| $150,000–350,000 | PIERCE'S PITT BAR-B-QUE | WILLIAMSBURG, VA | Chesapeake Bank |
| $350,000–1 million | PITTMAN CHRYSLER CORP. WILLIAMSBURG CHRYSLER JEEP DODGE | WILLIAMSBURG, VA | The Old Point National Bank of Phoebus |
| $150,000–350,000 | PRAXTON ENTERPRISES, INC. | WILLIAMSBURG, VA | Atlantic Union Bank |
| $150,000–350,000 | PRECARIOUS BEER LLC | WILLIAMSBURG, VA | Chesapeake Bank |
| $350,000–1 million | PRESTON H ROBERTS, INC. | WILLIAMSBURG, VA | Citizens and Farmers Bank |
| $350,000–1 million | PRIORITY AUTOMOTIVE WILLIAMSBURG, INC. | WILLIAMSBURG, VA | Towne Bank |
| $350,000–1 million | PRISM CONTRACTORS & ENGINEERS, INC | WILLIAMSBURG, VA | The Old Point National Bank of Phoebus |
| $150,000–350,000 | PROLABOR FREIGHT HANDLING INC | WILLIAMSBURG, VA | Newport News Shipbuilding Empl CU Inc d/b/a BayPort CU |
| $150,000–350,000 | PROTECTION BY DESIGN INC | WILLIAMSBURG, VA | The Old Point National Bank of Phoebus |
| $150,000–350,000 | PROVIDENCE CLASSICAL SCHOOL, INC | WILLIAMSBURG, VA | Atlantic Union Bank |
| $350,000–1 million | REALTEC COMMUNITY SERVICES | WILLIAMSBURG, VA | Towne Bank |
| $150,000–350,000 | RENTAL STORES LLC | WILLIAMSBURG, VA | Towne Bank |
| $150,000–350,000 | RHINO 6984 INC | WILLIAMSBURG, VA | Chesapeake Bank |
| $350,000–1 million | ROBERT F. MORRISON, DMD, PC | WILLIAMSBURG, VA | The Old Point National Bank of Phoebus |
| $150,000–350,000 | SAM E. ENGLISH II DDS LLC | WILLIAMSBURG, VA | Atlantic Union Bank |
| $350,000–1 million | SAUMIER, INC. | WILLIAMSBURG, VA | Towne Bank |
| $150,000–350,000 | SERVICE METAL FABRICATORS INC | WILLIAMSBURG, VA | The Old Point National Bank of Phoebus |
| $150,000–350,000 | SHEPHERD SECURITY SERVICES LLC | WILLIAMSBURG, VA | Sonabank |
| $150,000–350,000 | SINON INC | WILLIAMSBURG, VA | Village Bank |
| $350,000–1 million | SOHO ARLINGTON TRS LLC | WILLIAMSBURG, VA | Fifth Third Bank |
| $150,000–350,000 | SOTHERLY HOTELS, LP | WILLIAMSBURG, VA | Village Bank |
| $2–5 million | ST BEDE CATHOLIC CHURCH | WILLIAMSBURG, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | STARLING GUTTERING, INC. | WILLIAMSBURG, VA | Towne Bank |
| $150,000–350,000 | STAT SERVICES, INC. | WILLIAMSBURG, VA | Towne Bank |
| $150,000–350,000 | STEVEN STENSLAND DDS PC | WILLIAMSBURG, VA | PNC Bank, National Association |
| $150,000–350,000 | TAM CONSULTANTS, INC. | WILLIAMSBURG, VA | Chesapeake Bank |
| $350,000–1 million | TEK FUSION GLOBAL INC | WILLIAMSBURG, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $350,000–1 million | THE CHEESE SHOP OF VIRGINIA, INC. | WILLIAMSBURG, VA | Towne Bank |
| $150,000–350,000 | THE COLONIAL GROUP | WILLIAMSBURG, VA | Atlantic Union Bank |
| $150,000–350,000 | THE KENSINGTON SCHOOL, LLC | WILLIAMSBURG, VA | The Old Point National Bank of Phoebus |
| $150,000–350,000 | THE WILLIAMSBURG DENTAL GROUP, PLC | WILLIAMSBURG, VA | Towne Bank |
| $350,000–1 million | THE WILLIAMSBURG WINERY LTD | WILLIAMSBURG, VA | Atlantic Union Bank |
| $350,000–1 million | TIMOTHY K. JOHNSTON DDS & ASSOCIATES PLLC | WILLIAMSBURG, VA | The Old Point National Bank of Phoebus |
| $150,000–350,000 | TRELLIS VENTURE LLC | WILLIAMSBURG, VA | Chesapeake Bank |
| $350,000–1 million | TWO RIVERS CLUB AT THE GOVERNOR | WILLIAMSBURG, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $2–5 million | VELOCITY URGENT CARE LLC | WILLIAMSBURG, VA | Illinois Bank & Trust |
| $150,000–350,000 | VICK COMPANIES, INC. | WILLIAMSBURG, VA | The Old Point National Bank of Phoebus |
| $1–2 million | VIRGINIA UNITED METHODIST HOME OF WILLIAMSBURG INC | WILLIAMSBURG, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | VM & SONS INC | WILLIAMSBURG, VA | Chesapeake Bank |
| $350,000–1 million | W. H. H. TRICE & CO | WILLIAMSBURG, VA | Chesapeake Bank |
| $350,000–1 million | WALSINGHAM ACADEMY | WILLIAMSBURG, VA | Towne Bank |
| $150,000–350,000 | WAYNE HARBIN BUILDER, INC. | WILLIAMSBURG, VA | Citizens and Farmers Bank |
| $350,000–1 million | WILLIAMBURG MOTOR CARS INC | WILLIAMSBURG, VA | Towne Bank |
| $350,000–1 million | WILLIAMS LANDSCAPE AND DESIGN, INC | WILLIAMSBURG, VA | Chesapeake Bank |
| $150,000–350,000 | WILLIAMSBURG ALEWERKS LLC | WILLIAMSBURG, VA | Chesapeake Bank |
| $150,000–350,000 | WILLIAMSBURG AREA MEDICAL ASSISTANCE CORPORATION | WILLIAMSBURG, VA | Towne Bank |
| $350,000–1 million | WILLIAMSBURG AUTOS INC. | WILLIAMSBURG, VA | Virginia National Bank |
| $150,000–350,000 | WILLIAMSBURG CHRISTIAN ACADEMY | WILLIAMSBURG, VA | Towne Bank |
| $150,000–350,000 | WILLIAMSBURG DRUG COMPANY, INCORPORATED | WILLIAMSBURG, VA | Live Oak Banking Company |
| $350,000–1 million | WILLIAMSBURG EMERGENCY PHYSICIANS, INC. | WILLIAMSBURG, VA | Towne Bank |
| $150,000–350,000 | WILLIAMSBURG FAMILY DENTISTRY, PC | WILLIAMSBURG, VA | Towne Bank |
| $150,000–350,000 | WILLIAMSBURG HERTITAGE FURNITURE CO. INC | WILLIAMSBURG, VA | The Old Point National Bank of Phoebus |
| $350,000–1 million | WILLIAMSBURG INDOOR SPORTS COMPLEX LLC | WILLIAMSBURG, VA | Citizens and Farmers Bank |
| $2–5 million | WILLIAMSBURG LANDING INC. | WILLIAMSBURG, VA | Manufacturers and Traders Trust Company |
| $150,000–350,000 | WILLIAMSBURG MERCHANTS INC | WILLIAMSBURG, VA | Sonabank |
| $150,000–350,000 | WILLIAMSBURG MONTESSORI SCHOOL | WILLIAMSBURG, VA | Chesapeake Bank |
| $150,000–350,000 | WILLIAMSBURG ORTHODONTICS PLLC | WILLIAMSBURG, VA | Towne Bank |
| $350,000–1 million | WILLIAMSBURG OSTETRICS & GYNECOLOGY PC INC. | WILLIAMSBURG, VA | Towne Bank |
| $150,000–350,000 | WILLIAMSBURG POTTERY FACTORY INC. | WILLIAMSBURG, VA | Village Bank |
| $150,000–350,000 | WILLIAMSBURG RETINA CENTER PLLC | WILLIAMSBURG, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | WILLIAMSBURG UNITED METHODIST CHRUCH | WILLIAMSBURG, VA | Towne Bank |
| $150,000–350,000 | WILLIAMSBURG-JAMES CITY COUNTY COMMUNITY ACTION AGENCY | WILLIAMSBURG, VA | Towne Bank |
| $150,000–350,000 | WMD JAMESTOWN MEMBER, LLC | WILLIAMSBURG, VA | Peoples National Bank, National Association |
| $150,000–350,000 | WNGGC OPS LLC | WILLIAMSBURG, VA | Citizens and Farmers Bank |