| $150,000–350,000 | THE PARK HOUSE ACADEMY | WINTER PARK, FL | Truist Bank d/b/a Branch Banking & Trust Co |
| $350,000–1 million | THE PLUMMER PAINTING COMPANY | WINTER PARK, FL | Sunrise Bank |
| $1–2 million | THE TOLLIVER GROUP, INC. | WINTER PARK, FL | South State Bank, National Association |
| $2–5 million | THE WINTER PARK METHODIST CHURCH, INCORPORATED | WINTER PARK, FL | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | THUNDER ROAD MANAGEMENT GROUP, INC. | WINTER PARK, FL | South State Bank, National Association |
| $350,000–1 million | TOWER SYSTEMS SOUTH, INC. | WINTER PARK, FL | Great Western Bank |
| $150,000–350,000 | TRACTOR ENTERPRISES LLC | WINTER PARK, FL | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | TRAFFIC ENGINEERING AND MANAGEMENT LLC | WINTER PARK, FL | Pilot Bank |
| $150,000–350,000 | TRICOR INTERNATIONAL, LLC | WINTER PARK, FL | City National Bank of Florida |
| $350,000–1 million | TRILOMA FINANCIAL GROUP LLC | WINTER PARK, FL | Wells Fargo Bank, National Association |
| $1–2 million | TRINITY PREPARATORY SCHOOL OF FLORIDA | WINTER PARK, FL | Wells Fargo Bank, National Association |
| $150,000–350,000 | TRINITY ROOFING & CONSTRUCTION | WINTER PARK, FL | IBERIABANK |
| $150,000–350,000 | TSH OPERATIONS - GODFREY, LLC | WINTER PARK, FL | Cogent Bank |
| $150,000–350,000 | TSH OPERATIONS - GRANITE CITY, LLC | WINTER PARK, FL | Cogent Bank |
| $1–2 million | TUSCAN GARDENS MANAGEMENT CORPORATION | WINTER PARK, FL | KeyBank National Association |
| $350,000–1 million | UNIVERSITY DIAGNOSTIC INST WINTER PARK | WINTER PARK, FL | IBERIABANK |
| $150,000–350,000 | UNIVERSITY MEDICAL CARE, P.A. | WINTER PARK, FL | Seacoast National Bank |
| $150,000–350,000 | US HUMAN RESOURCES LLC | WINTER PARK, FL | Seacoast National Bank |
| $150,000–350,000 | USG DISTRIBUTION LLC | WINTER PARK, FL | Seaside National Bank & Trust |
| $350,000–1 million | VALINTRY SERVICES | WINTER PARK, FL | Cogent Bank |
| $150,000–350,000 | VESTAPOINT CAPITAL LLC | WINTER PARK, FL | First Republic Bank |
| $150,000–350,000 | VOTEY ENTERPRISES, LLC | WINTER PARK, FL | Seacoast National Bank |
| $1–2 million | WALKER & COMPANY CONSTRUCTION SERVICES INC | WINTER PARK, FL | Bank of America, National Association |
| $150,000–350,000 | WATER SOLUTIONS MARKETING LLC | WINTER PARK, FL | TD Bank, National Association |
| $150,000–350,000 | WHOLE FAMILY HEALTHCARE PA | WINTER PARK, FL | Regions Bank |
| $1–2 million | WINDERWEEDLE, HAINES, WARD & WOODMAN P.A. | WINTER PARK, FL | Regions Bank |
| $150,000–350,000 | WINTER PARK DAY NURSERY INC | WINTER PARK, FL | Valley National Bank |
| $150,000–350,000 | WINTER PARK HEALTH FOUNDATION INC. | WINTER PARK, FL | TD Bank, National Association |
| $2–5 million | WINTER PARK IMPORTS INC | WINTER PARK, FL | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | WINTER PARK LIBRARY ASSOCIATION, INC | WINTER PARK, FL | Winter Park National Bank |
| $150,000–350,000 | WINTER PARK PRESBYTERIAN CHURCH INC | WINTER PARK, FL | South State Bank, National Association |
| $150,000–350,000 | WORDWISE, INC. | WINTER PARK, FL | One Florida Bank |
| $150,000–350,000 | WPGC CONSTRUCTION LLC | WINTER PARK, FL | Seaside National Bank & Trust |
| $150,000–350,000 | X STUDIOS, INC. | WINTER PARK, FL | JPMorgan Chase Bank, National Association |
| $150,000–350,000 | YEILDING M.D., L.L.C. | WINTER PARK, FL | IBERIABANK |
| $350,000–1 million | ZIO GROUP, LLC | WINTER PARK, FL | Cogent Bank |