| Rank | Land Area ▼ | School District / Population |
| 1. | 263.00 sq mi | Regional High School District 01 / 15,412 |
| 2. | 150.14 sq mi | Regional High School District 07 / 13,739 |
| 3. | 116.65 sq mi | Regional High School District 19 / 36,619 |
| 4. | 87.29 sq mi | Regional School District 06 / 6,635 |
| 5. | 80.77 sq mi | Regional School District 12 / 7,549 |
| 6. | 79.27 sq mi | Regional School District 17 / 14,872 |
| 7. | 75.74 sq mi | Regional High School District 08 / 19,236 |
| 8. | 63.15 sq mi | Regional High School District 11 / 5,877 |
| 9. | 61.57 sq mi | New Milford School District / 27,821 |
| 10. | 60.65 sq mi | Woodstock School District / 7,916 |
| 11. | 60.53 sq mi | Regional School District 10 / 15,035 |
| 12. | 58.92 sq mi | Regional High School District 09 / 16,860 |
| 13. | 58.77 sq mi | Sharon School District / 2,746 |
| 14. | 58.04 sq mi | Stafford School District / 12,013 |
| 15. | 57.66 sq mi | Newtown School District / 27,960 |
| 16. | 57.24 sq mi | Salisbury School District / 3,708 |
| 17. | 57.12 sq mi | Regional High School District 05 / 28,462 |
| 18. | 56.74 sq mi | Regional School District 15 / 27,451 |
| 19. | 56.10 sq mi | Litchfield School District / 8,365 |
| 20. | 55.77 sq mi | Regional School District 14 / 13,402 |
| 21. | 54.86 sq mi | Regional School District 18 / 9,954 |
| 22. | 54.25 sq mi | East Haddam School District / 9,142 |
| 23. | 54.25 sq mi | North Stonington School District / 5,293 |
| 24. | 54.10 sq mi | Lebanon School District / 7,314 |
| 25. | 51.27 sq mi | Glastonbury School District / 34,661 |
| 26. | 48.98 sq mi | Colchester School District / 16,143 |
| 27. | 48.55 sq mi | Kent School District / 2,951 |
| 28. | 48.31 sq mi | Killingly School District / 17,281 |
| 29. | 47.62 sq mi | Greenwich School District / 62,141 |
| 30. | 47.12 sq mi | Guilford School District / 22,405 |
| 31. | 46.90 sq mi | Thompson School District / 9,390 |
| 32. | 46.06 sq mi | Cornwall School District / 1,505 |
| 33. | 45.32 sq mi | Norfolk School District / 1,486 |
| 34. | 44.60 sq mi | Mansfield School District / 26,328 |
| 35. | 42.36 sq mi | Plainfield School District / 15,270 |
| 36. | 42.26 sq mi | Suffield School District / 15,764 |
| 37. | 41.95 sq mi | Montville School District / 19,649 |
| 38. | 41.89 sq mi | Danbury School District / 82,781 |
| 39. | 41.02 sq mi | Middletown School District / 47,424 |
| 40. | 40.68 sq mi | Granby School District / 11,310 |
| 41. | 40.33 sq mi | Pomfret School District / 4,216 |
| 42. | 39.97 sq mi | Regional High School District 04 / 15,477 |
| 43. | 39.94 sq mi | Canterbury School District / 5,110 |
| 44. | 39.75 sq mi | Torrington School District / 35,774 |
| 45. | 39.63 sq mi | Tolland School District / 14,971 |
| 46. | 39.04 sq mi | Wallingford School District / 45,154 |
| 47. | 38.96 sq mi | Voluntown School District / 2,602 |
| 48. | 38.76 sq mi | Ashford School District / 4,297 |
| 49. | 38.66 sq mi | Stonington School District / 18,539 |
| 50. | 38.22 sq mi | Ledyard School District / 15,090 |
| 51. | 37.64 sq mi | Stamford School District / 125,401 |
| 52. | 37.57 sq mi | Coventry School District / 12,434 |
| 53. | 37.04 sq mi | New Hartford School District / 6,910 |
| 54. | 36.94 sq mi | Hebron School District / 9,627 |
| 55. | 36.31 sq mi | Regional School District 13 / 11,797 |
| 56. | 36.25 sq mi | Barkhamsted School District / 3,749 |
| 57. | 36.15 sq mi | Madison School District / 18,284 |
| 58. | 35.91 sq mi | Southington School District / 43,509 |
| 59. | 35.65 sq mi | East Hampton School District / 12,936 |
| 60. | 34.71 sq mi | Griswold School District / 11,952 |
| 61. | 34.52 sq mi | Ridgefield School District / 25,025 |
| 62. | 34.06 sq mi | Ellington School District / 15,725 |
| 63. | 34.00 sq mi | East Lyme School District / 19,118 |
| 64. | 33.92 sq mi | Simsbury School District / 23,681 |
| 65. | 33.29 sq mi | Willington School District / 5,994 |
| 66. | 33.27 sq mi | Enfield School District / 44,713 |
| 67. | 33.08 sq mi | Hartland School District / 2,211 |
| 68. | 33.07 sq mi | Cheshire School District / 29,272 |
| 69. | 32.91 sq mi | Canaan School District / 1,240 |
| 70. | 32.77 sq mi | Waterford School District / 19,499 |
| 71. | 32.74 sq mi | Oxford School District / 12,831 |
| 72. | 32.65 sq mi | Hamden School District / 61,605 |
| 73. | 32.51 sq mi | Winchester School District / 11,089 |
| 74. | 31.53 sq mi | Colebrook School District / 1,594 |
| 75. | 31.50 sq mi | Redding School District / 9,267 |
| 76. | 31.03 sq mi | Groton School District / 40,136 |
| 77. | 30.82 sq mi | Preston School District / 4,735 |
| 78. | 30.63 sq mi | Shelton School District / 40,472 |
| 79. | 29.90 sq mi | Fairfield School District / 60,678 |
| 80. | 29.50 sq mi | Windsor School District / 29,130 |
| 81. | 29.09 sq mi | Brooklyn School District / 8,240 |
| 82. | 29.01 sq mi | Watertown School District / 22,286 |
| 83. | 28.92 sq mi | Eastford School District / 1,726 |
| 84. | 28.92 sq mi | Salem School District / 4,176 |
| 85. | 28.80 sq mi | Union School District / 950 |
| 86. | 28.52 sq mi | Waterbury School District / 109,887 |
| 87. | 28.37 sq mi | Somers School District / 11,431 |
| 88. | 28.06 sq mi | South Windsor School District / 25,795 |
| 89. | 28.06 sq mi | Norwich School District / 40,378 |
| 90. | 28.02 sq mi | Farmington School District / 25,515 |
| 91. | 27.42 sq mi | Easton School District / 7,593 |
| 92. | 27.40 sq mi | Manchester School District / 58,270 |
| 93. | 27.22 sq mi | Sterling School District / 3,809 |
| 94. | 26.97 sq mi | Windham School District / 25,271 |
| 95. | 26.80 sq mi | Wilton School District / 18,519 |
| 96. | 26.41 sq mi | Bristol School District / 60,556 |
| 97. | 26.32 sq mi | Berlin School District / 20,352 |
| 98. | 26.25 sq mi | East Windsor School District / 11,353 |
| 99. | 26.09 sq mi | Bloomfield School District / 20,626 |
| 100. | 26.07 sq mi | Monroe School District / 19,744 |
| 101. | 25.09 sq mi | Hampton School District / 1,912 |
| 102. | 24.76 sq mi | North Branford School District / 14,387 |
| 103. | 24.59 sq mi | Canton School District / 10,334 |
| 104. | 23.89 sq mi | Regional School District 16 / 15,680 |
| 105. | 23.79 sq mi | Meriden School District / 60,616 |
| 106. | 23.35 sq mi | Marlborough School District / 6,428 |
| 107. | 23.35 sq mi | Portland School District / 9,483 |
| 108. | 23.32 sq mi | Trumbull School District / 36,444 |
| 109. | 23.15 sq mi | Avon School District / 18,298 |
| 110. | 22.86 sq mi | Norwalk School District / 87,214 |
| 111. | 22.19 sq mi | New Canaan School District / 20,073 |
| 112. | 22.18 sq mi | Milford School District / 53,039 |
| 113. | 21.89 sq mi | Plymouth School District / 12,085 |
| 114. | 21.89 sq mi | Sherman School District / 3,636 |
| 115. | 21.84 sq mi | West Hartford School District / 63,396 |
| 116. | 21.83 sq mi | Branford School District / 28,066 |
| 117. | 21.37 sq mi | Columbia School District / 5,472 |
| 118. | 21.13 sq mi | Bethany School District / 5,546 |
| 119. | 20.84 sq mi | North Haven School District / 23,997 |
| 120. | 20.44 sq mi | New Fairfield School District / 14,079 |
| 121. | 20.43 sq mi | Wolcott School District / 16,724 |
| 122. | 20.30 sq mi | Putnam School District / 9,515 |
| 123. | 19.96 sq mi | Bozrah School District / 2,631 |
| 124. | 19.96 sq mi | Westport School District / 27,055 |
| 125. | 19.80 sq mi | Weston School District / 10,319 |
| 126. | 19.77 sq mi | Brookfield School District / 16,774 |
| 127. | 19.49 sq mi | Franklin School District / 1,993 |
| 128. | 19.47 sq mi | North Canaan School District / 3,262 |
| 129. | 19.43 sq mi | Chaplin School District / 2,256 |
| 130. | 18.81 sq mi | Woodbridge School District / 8,969 |
| 131. | 18.68 sq mi | New Haven School District / 130,553 |
| 132. | 18.63 sq mi | Scotland School District / 1,709 |
| 133. | 18.00 sq mi | East Hartford School District / 51,211 |
| 134. | 17.70 sq mi | Vernon School District / 29,162 |
| 135. | 17.56 sq mi | East Granby School District / 5,098 |
| 136. | 17.48 sq mi | Stratford School District / 52,092 |
| 137. | 17.38 sq mi | Hartford School District / 125,211 |
| 138. | 17.18 sq mi | Orange School District / 13,947 |
| 139. | 16.89 sq mi | Bethel School District / 19,078 |
| 140. | 16.31 sq mi | Naugatuck School District / 31,790 |
| 141. | 16.29 sq mi | Lisbon School District / 4,340 |
| 142. | 16.21 sq mi | Clinton School District / 13,188 |
| 143. | 16.05 sq mi | Chester School District / 4,223 |
| 144. | 15.97 sq mi | Bridgeport School District / 146,680 |
| 145. | 15.78 sq mi | Westbrook School District / 6,916 |
| 146. | 15.45 sq mi | Andover School District / 3,181 |
| 147. | 15.04 sq mi | Old Saybrook School District / 10,222 |
| 148. | 14.52 sq mi | Seymour School District / 16,551 |
| 149. | 14.41 sq mi | Bolton School District / 4,963 |
| 150. | 13.51 sq mi | Deep River School District / 4,611 |
| 151. | 13.45 sq mi | Rocky Hill School District / 19,838 |
| 152. | 13.39 sq mi | New Britain School District / 73,095 |
| 153. | 13.25 sq mi | Sprague School District / 2,993 |
| 154. | 13.14 sq mi | Newington School District / 30,652 |
| 155. | 12.66 sq mi | Darien School District / 21,190 |
| 156. | 12.45 sq mi | Cromwell School District / 14,077 |
| 157. | 12.31 sq mi | Wethersfield School District / 26,579 |
| 158. | 12.30 sq mi | East Haven School District / 29,139 |
| 159. | 11.97 sq mi | Thomaston School District / 7,793 |
| 160. | 10.75 sq mi | West Haven School District / 55,290 |
| 161. | 10.40 sq mi | Essex School District / 6,643 |
| 162. | 9.71 sq mi | Plainville School District / 17,791 |
| 163. | 9.02 sq mi | Windsor Locks School District / 12,554 |
| 164. | 6.02 sq mi | Ansonia School District / 19,128 |
| 165. | 5.62 sq mi | New London School District / 27,536 |
| 166. | 5.06 sq mi | Derby School District / 12,837 |
Please note that we only rank locations with 'Land Area' data. The rank above might not be a complete list. Locations without 'Land Area' data are not listed.
