| $150,000–350,000 | OAK GROVE MANOR SCHOOL, INC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | OCALLAGHAN CABLE SERVICES INC | CHESAPEAKE, VA | Wells Fargo Bank, National Association |
| $150,000–350,000 | OCEAN TUMBLERS, INC. | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | OFF THE HOOK SEAFOOD MARKET STEAMER & RAW BAR LLC | CHESAPEAKE, VA | Atlantic Union Bank |
| $150,000–350,000 | OIL EQUIPMENT SALES & SERVICE CO., INC | CHESAPEAKE, VA | ABNB FCU |
| $350,000–1 million | ONYX TECHNICAL SERVICES, INC | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $350,000–1 million | OPHTHALMIC CONSULTANTS OF TIDEWATER PC | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $350,000–1 million | ORGANIZATION MANAGEMENT GROUP | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | ORION ASSOCIATES, INC. | CHESAPEAKE, VA | Towne Bank |
| $2–5 million | OVM FINANCIAL, INC. | CHESAPEAKE, VA | Southern Bank and Trust Company |
| $150,000–350,000 | P G HARRIS CONSTRUCTION CO | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | PAINT BY TEACH, INC | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | PALLETT OIL, INC. | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | PARRISH-LAYNE DESIGN GROUP, LTD | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | PARROCO PRODUCTION GROUP INC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | PERFECT SOLUTIONS LLC | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $350,000–1 million | PETERS AND WHITE CONSTRUCTION COMPANY | CHESAPEAKE, VA | Wells Fargo Bank, National Association |
| $150,000–350,000 | PILLS & POWDER, LLC | CHESAPEAKE, VA | Fulton Bank, National Association |
| $350,000–1 million | PLAN BEE ACADAMY | CHESAPEAKE, VA | Farmers Bank |
| $150,000–350,000 | PLAZA AZTECA DOCK LANDING INC | CHESAPEAKE, VA | Readycap Lending, LLC |
| $150,000–350,000 | PLAZA AZTECA GAVIOTAS INC | CHESAPEAKE, VA | Readycap Lending, LLC |
| $150,000–350,000 | POINT HARBOR COMMUNITY CHURCH | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | PRECISE MACHINE & FABRICATION, INC. | CHESAPEAKE, VA | The Old Point National Bank of Phoebus |
| $1–2 million | PRECON MARINE, INC. | CHESAPEAKE, VA | The Old Point National Bank of Phoebus |
| $150,000–350,000 | PREMIER PLUMBING LLC | CHESAPEAKE, VA | Fulton Bank, National Association |
| $150,000–350,000 | PREMIER RESTORATIONS, LLC | CHESAPEAKE, VA | Fulton Bank, National Association |
| $350,000–1 million | PRIORITY AUTOMOTIVE CHESAPEAKE, INC. | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | PRIORITY GREENBRIER AUTOMOTIVE | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $1–2 million | PRIORITY IMPORTS BATTLEFIELD, INC. | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | PRIORITY IMPORTS GREENBRIER, INC. | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | PRIORITY STAFFING SERVICES, INC | CHESAPEAKE, VA | Towne Bank |
| $2–5 million | PRISM MARITIME, LLC | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | PROCREATE FERTILITY CENTER OF VIRGINIA PLLC | CHESAPEAKE, VA | PNC Bank, National Association |
| $350,000–1 million | PROFESSIONAL PRINTING CENTER, INC | CHESAPEAKE, VA | Southern Bank and Trust Company |
| $350,000–1 million | QUALITY COATINGS OF VIRGINIA, INC. | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | R&L MACHINE SHOP, INC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | R. A. STYRON HEATING AND AIR CONDITIONING, INC. | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | RADIOLOGY SERVICES OF NORTHERN VA, LLC | CHESAPEAKE, VA | The Old Point National Bank of Phoebus |
| $150,000–350,000 | RANCHO GRANDE INC | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | RB COMPREHENSIVE DENTISTRY | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | REACHING UNREACHED NATIONS, INC. | CHESAPEAKE, VA | Atlantic Union Bank |
| $150,000–350,000 | RECOVERY SPORTS GRILL CHESAPEAKE, LLC | CHESAPEAKE, VA | Chemung Canal Trust Company |
| $150,000–350,000 | REGION RENTS | CHESAPEAKE, VA | Atlantic Union Bank |
| $350,000–1 million | RELIANCE CONCRETE CONTRACTORS, INC | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | RENAISSANCE PEDIATRICS, PC | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | RENCON LLC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | RENEW SKIN & LASER CENTERS, LLC | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | RESCLEAN INC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | RESOURCE LIGHTING INC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | RETNAUER BAYNES ASSOCIATES, LLC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | REYNOLDS LANDSCAPING, INC. | CHESAPEAKE, VA | Atlantic Union Bank |
| $350,000–1 million | RIVER OAK CHURCH | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | ROBINSON TECHNOLOGIES INC | CHESAPEAKE, VA | Towne Bank |
| $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 | Towne Bank |
| $150,000–350,000 | RRMM DESIGN BUILD, LLC | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | RUSSELL'S HEATING AND AIR CONDITIONING, INC. | CHESAPEAKE, VA | Southern Bank and Trust Company |
| $150,000–350,000 | S M MASONRY AND STONE, LLC | CHESAPEAKE, VA | Dollar Bank, A Federal Savings Bank |
| $150,000–350,000 | SACRED ELEMENTS SPA INC. | CHESAPEAKE, VA | Atlantic Union 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 | Towne Bank |
| $150,000–350,000 | SIMMONS HEATING & COOLING INC | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $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 | Towne Bank |
| $350,000–1 million | SOUTH BAY COMMUNICATIONS INC. | CHESAPEAKE, VA | Atlantic Union Bank |
| $150,000–350,000 | SOUTH NORFOLK TRUCKING | CHESAPEAKE, VA | Farmers Bank |
| $350,000–1 million | SOUTHEASTERN MECHANICAL, INC. | CHESAPEAKE, VA | Southern Bank and Trust Company |
| $150,000–350,000 | SOUTHSIDE EYE CARE, PLLC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | SOUTHSIDE FOOD SOLUTIONS, LLC | CHESAPEAKE, VA | Towne Bank |
| $1–2 million | SPORTS MEDICINE AND ORTHOPAEDIC CENTER INC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | SPRING OAKS CAPITAL, LLC | CHESAPEAKE, VA | Univest Bank and Trust Co. |
| $350,000–1 million | SPRINKLE MASONRY INC. | CHESAPEAKE, VA | Atlantic Union Bank |
| $1–2 million | STANDARD CALIBRATIONS, INC | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | STARTLING GUTTERING AND ASSOCIATES OF SOUTHSIDE, INC. | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | STEPHEN ALEXANDER HOMES, LLC | CHESAPEAKE, VA | Towne Bank |
| $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 d/b/a Branch Banking & Trust Co |
| $350,000–1 million | STONEBRIDGE SCHOOL | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | SUB-STANTIAL CORP | CHESAPEAKE, VA | Fulton Bank, National Association |
| $350,000–1 million | SUPERIOR EQUIPMENT SALES, INC | CHESAPEAKE, VA | Towne Bank |
| $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 d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | TAYLOR MADE DIAGNOSTICS, INC. | CHESAPEAKE, VA | Southern Bank and Trust Company |
| $150,000–350,000 | TEB CHES INC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | TEB SUF INC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | TEB VB INC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | TECHCOMP, INC | CHESAPEAKE, VA | Atlantic Union Bank |
| $5–10 million | TECNICO CORPORATION | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | THE BATTERY SPECIALIST, INC | CHESAPEAKE, VA | Atlantic Union Bank |
| $150,000–350,000 | THE BUTCHER'S SON INC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | THE CHILLED PONDS LLC | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $350,000–1 million | THE DAVISHAR GROUP, INC. | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | THE GOVCON GROUP LLC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | THE LOOK INCORPORATED | CHESAPEAKE, VA | The Old Point National Bank of Phoebus |
| $1–2 million | THE MCHENRY MANAGEMENT GROUP | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | THE REAL ESTATE GROUP LLC | CHESAPEAKE, VA | Blue Ridge Bank, National Association |
| $150,000–350,000 | THE SILBAR GROUP CORP | CHESAPEAKE, VA | Navy FCU |