| 1 | David A. Bramble, Inc. | €52.9M | 350 | 60 | C+ |
| 2 | Chester River Landscaping, LLC | €52.9M | 350 | 60 | C+ |
| 3 | Tolchester Marina | €41.1M | 30 | 60 | C+ |
| 4 | Kent County Economic and Tourism Development | €35.2M | 350 | 60 | C+ |
| 5 | Gillespie Precast, LLC. | €18.9M | 125 | 60 | C+ |
| 6 | farmerswagon.org | €13.8M | -- | 60 | C+ |
| 7 | Production Sciences Inc | €6.9M | 30 | 50 | C |
| 8 | Marina Assist | €6.8M | 5 | 50 | C |
| 9 | Brown Advisory Student-Managed Investment Fund | €6.3M | 30 | 50 | C |
| 10 | The Chesapeake Bank & Trust Co. | €6.3M | 30 | 50 | C |
| 11 | old mill market & cafe | €6.0M | 30 | 50 | C |
| 12 | Chester River Wine & Cheese Co. | €6.0M | 30 | 50 | C |
| 13 | 98 cannon riverfront grille | €5.1M | 125 | 50 | C |
| 14 | university of maryland shore nursing and rehab | €5.0M | 30 | 50 | C |
| 15 | KRM Construction Company LLC | €4.5M | 30 | 50 | C |
| 16 | YERKES CONSTRUCTION CO., LLC | €4.5M | 30 | 50 | C |
| 17 | Gillespie & Son Inc | €4.5M | 30 | 50 | C |
| 18 | freds firearm service llc | €4.1M | 30 | 50 | C |
| 19 | chesapeake cnc manufacturing center | €4.1M | 30 | 50 | C |
| 20 | River City Upholstery & Sewing | €3.8M | 30 | 50 | C |
| 21 | Washington College Center for Environment & Society | €3.4M | 30 | 50 | C |
| 22 | Chestertown Police Dept | €3.0M | 30 | 50 | C |
| 23 | country beautiful | €2.8M | 30 | 50 | C |
| 24 | anthony’s flowers | €2.8M | 30 | 50 | C |
| 25 | BW Health Group | €2.7M | 125 | 50 | C |
| 26 | Washington College GIS Program | €2.7M | 30 | 50 | C |
| 27 | Ramsey GMC | €2.0M | 5 | 50 | C |
| 28 | Chestertown Lumber Co | €2.0M | 5 | 50 | C |
| 29 | Riverside Gas & Oil Co., Inc. | €2.0M | 5 | 50 | C |
| 30 | The Bookplate LLC | €2.0M | 5 | 50 | C |
| 31 | anita's cleaning corporation | €2.0M | 30 | 50 | C |
| 32 | KRM Development Corp. | €2.0M | 30 | 50 | C |
| 33 | Andy Andrews | €2.0M | 30 | 50 | C |
| 34 | Gallo Realty | €1.9M | 30 | 50 | C |
| 35 | Mid-Atlantic Facility Services, LLC | €1.9M | 30 | 50 | C |
| 36 | chestertown nursing + rehab | €1.6M | 125 | 50 | C |
| 37 | g matthews | €1.3M | 5 | 50 | C |
| 38 | the channel restaurant | €1.2M | 30 | 50 | C |
| 39 | LA Ruota Ristorante | €1.2M | 30 | 50 | C |
| 40 | crossfire cafe | €1.2M | 30 | 50 | C |
| 41 | luisa’s cucina italiana | €1.2M | 30 | 50 | C |
| 42 | procolino pizza & italian family restaurant | €1.2M | 30 | 50 | C |
| 43 | adirondack customs | €1.2M | 30 | 50 | C |
| 44 | Aerscher Diagnostics | €1.2M | 5 | 50 | C |
| 45 | simply bed & bread | €1.2M | 30 | 50 | C |
| 46 | Apw Wright Line | €1.2M | 5 | 50 | C |
| 47 | chester river yacht & country club of chestertown inc | €1.2M | 125 | 50 | C |
| 48 | Grieb Manufacturing Co | €1.2M | 5 | 50 | C |
| 49 | Kei Quality Resins | €1.1M | 5 | 50 | C |
| 50 | Elb Enterprises | €1.1M | 30 | 50 | C |
| 51 | THE SCHACHINGER GROUP, INC. | €1.1M | 30 | 50 | C |
| 52 | Chesapeake Architects Inc | €1.1M | 30 | 50 | C |
| 53 | Delmarva.io | €1.1M | 5 | 50 | C |
| 54 | Kent County Parole & Probation | €1.1M | 5 | 50 | C |
| 55 | Washington College Investment Society | €1.1M | 5 | 50 | C |
| 56 | COG Industries LLC | €1.0M | 5 | 40 | D |
| 57 | Black Eyed Susan Restaurant | €995K | 5 | 40 | D |
| 58 | tobriner consulting | €995K | 5 | 40 | D |
| 59 | Worton Creek Marina Inc | €987K | 5 | 40 | D |
| 60 | geno's automotive service | €951K | 5 | 40 | D |
| 61 | Deep Landing Workshop | €950K | 5 | 40 | D |
| 62 | Chestertown River Arts | €929K | 5 | 40 | D |
| 63 | JP Software | €851K | 5 | 40 | D |
| 64 | new yarmouth family practice | €834K | 5 | 40 | D |
| 65 | adv pain mgmt specialist, llc dba kure pain mgmt | €834K | 5 | 40 | D |
| 66 | Op Frederick's | €821K | 5 | 40 | D |
| 67 | Blue Heron Contracting | €755K | 5 | 40 | D |
| 68 | WARNER BROS CONSTRUCTION INC | €755K | 5 | 40 | D |
| 69 | Patrick G Jones Inc | €755K | 5 | 40 | D |
| 70 | lindsley builders llc | €755K | 5 | 40 | D |
| 71 | williams marine & cabinetry | €755K | 5 | 40 | D |
| 72 | chesapeake boat lift services, llc | €755K | 5 | 40 | D |
| 73 | UNIVERSITY OF MARYLAND SHORE REGIONAL HEALTH INC | €740K | 30 | 40 | D |
| 74 | the furniture silo | €638K | 5 | 40 | D |
| 75 | houston’s dockside emporium | €630K | 30 | 40 | D |
| 76 | c&c adirondack snowmobile tours | €630K | 30 | 40 | D |
| 77 | Austin Image | €627K | 5 | 40 | D |
| 78 | Peninsula Security Solutions | €576K | 5 | 40 | D |
| 79 | leapsoar coaching llc | €572K | 5 | 40 | D |
| 80 | Hickman House | €572K | 5 | 40 | D |
| 81 | Kent County Detention Ctr | €503K | 5 | 40 | D |
| 82 | Family & Community Partnerships of Kent County | €503K | 5 | 40 | D |
| 83 | Local Management Board | €503K | 5 | 40 | D |
| 84 | baldwin electrical co | €488K | 5 | 40 | D |
| 85 | brant lake taxi & transport service inc | €479K | 5 | 40 | D |
| 86 | Human Trafficking Search | €475K | 5 | 40 | D |
| 87 | BAON Enterprises, LLC | €473K | 5 | 40 | D |
| 88 | the treasures of travel | €465K | 5 | 40 | D |
| 89 | Ash Tree Talent & Advisory, LLC | €429K | 5 | 40 | D |
| 90 | service specialist | €429K | 5 | 40 | D |
| 91 | onyx vista | €353K | 5 | 40 | D |
| 92 | venn conferencing | €353K | 5 | 40 | D |
| 93 | it care & repair | €353K | 5 | 40 | D |
| 94 | Chesapeake Diesel | €340K | 5 | 40 | D |
| 95 | mays beauty shop | €340K | 5 | 40 | D |
| 96 | east coast storage llc | €328K | 5 | 40 | D |
| 97 | Grove Point REI | €328K | 5 | 40 | D |
| 98 | almost heaven realty | €328K | 5 | 40 | D |
| 99 | Doug Ashley Realtors | €328K | 5 | 40 | D |
| 100 | Cross Street Realtors LLC | €328K | 5 | 40 | D |