| Fairfield Indoor Tennis, Inc. | Arts, Entertainment, and Recreation | $180,049 | $181,289 | 24 | <$5M | AI Deep Dive |
| Sandas Cleaners, LLC | Other Services (except Public Administration) | $179,000 | $180,621 | 20 | <$5M | AI Deep Dive |
| Wings Unlimited Inc. | Administrative and Support and Waste Management | $176,767 | $178,016 | 7 | <$5M | AI Deep Dive |
| Wings Unlimited, Inc. | Professional, Scientific, and Technical Services | $176,767 | $177,866 | 9 | <$5M | AI Deep Dive |
| Quynhchi Vanlang Dmd & Eliot Essenfeld DDS | Health Care and Social Assistance | $174,918 | $176,192 | 9 | <$5M | AI Deep Dive |
| Quynchi Vanlang Dmd & Eliot Essenfeld Dds, PC | Health Care and Social Assistance | $174,900 | $176,596 | 9 | <$5M | AI Deep Dive |
| Sanda's Cleaners LLC | Other Services (except Public Administration) | $172,565 | $174,258 | 16 | <$5M | AI Deep Dive |
| Aesthetic Surgery Center LLC DBA Darien Medical Arts, Llc. | Health Care and Social Assistance | $171,910 | $174,432 | 20 | $6.3M | AI Deep Dive |
| St. John's R.c. Church Corporation | Other Services (except Public Administration) | $169,100 | $170,819 | 22 | N/A | AI Deep Dive |
| St. John's R.c. Church Corp. | Other Services (except Public Administration) | $169,100 | $170,406 | 21 | N/A | AI Deep Dive |
| Giovanni's II INC | Accommodation and Food Services | $168,800 | $169,799 | 8 | <$5M | AI Deep Dive |
| Dental Specialists of Darien LLP | Health Care and Social Assistance | $168,559 | $170,314 | 13 | <$5M | AI Deep Dive |
| Dental Specialists of Darien, LLP | Manufacturing | $168,500 | $170,407 | 12 | <$5M | AI Deep Dive |
| Saint Thomas More Roman Catholic Church Corporation, the | Other Services (except Public Administration) | $165,600 | $167,179 | 44 | N/A | AI Deep Dive |
| Butler Tibbetts LLC | Professional, Scientific, and Technical Services | $164,135 | $165,192 | 10 | <$5M | AI Deep Dive |
| Graberroberts, LLC | Professional, Scientific, and Technical Services | $162,200 | $165,035 | 6 | <$5M | AI Deep Dive |
| Fiona LLC | Accommodation and Food Services | $161,914 | $162,770 | 21 | <$5M | AI Deep Dive |
| Fairfield Fondue Inc. | Accommodation and Food Services | $160,169 | $161,604 | 21 | <$5M | AI Deep Dive |
| Butler Tibbetts, LLC | Professional, Scientific, and Technical Services | $157,880 | $159,186 | 10 | <$5M | AI Deep Dive |
| First Congregational Church Nursery | Health Care and Social Assistance | $157,272 | $157,763 | 26 | N/A | AI Deep Dive |
| First Congregational Church Nursery | Health Care and Social Assistance | $157,272 | $158,629 | 26 | N/A | AI Deep Dive |
| Douglas Vanderhorn Architects | Professional, Scientific, and Technical Services | $157,227 | $158,614 | 11 | <$5M | AI Deep Dive |
| Darien Pediatric Associates, LLC | Health Care and Social Assistance | $150,800 | $152,535 | 13 | <$5M | AI Deep Dive |
| Dental Arts of Darien PC | Health Care and Social Assistance | $150,000 | $151,307 | 9 | <$5M | AI Deep Dive |
| Darien Pediatric Associates LLC | Health Care and Social Assistance | $149,200 | $150,275 | 12 | <$5M | AI Deep Dive |