| $150,000–350,000 | 3D CLEANING OF VIRGINIA, INC | WINCHESTER, VA | Bank of Clarke County |
| $150,000–350,000 | AIDS RESPONSE EFFORT, INC. | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $350,000–1 million | AIKENS CORPORATION | WINCHESTER, VA | United Bank |
| $150,000–350,000 | AIR BOSS, LLC | WINCHESTER, VA | Capital One, National Association |
| $150,000–350,000 | ALEXIS MIERZWA, P.L.C. | WINCHESTER, VA | Live Oak Banking Company |
| $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 County |
| $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 | Radius Bank |
| $150,000–350,000 | BLUE HORSE CARRIERS INC | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $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 County |
| $1–2 million | BLUE RIDGE INDUSTRIES, INC. | WINCHESTER, VA | First Bank |
| $150,000–350,000 | BLUE RIDGE LANDSCAPE AND DESIGN | WINCHESTER, VA | First Bank |
| $150,000–350,000 | BMB MANAGEMENT, INC. | WINCHESTER, VA | Citizens Bank, National Association |
| $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 County |
| $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 County |
| $150,000–350,000 | BRIAR OAK INVESTMENTS III, LLC | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | BRIDGING THE GAPS, INC. | WINCHESTER, VA | Bank of Clarke County |
| $150,000–350,000 | BUCHBAUER & MCGUIRE, PC | WINCHESTER, VA | Bank of Clarke County |
| $150,000–350,000 | BUETTNER TIRE DISTRIBUTORS LLC | WINCHESTER, VA | FNB Bank, Inc. |
| $350,000–1 million | BYTE SYSTEMS, LLC | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | C&D VADEN INC | WINCHESTER, VA | Bank of Clarke County |
| $150,000–350,000 | C&S SYNDER TRUCKING, INC. | WINCHESTER, VA | United Bank |
| $1–2 million | CAR CREDIT NATION INC | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $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 |
| $350,000–1 million | CROSSROADS COUNSELING CENTER, INC. | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | CWNZ, LLC | WINCHESTER, VA | Customers Bank |
| $150,000–350,000 | DATALUX CORPORATION | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $350,000–1 million | DERMATOLOGY ASSOCATES INC | WINCHESTER, VA | Atlantic Union Bank |
| $150,000–350,000 | DIRECT TITLE SOLUTIONS, INC. | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | DR. TERRY SINCLAIR HEALTH CLINIC, INC | WINCHESTER, VA | Bank of Clarke County |
| $350,000–1 million | DREAMACHINES, INC. | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $350,000–1 million | EASTERN SUPPLY INC | WINCHESTER, VA | Summit Community Bank, Inc. |
| $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 | Summit Community Bank, Inc. |
| $150,000–350,000 | EYE ASSOCIATES OF WINCHESTER INC | WINCHESTER, VA | First Bank |
| $350,000–1 million | F J INDUSTRIAL INC | WINCHESTER, VA | United Bank |
| $350,000–1 million | FABRITEK COMPANY INC | WINCHESTER, VA | First Bank |
| $150,000–350,000 | FAIRBROOK WINCHESTER, LLC | WINCHESTER, VA | Summit Community Bank, Inc. |
| $350,000–1 million | FELLOWSHIP BIBLE CHURCH | WINCHESTER, VA | Bank of Clarke County |
| $150,000–350,000 | FITZGERALD EXCAVATING & CONSTRUCTION, INC. | WINCHESTER, VA | First Bank |
| $350,000–1 million | FOODSOURCE, LLC | WINCHESTER, VA | First Bank |
| $150,000–350,000 | FOOT & ANKLE CENTER, PC | WINCHESTER, VA | Readycap Lending, LLC |
| $350,000–1 million | FORBIDDEN FRUIT LLC | WINCHESTER, VA | BMO Harris Bank National Association |
| $150,000–350,000 | FORT COLLIER ENTERPRISES | WINCHESTER, VA | Atlantic Union Bank |
| $150,000–350,000 | FRED L GLAIZE, LC | WINCHESTER, VA | Mid-Atlantic Farm Credit, ACA |
| $350,000–1 million | FREDERICK BLOCK CO., INC. | WINCHESTER, VA | Bank of Clarke County |
| $150,000–350,000 | FURLONG'S SHEETMETAL, INC. | WINCHESTER, VA | First Bank |
| $350,000–1 million | G.W. MOTORS INC | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $350,000–1 million | GARBER ICE CREAM CO. INC. | WINCHESTER, VA | United Bank |
| $150,000–350,000 | GAURAV AGARWAL DDS, MSD, PLLC | WINCHESTER, VA | Blue Ridge Bank, National Association |
| $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 | Summit Community Bank, Inc. |
| $150,000–350,000 | GUARDIANLIGHT OF NORTHWESTERN VA INC | WINCHESTER, VA | Bank of Clarke County |
| $350,000–1 million | GW LEASING, LLC | WINCHESTER, VA | Atlantic Union Bank |
| $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 County |
| $2–5 million | INTEGRITY HOME MORTGAGE CORPORATION | WINCHESTER, VA | The First Bank and Trust Company |
| $150,000–350,000 | INTERNAL MEDICINE CONSULTANTS | WINCHESTER, VA | Summit Community Bank, Inc. |
| $150,000–350,000 | INTERSTATE TRUCK SERVICE, INC. | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | J R SOLENBERGER INC | WINCHESTER, VA | Bank of Clarke County |
| $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 County |
| $150,000–350,000 | JOHNNY BLUE INC. | WINCHESTER, VA | Bank of Clarke County |
| $350,000–1 million | KEE CONSTRUCTION SERVICES, INC | WINCHESTER, VA | First Bank |
| $350,000–1 million | KERN MOTOR COMPANY, INC. | WINCHESTER, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $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 |