| 1 | Cranwell Spa & Golf Resort | €57.5M | 350 | 60 | C+ |
| 2 | Belvoir Terrace, Inc | €23.2M | 125 | 60 | C+ |
| 3 | Toole Companies | €20.5M | 125 | 60 | C+ |
| 4 | dallmeier surveillance systems | €18.0M | 350 | 60 | C+ |
| 5 | loeb’s foodtown | €13.8M | -- | 60 | C+ |
| 6 | Blauer Manufacturing | €12.2M | 30 | 60 | C+ |
| 7 | Ramsey's Market & Ramsey's Ace Hardware | €12.2M | 30 | 60 | C+ |
| 8 | Zogics Pet | €12.2M | 30 | 60 | C+ |
| 9 | Innovative Tooling Co | €9.4M | 30 | 50 | C |
| 10 | dalton ag, inc. | €6.8M | 30 | 50 | C |
| 11 | INTERNATIONAL BEVERAGE CENTER, INC. D/B/A/ NEJAIMES WINE & LIQUOR | €5.1M | 30 | 50 | C |
| 12 | kimball farms lifecare retirement community | €5.0M | 30 | 50 | C |
| 13 | Canyon Ranch In Lenox | €4.9M | 30 | 50 | C |
| 14 | Sandbox Pictures | €4.9M | 30 | 50 | C |
| 15 | World Paulownia Institute | €3.8M | 5 | 50 | C |
| 16 | Berkshire Information Systems | €3.5M | 30 | 50 | C |
| 17 | Lenox Police Dept | €3.0M | 30 | 50 | C |
| 18 | vip limousine service | €2.9M | 30 | 50 | C |
| 19 | N L C Inc | €2.8M | 30 | 50 | C |
| 20 | sienna gallery | €2.8M | 30 | 50 | C |
| 21 | Visit Lenox/LENOX CHAMBER OF COMMERCE | €2.0M | 5 | 50 | C |
| 22 | Shared Estates Fund | €2.0M | 30 | 50 | C |
| 23 | McCormack Builders | €2.0M | 5 | 50 | C |
| 24 | ESCO Energy Services Co. | €1.9M | 30 | 50 | C |
| 25 | New England Pain Ctr | €1.6M | 30 | 50 | C |
| 26 | Kimball Farms Nursing Ctr | €1.6M | 30 | 50 | C |
| 27 | Bulldog Transportation Inc. | €1.4M | 5 | 50 | C |
| 28 | lenox lumber co | €1.3M | 5 | 50 | C |
| 29 | halpins grub and grog | €1.2M | 30 | 50 | C |
| 30 | electra’s cafe | €1.2M | 30 | 50 | C |
| 31 | Prime Italian Steakhouse and Bar | €1.2M | 30 | 50 | C |
| 32 | Alta Restaurant & Wine Bar | €1.2M | 30 | 50 | C |
| 33 | Lenox Eats | €1.2M | 30 | 50 | C |
| 34 | sophia’s restaurant & pizza | €1.2M | 30 | 50 | C |
| 35 | lenox massage & bodywork | €1.2M | 30 | 50 | C |
| 36 | gateways inn & restaurant | €1.2M | 30 | 50 | C |
| 37 | amenie | €1.2M | 30 | 50 | C |
| 38 | courtyard by marriott lenox berkshires | €1.2M | 30 | 50 | C |
| 39 | Hughes Energy Tech llc | €1.1M | 5 | 50 | C |
| 40 | auction today estate resale & equipment auctions | €1.1M | 5 | 50 | C |
| 41 | peripheral mowers inc | €1.1M | 5 | 50 | C |
| 42 | ARC Investment Planning | €1.1M | 5 | 50 | C |
| 43 | kutsick enterprises llc | €951K | 5 | 40 | D |
| 44 | Richmond Autobody | €951K | 5 | 40 | D |
| 45 | Saftronics Inc | €950K | 5 | 40 | D |
| 46 | Gerry Brown | €851K | 5 | 40 | D |
| 47 | berkshire psychodynamic psychiatry inc | €834K | 5 | 40 | D |
| 48 | d & j home care 3, llc | €834K | 5 | 40 | D |
| 49 | jennifer valente | €834K | 5 | 40 | D |
| 50 | gary w. mcneely | €834K | 5 | 40 | D |
| 51 | LifeBreath with Lillian Lennox | €834K | 5 | 40 | D |
| 52 | Perfect Picnics | €821K | 5 | 40 | D |
| 53 | Whistler Inn | €821K | 5 | 40 | D |
| 54 | Garden Gables Inn | €821K | 5 | 40 | D |
| 55 | caligari sanitary supply | €818K | 5 | 40 | D |
| 56 | krofta technologies svc | €818K | 5 | 40 | D |
| 57 | Pro Glass & Aluminum | €755K | 5 | 40 | D |
| 58 | jc custom builders | €755K | 5 | 40 | D |
| 59 | Lenox Construction Co | €755K | 5 | 40 | D |
| 60 | SafeRx Pharma | €719K | 5 | 40 | D |
| 61 | Bedard Photo | €627K | 5 | 40 | D |
| 62 | Barb Shuttleworth | €627K | 5 | 40 | D |
| 63 | Taylor Ridge Estates Inc | €627K | 5 | 40 | D |
| 64 | Jo Ann Santangelo Visual Storyteller | €627K | 5 | 40 | D |
| 65 | Dalton Ag Products Inc | €612K | 5 | 40 | D |
| 66 | safe food works | €572K | 5 | 40 | D |
| 67 | huron pointe sportsmen’s assn | €556K | 30 | 40 | D |
| 68 | spears transport | €479K | 5 | 40 | D |
| 69 | tobi's limousine service inc | €479K | 5 | 40 | D |
| 70 | Krystal Services Ltd | €473K | 5 | 40 | D |
| 71 | the wit gallery of art & wine | €465K | 5 | 40 | D |
| 72 | executive talent solutions | €429K | 5 | 40 | D |
| 73 | webitronix | €353K | 5 | 40 | D |
| 74 | cls medical billing | €353K | 5 | 40 | D |
| 75 | Evergreen Home Real Estate | €328K | 5 | 40 | D |
| 76 | Cohen + White Associates LLC | €328K | 5 | 40 | D |
| 77 | berkshires homes real estate | €328K | 5 | 40 | D |
| 78 | Canyon Ranch Living Miami Bch | €328K | 5 | 40 | D |
| 79 | vytek usa | €316K | 30 | 40 | D |
| 80 | gorman capital strategies | €299K | 5 | 40 | D |
| 81 | innovation capital research | €283K | 5 | 40 | D |
| 82 | eastgate inn | €283K | 5 | 40 | D |
| 83 | carol wahler vocal studio | €280K | 30 | 40 | D |
| 84 | Lenox Care Ctr | €269K | 5 | 40 | D |
| 85 | Pierce Speech, Language, and Learning Center | €269K | 5 | 40 | D |
| 86 | PURSUIT OF INDEPENDENCE INC | €269K | 5 | 40 | D |
| 87 | Kimball Farms Lifecare | €269K | 5 | 40 | D |
| 88 | NUCARA PHARMACY #30 | €269K | 5 | 40 | D |
| 89 | lenox village integrative pharmacy | €265K | 30 | 40 | D |
| 90 | healthstar pharmacy inc. | €265K | 30 | 40 | D |
| 91 | Heller & Robbins PC | €253K | 5 | 40 | D |
| 92 | the little hot dog wagon | €204K | 5 | 40 | D |
| 93 | berkshire yogurt | €204K | 5 | 40 | D |
| 94 | my place donut & coffee shop | €204K | 5 | 40 | D |
| 95 | the ponds at fox hollow | €203K | 5 | 40 | D |
| 96 | pine acre bed & breakfast | €203K | 5 | 40 | D |
| 97 | hampton terrace bed and breakfast inn | €203K | 5 | 40 | D |
| 98 | apple tree inn & restaurant | €203K | 5 | 40 | D |
| 99 | keen william e cpa | €183K | 5 | 40 | D |
| 100 | Piretti Real Estate | €165K | 5 | 40 | D |