| $350,000–1 million | RITEWAY BUILDING SERVICES | WINTER PARK, FL | Seacoast National Bank |
| $150,000–350,000 | ROBERTS SUPPLY INC | WINTER PARK, FL | Bank of America, National Association |
| $350,000–1 million | ROGER HOLLER CHEVROLET CO | WINTER PARK, FL | Truist Bank |
| $1–2 million | ROLLINS COLLEGE | WINTER PARK, FL | Synovus Bank |
| $150,000–350,000 | RUGGIERO, MARTINEZ & NORTON, PA | WINTER PARK, FL | United Community Bank |
| $150,000–350,000 | RVR CONSULTING GROUP II LLC | WINTER PARK, FL | Truist Bank |
| $150,000–350,000 | RW2 MARKETING & DESIGN | WINTER PARK, FL | Truist Bank |
| $150,000–350,000 | SAFER HOME SERVICES, LLC | WINTER PARK, FL | First Bank of the Lake |
| $150,000–350,000 | SAN PEDRO CENTER | WINTER PARK, FL | Wells Fargo Bank, National Association |
| $2–5 million | SANDSPUR HOUSING PARTNERS, LTD | WINTER PARK, FL | United Community Bank |
| $350,000–1 million | SAVANNAH INVESTORS | WINTER PARK, FL | Truist Bank |
| $150,000–350,000 | SCEARCE, SATCHER & JUNG, P.A. | WINTER PARK, FL | Valley National Bank |
| $350,000–1 million | SELLATI & CO INC | WINTER PARK, FL | Wells Fargo Bank, National Association |
| $150,000–350,000 | SHARE THE CARE, INC. | WINTER PARK, FL | Truist Bank |
| $150,000–350,000 | SHEEGOG ON TOP CONTRACTING, LLC | WINTER PARK, FL | JPMorgan Chase Bank, National Association |
| $350,000–1 million | SIGHTHOUND, INC. | WINTER PARK, FL | United Community Bank |
| $150,000–350,000 | SIGNATURE LANDSCAPE CONTRACTORS LLC | WINTER PARK, FL | IberiaBank, A Division of First Horizon Bank |
| $150,000–350,000 | SKOLFIELD HOMES, LLC | WINTER PARK, FL | Newtek Small Business Finance, Inc. |
| $350,000–1 million | SLEETH ENTERPRISES LLC | WINTER PARK, FL | Truist Bank |
| $1–2 million | SM RESTAURANTS, INC | WINTER PARK, FL | Truist Bank |
| $150,000–350,000 | SOCO INTERIORS, INC. | WINTER PARK, FL | Seacoast National Bank |
| $350,000–1 million | SONOBI, INC | WINTER PARK, FL | Cogent Bank |
| $150,000–350,000 | SOUND STAGE INC | WINTER PARK, FL | Seacoast National Bank |
| $350,000–1 million | SPORTSCARE INSTITUTE, LLC | WINTER PARK, FL | JPMorgan Chase Bank, National Association |
| $1–2 million | ST. MARGARET MARY PARISH | WINTER PARK, FL | Seacoast National Bank |
| $350,000–1 million | STERLING MARKETING GROUP, LLC | WINTER PARK, FL | Valley National Bank |
| $150,000–350,000 | STONY POINT, INC. | WINTER PARK, FL | Seacoast National Bank |
| $150,000–350,000 | STS PETER AND PAUL CATHOLIC CHURCH | WINTER PARK, FL | Seacoast National Bank |
| $350,000–1 million | SUPERIOR ALUMINUM INSTALLATIONS, INC. | WINTER PARK, FL | Bank of America, National Association |
| $1–2 million | SUPERIOR MEDICAL STAFFING | WINTER PARK, FL | MidFirst Bank |
| $350,000–1 million | SURREY HOMES, LLC | WINTER PARK, FL | Seacoast National Bank |
| $350,000–1 million | T.V.S., INC. | WINTER PARK, FL | First Federal Bank |
| $150,000–350,000 | TASTE THE WINE HOSPITALITY GROUP, INC. | WINTER PARK, FL | Stearns Bank National Association |
| $150,000–350,000 | TASTE THE WINE, INC. | WINTER PARK, FL | Stearns Bank National Association |
| $350,000–1 million | TAXPREP2 LLC | WINTER PARK, FL | IberiaBank, A Division of First Horizon Bank |
| $150,000–350,000 | TEEMING VACATION RENTALS LLC | WINTER PARK, FL | Valley National Bank |
| $350,000–1 million | THE BALMORAL GROUP, LLC | WINTER PARK, FL | United Community Bank |
| $1–2 million | THE EAR, NOSE & THROAT SURGICAL ASSOCIATES, P.A. | WINTER PARK, FL | Seacoast National Bank |
| $1–2 million | THE GENEVA SCHOOL INC | WINTER PARK, FL | Fifth Third Bank |
| $150,000–350,000 | THE LEACH FIRM, P.A. | WINTER PARK, FL | JPMorgan Chase Bank, National Association |
| $2–5 million | THE MAYFLOWER RETIREMENT CENTER | WINTER PARK, FL | Berkshire Bank |
| $150,000–350,000 | THE ORLANDO AESTHETIC INSTITUTE, LLC | WINTER PARK, FL | Truist Bank |
| $350,000–1 million | THE PLUMMER PAINTING COMPANY | WINTER PARK, FL | Sunrise Bank |
| $1–2 million | THE TOLLIVER GROUP, INC. | WINTER PARK, FL | SouthState Bank, National Association |
| $2–5 million | THE WINTER PARK METHODIST CHURCH, INCORPORATED | WINTER PARK, FL | Truist Bank |
| $150,000–350,000 | THUNDER ROAD MANAGEMENT GROUP, INC. | WINTER PARK, FL | SouthState Bank, National Association |
| $150,000–350,000 | TILE SUPPLY INC | WINTER PARK, FL | Itria Ventures LLC |
| $350,000–1 million | TOWER SYSTEMS SOUTH, INC. | WINTER PARK, FL | First Interstate Bank |
| $150,000–350,000 | TRACTOR ENTERPRISES LLC | WINTER PARK, FL | Truist Bank |
| $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 | 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, A Division of First Horizon Bank |
| $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 | United Community Bank |
| $350,000–1 million | VALINTRY SERVICES | WINTER PARK, FL | Cogent Bank |
| $150,000–350,000 | VOTEY ENTERPRISES, LLC | WINTER PARK, FL | Seacoast National 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 |
| $150,000–350,000 | WINTER PARK PRESBYTERIAN CHURCH INC | WINTER PARK, FL | SouthState 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 | United Community Bank |
| $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, A Division of First Horizon Bank |
| $350,000–1 million | ZIO GROUP, LLC | WINTER PARK, FL | Cogent Bank |