| 1 | decco | €137.1M | 350 | 70 | B |
| 2 | BROOKLINE DENTAL CENTER | €38.1M | 30 | 60 | C+ |
| 3 | RHM International, LLC | €23.7M | 125 | 60 | C+ |
| 4 | Dharma Systems | €21.3M | 125 | 60 | C+ |
| 5 | The Arcadian Hotel Brookline | €20.5M | 125 | 60 | C+ |
| 6 | Courtyard by Marriott Boston Brookline | €20.5M | 125 | 60 | C+ |
| 7 | BodyScapes Fitness | €20.3M | 125 | 60 | C+ |
| 8 | Dexter Southfield School | €19.2M | 350 | 60 | C+ |
| 9 | bay state foods | €13.8M | -- | 60 | C+ |
| 10 | Boston Rug Company & Interiors | €12.2M | 30 | 60 | C+ |
| 11 | Channel Play Corporation | €12.2M | 30 | 60 | C+ |
| 12 | Eureka! Puzzles | €12.2M | 30 | 60 | C+ |
| 13 | Eugene Chernin Co | €12.2M | 30 | 60 | C+ |
| 14 | kupel’s bakery | €12.2M | 30 | 60 | C+ |
| 15 | Seguro De Vida Futuro | €11.0M | 30 | 60 | C+ |
| 16 | Preply | €10.6M | 350 | 60 | C+ |
| 17 | Hellenic College Holy Cross | €10.5M | 92 | 60 | C+ |
| 18 | Counterpoint Management Corporation | €8.2M | 125 | 50 | C |
| 19 | The Country Club - Brookline, MA | €8.0M | 350 | 50 | C |
| 20 | Eilat Cafe | €7.4M | 30 | 50 | C |
| 21 | All In Energy | €6.8M | 30 | 50 | C |
| 22 | Arbour Hri | €6.7M | 125 | 50 | C |
| 23 | BioCare Diagnostics, Inc. | €6.7M | 125 | 50 | C |
| 24 | Boston Laser - Boston Eye Group | €6.7M | 125 | 50 | C |
| 25 | Dynamic Capital Mortgage | €6.3M | 30 | 50 | C |
| 26 | IBP Institute | €6.3M | 30 | 50 | C |
| 27 | CATERING BY ANDREW, INC. | €6.0M | 30 | 50 | C |
| 28 | brookline ice & coal co., inc | €6.0M | 30 | 50 | C |
| 29 | brookline fine wine & gourmet | €6.0M | 30 | 50 | C |
| 30 | allium market & cafe | €6.0M | 30 | 50 | C |
| 31 | TireTutor | €5.9M | 30 | 50 | C |
| 32 | university road preschool | €5.7M | 30 | 50 | C |
| 33 | liner tire inc | €5.7M | 30 | 50 | C |
| 34 | little laurel pre school | €5.7M | 30 | 50 | C |
| 35 | Excalibur Electrical of Boston MA | €5.7M | 30 | 50 | C |
| 36 | Purchased. | €5.5M | 30 | 50 | C |
| 37 | Zaftigs | €5.1M | 125 | 50 | C |
| 38 | CardioLog Analytics | €5.1M | 30 | 50 | C |
| 39 | Shiman Associates | €5.1M | 30 | 50 | C |
| 40 | T6 Health Systems | €5.1M | 30 | 50 | C |
| 41 | studio elle pilates | €5.0M | 30 | 50 | C |
| 42 | leonard b. miller md pc | €5.0M | 30 | 50 | C |
| 43 | coolidge corner strength & fitness | €5.0M | 30 | 50 | C |
| 44 | boston kettlebell | €5.0M | 30 | 50 | C |
| 45 | performing arts occupational therapy | €5.0M | 30 | 50 | C |
| 46 | boston maternal-fetal medicine | €5.0M | 30 | 50 | C |
| 47 | village family chiropractic of brookline, ma | €5.0M | 30 | 50 | C |
| 48 | gary login, d.m.d., d.m.sc | €5.0M | 30 | 50 | C |
| 49 | rebecca caplan dc | €5.0M | 30 | 50 | C |
| 50 | Hilton Garden Inn Boston/Brookline | €4.9M | 30 | 50 | C |
| 51 | neil stone’s karate academy | €4.9M | 30 | 50 | C |
| 52 | ZVI Construction, LLC. | €4.5M | 30 | 50 | C |
| 53 | Facility Grid | €4.5M | 30 | 50 | C |
| 54 | Brian Tardif Construction | €4.5M | 30 | 50 | C |
| 55 | Rehkemper And Son INC | €4.5M | 30 | 50 | C |
| 56 | bienmoyo charitable foundation | €3.8M | 5 | 50 | C |
| 57 | algopan, inc | €3.5M | 125 | 50 | C |
| 58 | Datacom Telecommunications | €3.5M | 30 | 50 | C |
| 59 | Longwood Security Svc Inc | €3.5M | 30 | 50 | C |
| 60 | Boston University African American & Black Diaspora Studies Program | €3.4M | 30 | 50 | C |
| 61 | wow summer school | €3.4M | 30 | 50 | C |
| 62 | OnlineJewishLearning.com | €3.4M | 30 | 50 | C |
| 63 | childrens center of brookline & greater boston inc | €3.4M | 30 | 50 | C |
| 64 | The Public Library of Brookline Coolidge Corner Branch | €3.0M | 30 | 50 | C |
| 65 | Town of Brookline (MA) Council on Aging | €3.0M | 30 | 50 | C |
| 66 | Brookline Police Dept | €3.0M | 30 | 50 | C |
| 67 | audio studio sales | €2.9M | 30 | 50 | C |
| 68 | testpath, inc. | €2.9M | 30 | 50 | C |
| 69 | Dexter Southfield Summer Camps | €2.9M | 125 | 50 | C |
| 70 | myStockOptions.com | €2.8M | 30 | 50 | C |
| 71 | FASTHOCKEY, INC. | €2.8M | 30 | 50 | C |
| 72 | WangPC Computer Services | €2.8M | 30 | 50 | C |
| 73 | S9 Consulting | €2.8M | 30 | 50 | C |
| 74 | boston school of guitar | €2.8M | 30 | 50 | C |
| 75 | biana’s flowers | €2.8M | 30 | 50 | C |
| 76 | brookline auction gallery llc | €2.8M | 30 | 50 | C |
| 77 | antiquers iii | €2.8M | 30 | 50 | C |
| 78 | autrefois antiques | €2.8M | 30 | 50 | C |
| 79 | art alternative gallery | €2.8M | 30 | 50 | C |
| 80 | brocades | €2.8M | 30 | 50 | C |
| 81 | sing for joy | €2.8M | 30 | 50 | C |
| 82 | artana gallery | €2.8M | 30 | 50 | C |
| 83 | redress boston | €2.8M | 30 | 50 | C |
| 84 | albert’s of brookline | €2.8M | 30 | 50 | C |
| 85 | VIRB, INC. | €2.7M | 30 | 50 | C |
| 86 | Clear Flour Bread Bakery | €2.5M | 5 | 50 | C |
| 87 | languages exchange | €2.5M | 125 | 50 | C |
| 88 | Zaftigs Restaurant and Deli | €2.2M | 17 | 50 | C |
| 89 | Vintage Jewelry & Modern Boutique | €2.0M | 5 | 50 | C |
| 90 | Discovery Shop American Cancer | €2.0M | 5 | 50 | C |
| 91 | Israel Bookshop Inc | €2.0M | 5 | 50 | C |
| 92 | Audi Brookline, A Herb Chambers Company | €2.0M | 5 | 50 | C |
| 93 | Liner Tire Co | €2.0M | 5 | 50 | C |
| 94 | Aboutface Corp | €2.0M | 5 | 50 | C |
| 95 | Pantry. | €2.0M | 5 | 50 | C |
| 96 | UsTrendy, INC. | €2.0M | 5 | 50 | C |
| 97 | H.C.B. | €2.0M | 5 | 50 | C |
| 98 | Birch & Whelk Candle Company | €2.0M | 5 | 50 | C |
| 99 | Kolgian Oriental Rug Galleries | €2.0M | 5 | 50 | C |
| 100 | Curds & Co. LLC | €2.0M | 5 | 50 | C |