| Rank | Land Area ▼ | School District / Population |
| 1. | 210.38 sq mi | Central Berkshire School District / 13,907 |
| 2. | 203.01 sq mi | Gateway School District / 8,898 |
| 3. | 173.15 sq mi | Southern Berkshire School District / 7,188 |
| 4. | 171.95 sq mi | Mohawk Trail School District / 8,603 |
| 5. | 165.94 sq mi | Ralph C. Mahar School District / 11,057 |
| 6. | 165.60 sq mi | Quabbin School District / 15,772 |
| 7. | 150.92 sq mi | Wachusett School District / 42,131 |
| 8. | 129.05 sq mi | Hampshire School District / 12,499 |
| 9. | 115.54 sq mi | Tantasqua School District / 20,840 |
| 10. | 112.91 sq mi | Pioneer Valley School District / 6,549 |
| 11. | 104.44 sq mi | Frontier School District / 11,827 |
| 12. | 102.04 sq mi | Amherst-Pelham School District / 44,250 |
| 13. | 96.46 sq mi | Plymouth School District / 57,414 |
| 14. | 90.06 sq mi | Martha's Vineyard School District / 16,816 |
| 15. | 89.07 sq mi | Mount Greylock School District / 10,926 |
| 16. | 87.35 sq mi | Farmington River Regional School District / 2,366 |
| 16. | 87.35 sq mi | Lee/Berkshire Hills in Farmington River Regional (7-12) / 2,366 |
| 18. | 86.01 sq mi | Berkshire Hills School District / 10,505 |
| 19. | 79.10 sq mi | North Middlesex School District / 24,112 |
| 20. | 76.61 sq mi | New Salem-Wendell School District / 1,987 |
| 21. | 74.09 sq mi | Athol-Royalston School District / 12,847 |
| 22. | 73.80 sq mi | Ashburnham-Westminster School District / 13,494 |
| 23. | 70.77 sq mi | Nauset School District / 23,675 |
| 24. | 69.07 sq mi | Middleborough School District / 23,541 |
| 25. | 68.96 sq mi | Dighton-Rehoboth School District / 18,915 |
| 26. | 64.93 sq mi | Old Rochester School District / 16,421 |
| 27. | 64.73 sq mi | Nashoba School District / 19,886 |
| 28. | 64.03 sq mi | Freetown-Lakeville School District / 19,890 |
| 29. | 63.00 sq mi | Dudley-Charlton Regional School District / 24,759 |
| 30. | 62.38 sq mi | Southwick-Tolland School District / 11,686 |
| 31. | 60.92 sq mi | Dartmouth School District / 34,384 |
| 32. | 59.80 sq mi | Barnstable School District / 44,750 |
| 33. | 56.99 sq mi | Triton School District / 21,284 |
| 34. | 56.78 sq mi | Mohawk Trail Regional School District in Hawley and Charlemont towns / 1,653 |
| 34. | 56.78 sq mi | Hawlemont School District / 1,653 |
| 36. | 56.13 sq mi | Narragansett School District / 9,738 |
| 37. | 54.24 sq mi | Petersham School District / 1,277 |
| 38. | 52.64 sq mi | Belchertown School District / 14,774 |
| 39. | 49.84 sq mi | Westport School District / 15,647 |
| 40. | 49.70 sq mi | Adams-Cheshire School District / 11,593 |
| 41. | 49.41 sq mi | Up-Island Regional School District / 3,995 |
| 42. | 49.33 sq mi | Silver Lake School District / 23,315 |
| 43. | 49.22 sq mi | Groton-Dunstable School District / 14,296 |
| 44. | 48.93 sq mi | Masconomet School District / 23,664 |
| 45. | 48.28 sq mi | Boston School District / 639,594 |
| 46. | 48.16 sq mi | Chesterfield-Goshen School District / 2,372 |
| 47. | 48.03 sq mi | Quaboag Regional School District / 8,891 |
| 48. | 47.81 sq mi | Bridgewater-Raynham School District / 40,448 |
| 49. | 47.61 sq mi | King Philip School District / 31,279 |
| 50. | 46.76 sq mi | Williamstown School District / 7,624 |
| 51. | 46.70 sq mi | Taunton School District / 56,056 |
| 52. | 46.32 sq mi | Westfield School District / 41,371 |
| 53. | 44.97 sq mi | Nantucket School District / 10,414 |
| 54. | 44.80 sq mi | Lee School District / 6,340 |
| 55. | 44.66 sq mi | Dennis-Yarmouth School District / 37,793 |
| 56. | 44.14 sq mi | Monson School District / 8,660 |
| 57. | 44.07 sq mi | Falmouth School District / 31,576 |
| 58. | 43.92 sq mi | Gill-Montague School District / 9,967 |
| 59. | 43.02 sq mi | Winchendon School District / 10,466 |
| 60. | 42.74 sq mi | Sandwich School District / 20,605 |
| 61. | 42.68 sq mi | Spencer-East Brookfield School District / 14,009 |
| 62. | 42.31 sq mi | Lanesborough School District / 3,302 |
| 63. | 42.20 sq mi | Southwick-Tolland School District in Granville (9-12) / 1,566 |
| 63. | 42.20 sq mi | Granville School District / 1,566 |
| 65. | 41.80 sq mi | Hampden-Wilbraham School District / 19,537 |
| 66. | 40.64 sq mi | Bourne School District / 19,749 |
| 67. | 40.47 sq mi | Pittsfield School District / 44,226 |
| 68. | 39.78 sq mi | Concord-Carlisle School District / 23,801 |
| 69. | 39.34 sq mi | Mendon-Upton School District / 13,536 |
| 70. | 38.50 sq mi | Lincoln-Sudbury School District / 25,378 |
| 71. | 37.69 sq mi | Conway School District / 1,663 |
| 72. | 37.40 sq mi | Carver School District / 11,541 |
| 73. | 37.37 sq mi | Worcester School District / 182,511 |
| 74. | 37.22 sq mi | Sturbridge School District / 9,363 |
| 75. | 36.40 sq mi | Douglas School District / 8,578 |
| 76. | 35.86 sq mi | Wareham School District / 22,247 |
| 77. | 35.85 sq mi | Adams-Cheshire School District in Savoy (7-12) / 703 |
| 77. | 35.85 sq mi | Savoy School District / 703 |
| 79. | 35.67 sq mi | Mount Greylock/New Lebanon (NY) School Districts in Hancock (7-12) / 726 |
| 79. | 35.67 sq mi | Hancock School District / 726 |
| 81. | 35.09 sq mi | Orange School District / 7,793 |
| 82. | 35.05 sq mi | Florida School District / 906 |
| 83. | 34.74 sq mi | Brimfield School District / 3,667 |
| 84. | 34.47 sq mi | Freetown School District / 8,870 |
| 85. | 34.36 sq mi | Ware School District / 9,886 |
| 86. | 34.24 sq mi | Northampton School District / 28,637 |
| 87. | 33.58 sq mi | Rochester School District / 5,348 |
| 88. | 33.13 sq mi | Fall River School District / 88,756 |
| 89. | 32.97 sq mi | Haverhill School District / 61,769 |
| 90. | 32.50 sq mi | Northborough-Southborough School District / 24,513 |
| 91. | 32.41 sq mi | Sutton School District / 9,078 |
| 92. | 32.39 sq mi | Deerfield School District / 5,097 |
| 93. | 32.11 sq mi | Ipswich School District / 13,480 |
| 94. | 31.87 sq mi | Springfield School District / 153,836 |
| 95. | 31.58 sq mi | Palmer School District / 12,155 |
| 96. | 30.94 sq mi | Dover-Sherborn School District / 9,927 |
| 97. | 30.85 sq mi | Andover School District / 34,251 |
| 98. | 30.79 sq mi | Pentucket School District / 17,711 |
| 99. | 30.27 sq mi | Westford School District / 22,854 |
| 100. | 30.15 sq mi | Acton-Boxborough School District / 27,716 |
| 101. | 29.59 sq mi | Uxbridge School District / 13,609 |
| 102. | 29.56 sq mi | Lakeville School District / 10,602 |
| 103. | 29.03 sq mi | Berlin-Boylston School District / 7,316 |
| 104. | 28.81 sq mi | Leominster School District / 40,954 |
| 105. | 28.75 sq mi | Easton School District / 23,548 |
| 106. | 28.62 sq mi | Marshfield School District / 25,430 |
| 107. | 28.15 sq mi | Southampton School District / 5,958 |
| 108. | 27.83 sq mi | Granby School District / 6,301 |
| 109. | 27.83 sq mi | Fitchburg School District / 40,419 |
| 110. | 27.81 sq mi | Norton School District / 19,280 |
| 111. | 27.60 sq mi | Amherst School District / 39,260 |
| 112. | 27.20 sq mi | Ludlow School District / 21,288 |
| 113. | 27.17 sq mi | Westhampton School District / 1,586 |
| 114. | 26.81 sq mi | Attleboro School District / 43,774 |
| 115. | 26.81 sq mi | Edgartown School District / 4,186 |
| 116. | 26.63 sq mi | Franklin School District / 32,393 |
| 117. | 26.53 sq mi | Oxford School District / 13,772 |
| 118. | 26.52 sq mi | Shutesbury School District / 1,804 |
| 119. | 26.48 sq mi | Lunenburg School District / 10,797 |
| 120. | 26.44 sq mi | Harvard School District / 6,558 |
| 121. | 26.31 sq mi | North Andover School District / 28,963 |
| 122. | 26.26 sq mi | Hopkinton School District / 15,604 |
| 123. | 26.20 sq mi | Gloucester School District / 29,237 |
| 124. | 25.57 sq mi | Billerica School District / 41,446 |
| 125. | 25.56 sq mi | Williamsburg School District / 2,583 |
| 126. | 25.11 sq mi | Pelham School District / 1,350 |
| 127. | 25.04 sq mi | Framingham School District / 69,900 |
| 128. | 24.52 sq mi | Concord School District / 18,834 |
| 129. | 24.36 sq mi | North Adams School District in Florida (9-12) / 788 |
| 130. | 24.27 sq mi | Sudbury School District / 18,197 |
| 131. | 23.74 sq mi | Duxbury School District / 15,208 |
| 132. | 23.56 sq mi | Boxford School District / 8,105 |
| 133. | 23.45 sq mi | Rowe School District / 452 |
| 133. | 23.45 sq mi | Mohawk Trail School District in Rowe (7-12) / 452 |
| 135. | 23.44 sq mi | Sharon School District / 17,879 |
| 136. | 23.39 sq mi | Mashpee School District / 13,988 |
| 137. | 23.31 sq mi | Agawam School District / 28,626 |
| 138. | 23.25 sq mi | Leicester School District / 11,147 |
| 139. | 23.20 sq mi | Manchester Essex Regional School District / 8,827 |
| 140. | 23.09 sq mi | Hadley School District / 5,285 |
| 141. | 22.88 sq mi | Brewster School District / 9,858 |
| 142. | 22.83 sq mi | Chicopee School District / 55,603 |
| 143. | 22.81 sq mi | Grafton School District / 18,047 |
| 144. | 22.81 sq mi | Leverett School District / 1,836 |
| 145. | 22.69 sq mi | Swansea School District / 16,005 |
| 146. | 22.37 sq mi | Chelmsford School District / 34,495 |
| 147. | 22.25 sq mi | Methuen School District / 48,159 |
| 148. | 22.21 sq mi | Hingham School District / 22,550 |
| 149. | 22.08 sq mi | Gardner School District / 20,279 |
| 150. | 21.99 sq mi | Whitman-Hanson School District / 24,959 |
| 151. | 21.85 sq mi | Hamilton-Wenham School District / 13,137 |
| 152. | 21.78 sq mi | Pembroke School District / 18,006 |
| 153. | 21.71 sq mi | Wrentham School District / 11,169 |
| 154. | 21.43 sq mi | Greenfield School District / 17,484 |
| 155. | 21.33 sq mi | Brockton School District / 94,267 |
| 156. | 21.28 sq mi | Holyoke School District / 40,079 |
| 157. | 21.27 sq mi | North Brookfield School District / 4,715 |
| 158. | 21.22 sq mi | Lenox School District / 5,043 |
| 159. | 20.96 sq mi | Truro School District / 1,738 |
| 159. | 20.96 sq mi | Nauset/Provincetown School Districts in Turo (7-12) / 1,738 |
| 161. | 20.93 sq mi | Norwell School District / 10,651 |
| 162. | 20.88 sq mi | Harwich School District / 12,243 |
| 163. | 20.87 sq mi | Marlborough School District / 39,141 |
| 164. | 20.73 sq mi | Shrewsbury School District / 36,114 |
| 165. | 20.70 sq mi | Tewksbury School District / 29,718 |
| 166. | 20.63 sq mi | Dracut School District / 30,350 |
| 167. | 20.58 sq mi | Westborough School District / 18,481 |
| 168. | 20.44 sq mi | Walpole School District / 24,571 |
| 169. | 20.34 sq mi | North Adams School District / 13,563 |
| 170. | 20.28 sq mi | Southbridge School District / 16,775 |
| 171. | 20.13 sq mi | Whately School District / 1,384 |
| 172. | 20.09 sq mi | Mansfield School District / 23,389 |
| 173. | 20.00 sq mi | New Bedford School District / 94,873 |
| 174. | 19.87 sq mi | Acton School District / 22,614 |
| 175. | 19.85 sq mi | Foxborough School District / 17,129 |
| 176. | 19.79 sq mi | Wellfleet School District / 3,011 |
| 177. | 18.87 sq mi | North Attleborough School District / 28,779 |
| 178. | 18.80 sq mi | Canton School District / 22,036 |
| 179. | 18.69 sq mi | Richmond School District / 1,535 |
| 179. | 18.69 sq mi | Pittsfield School District in Richmond (9-12) / 1,535 |
| 181. | 18.66 sq mi | Kingston School District / 12,846 |
| 182. | 18.64 sq mi | Holliston School District / 14,008 |
| 183. | 18.48 sq mi | Northborough School District / 14,644 |
| 184. | 18.43 sq mi | Fairhaven/New Bedford School Districts in Acushnet (9-12) / 10,329 |
| 184. | 18.43 sq mi | Acushnet School District / 10,329 |
| 186. | 18.37 sq mi | Seekonk School District / 14,131 |
| 187. | 18.35 sq mi | Bellingham School District / 16,564 |
| 188. | 17.84 sq mi | Newton School District / 86,945 |
| 189. | 17.71 sq mi | South Hadley School District / 17,745 |
| 190. | 17.63 sq mi | Scituate School District / 18,240 |
| 191. | 17.36 sq mi | Mattapoisett School District / 6,138 |
| 192. | 17.26 sq mi | Northbridge School District / 16,100 |
| 193. | 17.21 sq mi | East Bridgewater School District / 13,996 |
| 194. | 16.98 sq mi | Wilmington School District / 22,907 |
| 195. | 16.82 sq mi | Weston School District / 11,704 |
| 196. | 16.79 sq mi | Weymouth School District / 54,815 |
| 197. | 16.77 sq mi | Tyngsborough School District / 11,867 |
| 198. | 16.71 sq mi | West Springfield School District / 28,554 |
| 199. | 16.57 sq mi | Quincy School District / 92,920 |
| 200. | 16.52 sq mi | Littleton School District / 9,157 |
| 201. | 16.51 sq mi | Somerset School District in Berkley (9-12) / 6,411 |
| 201. | 16.51 sq mi | Berkley School District / 6,492 |
| 203. | 16.43 sq mi | Lexington School District / 32,306 |
| 204. | 16.21 sq mi | Peabody School District / 51,868 |
| 205. | 16.13 sq mi | Chatham School District / 6,125 |
| 206. | 16.09 sq mi | Stoughton School District / 27,833 |
| 207. | 16.06 sq mi | Boylston School District / 4,399 |
| 208. | 16.00 sq mi | Halifax School District / 7,629 |
| 209. | 15.98 sq mi | Blackstone-Millville School District / 12,263 |
| 210. | 15.91 sq mi | Hatfield School District / 3,293 |
| 211. | 15.86 sq mi | Shirley School District / 7,211 |
| 211. | 15.86 sq mi | Ayer/Lunenberg School Districts in Shirley (9-12) / 7,211 |
| 213. | 15.82 sq mi | Sherborn School District / 4,200 |
| 214. | 15.73 sq mi | Wales School District / 1,923 |
| 215. | 15.71 sq mi | Millbury School District / 13,350 |
| 216. | 15.61 sq mi | Hanover School District / 14,120 |
| 217. | 15.55 sq mi | Brookfield School District / 3,396 |
| 218. | 15.48 sq mi | Auburn School District / 16,294 |
| 219. | 15.32 sq mi | West Bridgewater School District / 6,981 |
| 220. | 15.26 sq mi | Carlisle School District / 4,967 |
| 221. | 15.12 sq mi | Dover School District / 5,727 |
| 222. | 15.09 sq mi | Beverly School District / 40,370 |
| 223. | 15.05 sq mi | Wayland School District / 13,294 |
| 224. | 14.95 sq mi | Natick School District / 34,230 |
| 225. | 14.90 sq mi | Norfolk School District / 11,529 |
| 226. | 14.75 sq mi | Milford School District / 28,203 |
| 227. | 14.67 sq mi | Plympton School District / 2,840 |
| 228. | 14.40 sq mi | Medfield School District / 12,236 |
| 229. | 14.23 sq mi | Sunderland School District / 3,683 |
| 230. | 14.23 sq mi | Lincoln School District / 7,181 |
| 231. | 14.13 sq mi | Orleans School District / 5,874 |
| 232. | 14.02 sq mi | Southborough School District / 9,869 |
| 233. | 13.99 sq mi | Marion School District / 4,935 |
| 234. | 13.96 sq mi | Eastham School District / 4,932 |
| 235. | 13.82 sq mi | Erving School District / 1,832 |
| 235. | 13.82 sq mi | Gill-Montague School District in Erving (7-12) / 1,832 |
| 237. | 13.75 sq mi | Braintree School District / 36,543 |
| 238. | 13.66 sq mi | Bedford School District / 13,788 |
| 239. | 13.58 sq mi | Lowell School District / 108,491 |
| 240. | 13.46 sq mi | Middleton School District / 9,273 |
| 241. | 13.33 sq mi | Easthampton School District / 16,066 |
| 242. | 13.28 sq mi | Danvers School District / 27,075 |
| 243. | 13.19 sq mi | Gosnold School District / 99 |
| 244. | 13.14 sq mi | North Reading School District / 15,249 |
| 245. | 13.01 sq mi | East Longmeadow School District / 15,917 |
| 246. | 13.01 sq mi | Milton School District / 27,204 |
| 247. | 12.97 sq mi | Berlin School District / 2,917 |
| 248. | 12.95 sq mi | West Boylston School District / 7,792 |
| 249. | 12.86 sq mi | Georgetown School District / 8,379 |
| 250. | 12.73 sq mi | Waltham School District / 61,908 |
| 251. | 12.69 sq mi | North Adams School District in Clarksburg (9-12) / 1,580 |
| 251. | 12.69 sq mi | Clarksburg School District / 1,580 |
| 253. | 12.63 sq mi | Woburn School District / 38,826 |
| 254. | 12.37 sq mi | Webster School District / 16,806 |
| 255. | 12.33 sq mi | Fairhaven School District / 15,971 |
| 256. | 12.33 sq mi | Ashland School District / 16,985 |
| 257. | 12.29 sq mi | Holland School District / 2,491 |
| 258. | 12.29 sq mi | Needham School District / 29,540 |
| 259. | 12.26 sq mi | Amesbury School District / 16,554 |
| 260. | 12.02 sq mi | Millis School District / 8,007 |
| 261. | 11.92 sq mi | Topsfield School District / 6,286 |
| 262. | 11.73 sq mi | Burlington School District / 25,190 |
| 263. | 11.54 sq mi | Medway School District / 12,965 |
| 264. | 11.52 sq mi | Hudson School District / 19,464 |
| 265. | 11.00 sq mi | Plainville School District / 8,581 |
| 266. | 10.88 sq mi | Westwood School District / 14,809 |
| 267. | 10.79 sq mi | Saugus School District / 27,369 |
| 268. | 10.74 sq mi | Lynn School District / 91,289 |
| 269. | 10.69 sq mi | North Adams School District in Monroe (9-12) / 118 |
| 270. | 10.37 sq mi | Norwood School District / 28,844 |
| 271. | 10.32 sq mi | Rockland School District / 17,616 |
| 272. | 10.29 sq mi | Boxborough School District / 5,102 |
| 273. | 10.25 sq mi | Dedham School District / 25,111 |
| 274. | 10.02 sq mi | Wellesley School District / 28,858 |
| 275. | 9.95 sq mi | Reading School District / 25,176 |
| 276. | 9.88 sq mi | Lynnfield School District / 12,058 |
| 277. | 9.83 sq mi | Randolph School District / 33,135 |
| 278. | 9.79 sq mi | Cohasset School District / 8,100 |
| 279. | 9.67 sq mi | Provincetown School District / 2,959 |
| 280. | 9.65 sq mi | Abington School District / 16,081 |
| 281. | 9.12 sq mi | Longmeadow School District / 15,858 |
| 282. | 8.92 sq mi | Ayer School District / 7,427 |
| 283. | 8.35 sq mi | Newburyport School District / 17,662 |
| 284. | 8.28 sq mi | Salem School District / 42,321 |
| 285. | 8.10 sq mi | Medford School District / 56,981 |
| 286. | 7.90 sq mi | Somerset School District / 18,262 |
| 287. | 7.36 sq mi | Wakefield School District / 25,835 |
| 288. | 7.31 sq mi | Oak Bluffs School District / 4,599 |
| 289. | 7.25 sq mi | Holbrook School District / 10,925 |
| 290. | 6.99 sq mi | Rockport School District / 7,078 |
| 291. | 6.93 sq mi | Lawrence School District / 77,364 |
| 292. | 6.75 sq mi | Brookline School District / 59,016 |
| 293. | 6.54 sq mi | Tisbury School District / 4,036 |
| 294. | 6.39 sq mi | Cambridge School District / 106,844 |
| 295. | 6.03 sq mi | Winchester School District / 21,863 |
| 296. | 6.02 sq mi | Stoneham School District / 21,611 |
| 297. | 5.69 sq mi | Revere School District / 53,258 |
| 298. | 5.65 sq mi | Clinton School District / 13,675 |
| 299. | 5.21 sq mi | Maynard School District / 10,314 |
| 300. | 5.17 sq mi | Hopedale School District / 5,934 |
| 301. | 5.15 sq mi | Arlington School District / 43,728 |
| 302. | 5.04 sq mi | Malden School District / 60,309 |
| 303. | 4.68 sq mi | Melrose School District / 27,509 |
| 304. | 4.65 sq mi | Belmont School District / 25,173 |
| 305. | 4.39 sq mi | Marblehead School District / 20,163 |
| 306. | 4.29 sq mi | Avon School District / 4,421 |
| 307. | 4.12 sq mi | Somerville School District / 77,560 |
| 308. | 3.99 sq mi | Watertown School District / 32,880 |
| 309. | 3.43 sq mi | Everett School District / 42,758 |
| 310. | 3.02 sq mi | Swampscott School District / 13,912 |
| 311. | 2.80 sq mi | Hull School District / 10,324 |
| 312. | 2.21 sq mi | Chelsea School District / 37,084 |
| 313. | 1.97 sq mi | Winthrop School District / 17,992 |
| 314. | 1.05 sq mi | Nahant School District / 3,451 |
| 314. | 1.05 sq mi | Swampscott School District in Nahant (7-12) / 3,451 |
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.
