| R. Stone Co., LLC | Construction | $342,500 | $344,479 | 37 | $13.9M |  AI Deep Dive |
| Advanced Cardiovascular Specialists | Health Care and Social Assistance | $341,350 | $344,642 | 27 | $8.5M | AI Deep Dive |
| Steelpointe Restaurant Group, LLC | Finance and Insurance | $337,500 | $341,974 | 35 | $18.0M | AI Deep Dive |
| Congregation B'nai Israel | Other Services (except Public Administration) | $336,535 | $339,246 | 55 | N/A | AI Deep Dive |
| Bridgeport Chemists INC | Retail Trade | $335,100 | $337,836 | 45 | $7.9M | AI Deep Dive |
| Capital Preparatory Schools Incorporated | Educational Services | $334,789 | $337,953 | 16 | N/A | AI Deep Dive |
| White Rose Home Healthcare Agency LLC | Health Care and Social Assistance | $333,335 | $337,563 | 226 | $38.7M | AI Deep Dive |
| Bridgeport Rescue Mission INC | Other Services (except Public Administration) | $332,800 | $335,225 | 54 | $10.3M | AI Deep Dive |
| Pink & Pretty LLC | Retail Trade | $331,110 | $334,899 | 16 | $5.4M | AI Deep Dive |
| Precious Memories Child Care Center, Llc. | Health Care and Social Assistance | $329,746 | $331,887 | 48 | $7.8M | AI Deep Dive |
| Habitat for Humanity of Coastal Fairfield County, Inc. | Other Services (except Public Administration) | $319,245 | $322,260 | 26 | <$5M | AI Deep Dive |
| Habitat for Humanity of Coastal Fairfield County | Health Care and Social Assistance | $319,245 | $321,462 | 25 | <$5M | AI Deep Dive |
| Yonkers 4199 LLC | Accommodation and Food Services | $316,800 | $319,673 | 70 | $12.4M | AI Deep Dive |
| Ralph N Richs INC | Accommodation and Food Services | $310,200 | $314,067 | 50 | $8.9M | AI Deep Dive |
| Stockman O'connor Connors Pllc | Professional, Scientific, and Technical Services | $308,142 | $310,059 | 16 | <$5M | AI Deep Dive |
| The Globe Equipment Company | Wholesale Trade | $307,251 | $308,774 | 23 | $7.0M | AI Deep Dive |
| Mercy Learning Center of Bridgeport, INC | Educational Services | $305,208 | $307,294 | 41 | N/A | AI Deep Dive |
| Abc Sign Corporation | Manufacturing | $300,000 | $302,137 | 21 | $5.9M | AI Deep Dive |
| Abc Sign Corporation | Manufacturing | $300,000 | $303,222 | 20 | $5.6M | AI Deep Dive |
| L.p. Macadams Company INC | Manufacturing | $295,400 | $298,014 | 30 | $29.8M | AI Deep Dive |
| Pascale Communications, LLC | Professional, Scientific, and Technical Services | $289,860 | $292,551 | 20 | <$5M | AI Deep Dive |
| Lindade Construction INC | Construction | $288,450 | $291,248 | 16 | <$5M | AI Deep Dive |
| A Dicesare Associates PC | Professional, Scientific, and Technical Services | $286,420 | $288,892 | 17 | <$5M | AI Deep Dive |
| Lindade Construction Inc. | Construction | $285,946 | $289,581 | 15 | <$5M | AI Deep Dive |
| Building Maintenance Enterprises | Administrative and Support and Waste Management | $282,000 | $284,588 | 41 | $8.9M | AI Deep Dive |