| Buckley Maschoff & Talwalkar LLC | Professional, Scientific, and Technical Services | $387,105 | $389,491 | 11 | <$5M | Research |
| Ppx Hospitality Group LLC | Accommodation and Food Services | $382,456 | $385,746 | 34 | $6.0M | Research |
| Jones Roger Sherman Inn Inc. | Accommodation and Food Services | $379,500 | $384,687 | 41 | $7.3M | Research |
| Fellowship of Christians in Universities | Other Services (except Public Administration) | $370,000 | $372,737 | 42 | N/A | Research |
| Sywal Corporation | Accommodation and Food Services | $368,424 | $370,816 | 35 | $10.9M | Research |
| New England Pediatrics, LLP | Health Care and Social Assistance | $362,105 | $365,273 | 23 | $7.2M | Research |
| New England Pediatrics LLP | Health Care and Social Assistance | $361,890 | $364,022 | 15 | <$5M | Research |
| Ramze Zakka INC | Accommodation and Food Services | $352,143 | $354,478 | 35 | $6.2M | Research |
| Elm Partners LLC | Accommodation and Food Services | $343,494 | $346,289 | 34 | $6.0M | Research |
| New Canaan Library Inc. | Information | $340,500 | $342,808 | 39 | N/A | Research |
| Buckley Maschoff & Talwalkar LLC | Professional, Scientific, and Technical Services | $338,420 | $340,497 | 17 | <$5M | Research |
| Jm Lummis Company | Finance and Insurance | $318,868 | $321,934 | 10 | $5.1M | Research |
| St Marks Episcopal Church | Other Services (except Public Administration) | $312,200 | $313,752 | 15 | N/A | Research |
| Spiga New Canaan Group INC | Accommodation and Food Services | $309,200 | $312,412 | 4 | <$5M | Research |
| Hutchinson Tree Care Specialists INC | Administrative and Support and Waste Management | $297,307 | $299,824 | 22 | <$5M | Research |
| Elise Landscapes & Nursery, LLC | Administrative and Support and Waste Management | $296,025 | $299,204 | 10 | <$5M | Research |
| Gates in New Canaan LLC | Accommodation and Food Services | $290,339 | $293,871 | 30 | $5.3M | Research |
| Sywal Corporation | Arts, Entertainment, and Recreation | $287,680 | $289,784 | 35 | <$5M | Research |
| St. Mark's Episcopal Church | Other Services (except Public Administration) | $285,860 | $287,480 | 28 | N/A | Research |
| Tequila Mockingbird in New Canaan LLC | Accommodation and Food Services | $283,000 | $285,406 | 12 | <$5M | Research |
| Robidoux Landscaping, Inc. | Administrative and Support and Waste Management | $276,355 | $278,831 | 30 | $6.5M | Research |
| Ppx Hospitality Group LLC | Accommodation and Food Services | $273,100 | $276,301 | 34 | $6.0M | Research |
| Wadia Associates, LLC | Professional, Scientific, and Technical Services | $272,900 | $274,306 | 14 | <$5M | Research |
| Jones Roger Sherman Inn, Inc. | Accommodation and Food Services | $271,100 | $274,752 | 35 | $6.2M | Research |
| B E K Ventures INC DBA the Ups Store | Unknown | $262,740 | $265,365 | 34 | N/A | Research |