350,000 | GUARDIANLIGHT OF NORTHWESTERN VA INC | WINCHESTER, VA | Bank of Clarke |
| $1–2 million | H & W CONSTRUCTION CO INC | WINCHESTER, VA | United Bank |
| $2–5 million | H N FUNKHOUSER & CO | WINCHESTER, VA | United Bank |
| $1–2 million | HIVA, INC | WINCHESTER, VA | CIBC Bank USA |
| $150,000–350,000 | HOTTEL & WILLIS, P.C. | WINCHESTER, VA | Atlantic Union Bank |
| $2–5 million | HOWARD SHOCKEY & SONS, INC | WINCHESTER, VA | First Bank |
| $150,000–350,000 | HUNT COUNTRY HEALTH SERVICES, INC. | WINCHESTER, VA | Navy FCU |
| $150,000–350,000 | INSTRULOGIC LLC | WINCHESTER, VA | Atlantic Union Bank |
| $150,000–350,000 | INSURANCE CENTER OF WINCHESTER, INC | WINCHESTER, VA | Bank of Clarke |
| $2–5 million | INTEGRITY HOME MORTGAGE CORPORATION | WINCHESTER, VA | The First Bank and Trust Company |
| $150,000–350,000 | INTERNAL MEDICINE CONSULTANTS | WINCHESTER, VA | Burke and Herbert Bank and Trust Company |
| $350,000–1 million | J.D. MATTHEWS AND ASSOCIATES, L.C. | WINCHESTER, VA | First-Citizens Bank & Trust Company |
| $350,000–1 million | JADE TREE LLC | WINCHESTER, VA | United Bank |
| $150,000–350,000 | JESARA CORP. | WINCHESTER, VA | First United Bank & Trust |
| $150,000–350,000 | JNO. S. SOLENBERGER & CO. INC | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | JOHNNY BLUE INC. | WINCHESTER, VA | Bank of Clarke |
| $350,000–1 million | KEE CONSTRUCTION SERVICES, INC | WINCHESTER, VA | First Bank |
| $350,000–1 million | KERN MOTOR COMPANY, INC. | WINCHESTER, VA | Truist Bank |
| $150,000–350,000 | KIDWELL FENCING & HOME IMPROVEMENTS, INC. | WINCHESTER, VA | The Capon Valley Bank |
| $350,000–1 million | LANTZ CONSTRUCTION CO. OF WINCHESTER, INC. | WINCHESTER, VA | Atlantic Union Bank |
| $150,000–350,000 | LIFETIME TOOL & BUILDING PRODUCTS LLC | WINCHESTER, VA | Bank of Charles Town |
| $150,000–350,000 | LTD OF WINCHESTER | WINCHESTER, VA | Blue Ridge Bank, National Association |
| $150,000–350,000 | LUCKY 7, LP, LLC | WINCHESTER, VA | United Bank |
| $350,000–1 million | LYLE P STROSNYDER, INC | WINCHESTER, VA | Blue Ridge Bank, National Association |
| $1–2 million | MALLOY AUTOMOTIVE OF WINCHESTER LLC | WINCHESTER, VA | United Bank |
| $350,000–1 million | MALLOY CHEVROLET CADILLAC, LLC | WINCHESTER, VA | United Bank |
| $150,000–350,000 | MALLOY COLLISION CENTER, LLC | WINCHESTER, VA | United Bank |
| $1–2 million | MALLOY WINCHESTER, LLC | WINCHESTER, VA | United Bank |
| $150,000–350,000 | MANE ATTRACTION ENTERPRISES LLC | WINCHESTER, VA | Bank of Charles Town |
| $150,000–350,000 | MARSH & LEGGE LAND SURVEYORS PLC | WINCHESTER, VA | Truist Bank |
| $1–2 million | MILLER AUTO SALES INC | WINCHESTER, VA | United Bank |
| $150,000–350,000 | MILLER MACHINE & TOOL COMPANY, INC. | WINCHESTER, VA | The Grant County Bank |
| $350,000–1 million | MOHR INFORMATION & INVESTIGATIVE SERVICES LLC | WINCHESTER, VA | Bank of Clarke |
| $150,000–350,000 | MY THREE SONS, INC. | WINCHESTER, VA | Truist Bank |
| $350,000–1 million | MYPOTENTIAL VIRGINIA LLC | WINCHESTER, VA | First Bank |
| $150,000–350,000 | N & L ENTERPRISE LLC | WINCHESTER, VA | Bank of America, National Association |
| $2–5 million | NATIONAL FRUIT PRODUCT CO., INC. | WINCHESTER, VA | The First Bank and Trust Company |
| $350,000–1 million | NAVITUS ENGINEERING INC | WINCHESTER, VA | Burke and Herbert Bank and Trust Company |
| $150,000–350,000 | NEUROLOGIC ASSOCIATES PLC | WINCHESTER, VA | United Bank |
| $350,000–1 million | NEW HORIZONS PROFESSIONAL ABA SERVICES INC. | WINCHESTER, VA | Bank of Clarke |
| $350,000–1 million | NL ENTERTAINMENT, LLC | WINCHESTER, VA | Virginia National Bank |
| $350,000–1 million | NORTH STEPHENSON, INC. | WINCHESTER, VA | United Bank |
| $150,000–350,000 | NVVA-WINCHESTER LLC | WINCHESTER, VA | Atlantic Union Bank |