| $150,000–350,000 | RONALD W. ATWOOD, MD, PC | CHESAPEAKE, VA | Southern Bank and Trust Company |
| $1–2 million | RRMM ARCHITECTS, P.C. | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | RRMM DESIGN BUILD, LLC | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | RUSSELL'S HEATING AND AIR CONDITIONING, INC. | CHESAPEAKE, VA | Southern Bank and Trust Company |
| $150,000–350,000 | RYAN BOYLAN DDS PC | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | S M MASONRY AND STONE, LLC | CHESAPEAKE, VA | Dollar Bank, A Federal Savings Bank |
| $150,000–350,000 | SAK DEVELOPERS LLC | CHESAPEAKE, VA | Atlantic Union Bank |
| $350,000–1 million | SECURED NETWORK SOLUTIONS, INC. | CHESAPEAKE, VA | Touchstone Bank |
| $350,000–1 million | SERENITY HOME HEALTH CARE | CHESAPEAKE, VA | Wells Fargo Bank, National Association |
| $2–5 million | SERVICE TRANSFER, INC. | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | SIMMONS HEATING & COOLING INC | CHESAPEAKE, VA | Truist Bank |
| $150,000–350,000 | SITE IMPROVEMENT ASSOCIATES, INC. | CHESAPEAKE, VA | The Old Point National Bank of Phoebus |
| $2–5 million | SMITH & KEENE ELECTRIC SERVICE INC | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | SOUTH BAY COMMUNICATIONS INC. | CHESAPEAKE, VA | Atlantic Union Bank |
| $150,000–350,000 | SOUTH NORFOLK TRUCKING | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | SOUTHEASTERN MECHANICAL, INC. | CHESAPEAKE, VA | Southern Bank and Trust Company |
| $150,000–350,000 | SOUTHERN PACKING CORPORATION | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | SOUTHSIDE EYE CARE, PLLC | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | SOUTHSIDE FOOD SOLUTIONS, LLC | CHESAPEAKE, VA | TowneBank |
| $1–2 million | SPORTS MEDICINE AND ORTHOPAEDIC CENTER INC | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | SPRINKLE MASONRY INCORPORATED | CHESAPEAKE, VA | Atlantic Union Bank |
| $1–2 million | STANDARD CALIBRATIONS, INC | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | STARTLING GUTTERING AND ASSOCIATES OF SOUTHSIDE, INC. | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | STEPHEN ALEXANDER HOMES, LLC | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | STEVE DOLL TEAM LLC | CHESAPEAKE, VA | ABNB FCU |
| $150,000–350,000 | STILWELL & ASSOCIATES OF THE USA | CHESAPEAKE, VA | Truist Bank |
| $350,000–1 million | STONEBRIDGE SCHOOL | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | SUPERIOR EQUIPMENT SALES, INC | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | SYNERGY HEALTH SYSTEMS LLC | CHESAPEAKE, VA | Wells Fargo Bank, National Association |
| $2–5 million | TALLAHASSEE AUTOMOTIVE, LLC | CHESAPEAKE, VA | Atlantic Union Bank |
| $350,000–1 million | TAYLOR ENTERPRISES OF VA LLC | CHESAPEAKE, VA | Truist Bank |
| $150,000–350,000 | TAYLOR MADE DIAGNOSTICS, INC. | CHESAPEAKE, VA | Southern Bank and Trust Company |
| $150,000–350,000 | TEB CHES INC | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | TEB SUF INC | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | TEB VB INC | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | TECHCOMP, INC | CHESAPEAKE, VA | Atlantic Union Bank |
| $5–10 million | TECNICO CORPORATION | CHESAPEAKE, VA | Truist Bank |
| $150,000–350,000 | THE BUTCHER'S SON INC | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | THE DAVISHAR GROUP, INC. | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | THE GOVCON GROUP LLC | CHESAPEAKE, VA | TowneBank |
| $1–2 million | THE MCHENRY MANAGEMENT GROUP | CHESAPEAKE, VA | Truist Bank |
| $150,000–350,000 | THE REAL ESTATE GROUP LLC | CHESAPEAKE, VA | Blue Ridge Bank, National Association |
| $150,000–350,000 | THE TOWNSEND COMPANIES INC | CHESAPEAKE, VA | Truist Bank |
| $150,000–350,000 | THE WILD WING CANTINA INC | CHESAPEAKE, VA | Atlantic Union Bank |
| $150,000–350,000 | TIDEWATER AUTO PAINTING, INC. | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | TIDEWATER EMERGENCY MEDICAL CARE LTD | CHESAPEAKE, VA | TowneBank |
| $2–5 million | TIDEWATER FIBRE CORP | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | TIDEWATER GASTROENTEROLOGY PLLC | CHESAPEAKE, VA | Truist Bank |
| $350,000–1 million | TIDEWATER HEALTHCARE SERVICES, INC | CHESAPEAKE, VA | Blue Ridge Bank, National Association |
| $350,000–1 million | TIDEWATER HOME FUNDING, LLC | CHESAPEAKE, VA | Atlantic Union Bank |
| $350,000–1 million | TIDEWATER INTERIOR WALL AND CEILING, INC. | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | TIDEWATER LANDWORKS, INC. | CHESAPEAKE, VA | Atlantic Union Bank |
| $350,000–1 million | TIPS EAST LLC | CHESAPEAKE, VA | FirstBank |
| $150,000–350,000 | TITAN TALENT DEVELOPMENT LLC | CHESAPEAKE, VA | PNC Bank, National Association |
| $150,000–350,000 | TITLEQUEST OF HAMPTON ROADS, LLC | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | TRADE TEAM USA, LLC | CHESAPEAKE, VA | TowneBank |
| $2–5 million | TRADE TEAM, LLC | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | TRI-STAR ELECTRIC, INC. | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | TRINITY SALON INC | CHESAPEAKE, VA | Bank of America, National Association |
| $150,000–350,000 | TSO ARMOR AND TRAINING INC. | CHESAPEAKE, VA | Truist Bank |
| $350,000–1 million | VANWIN COATINGS OF VA, LLC | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | VENUWORKS OF CHESAPEAKE, L.L.C. | CHESAPEAKE, VA | Availa Bank |
| $1–2 million | VICO CONSTRUCTION CORPORATION | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | VIRGINIA EQUIPMENT RENTAL, INC | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | VIRGINIA FLOORCRAFTERS, INC. | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | VIRGINIA LANDSCAPE MANAGEMENT INC | CHESAPEAKE, VA | Wells Fargo Bank, National Association |
| $150,000–350,000 | VIRGINIA NEUROLOGY AND SLEEP CENTER | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | VIRGINIA RV SOLUTIONS, INC. | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | VIRGINIA TRAILER SERVICES INC | CHESAPEAKE, VA | Bank of America, National Association |
| $150,000–350,000 | W. TODD BIVINS DDS MS PC | CHESAPEAKE, VA | Truist Bank |
| $150,000–350,000 | WATERWAY PLUMBING INC | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | WB&E CONSTRUCTION, INC. | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | WEATHER MAKERS, INC. | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | WEB TEKS, INC. | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | WEST SERVICE CENTER, INC. | CHESAPEAKE, VA | TowneBank |
| $150,000–350,000 | WESTVIEW FINANCIAL SERVICES VA LLC | CHESAPEAKE, VA | Atlantic Union Bank |
| $350,000–1 million | WHITE'S NURSERY AND GREENHOUSES, INC. | CHESAPEAKE, VA | Celtic Bank Corporation |
| $150,000–350,000 | WHOOPING CRANE, INC. | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | WINKE ORTHOPEDIC PAIN MANAGEMENT CENTER PLC | CHESAPEAKE, VA | TowneBank |
| $350,000–1 million | ZERO POINT INC. | CHESAPEAKE, VA | TowneBank |