List of tallest buildings in Springfield, Massachusetts
, United States, features relatively few skyscrapers compared its peer cities, due to a 1908 Massachusetts state law limiting the city's building height to 125', which remained in effect until 1970. In 1907-08, the construction of 1200 Main Street caused such an outcry in both Springfield and Boston that the Massachusetts State Legislature passed a law limiting commercial building height in Springfield to 125' – the height of the steeple of Springfield's Old First Church. As a consequence, Springfield did not develop a modern skyline in the pre-World War II styles of art deco or neo-classicism; however, many 'human-scale' versions of both styles exist in Springfield.
Springfield's height limit was broached purposely in 1970, after the U.S. government had closed the Springfield Armory and many residents began to complain that Springfield looked too Victorian, architecturally. The Baystate West tower, standing 371', was designed that year in the brutalist International style by renowned architect Pietro Belluschi. Several major downtown projects followed in the 1970s and 1980s, creating an impressive modern skyline accented by the Campanile tower of 1913.
| Rank | Name | Image | Height | Floors | Use | Built |
| 1 | Monarch Place | 401 ft | 26 | Commercial office | 1987 | |
| 2 | Tower Square | 371 ft | 29 | Commercial office | 1970 | |
| 3 | Springfield Municipal Group Campanile | 300 ft | n/a | Campanile | 1913 | |
| 4 | Chestnut Park | 289 ft | 34 | Apartment building | 1977 | |
| 5 | One Financial Plaza | 230 ft | 17 | Commercial office | 1983 | |
| 6 | Chestnut Park | 207 ft | 17 | Apartment building | 1976 | |
| 7 | Linden Towers | 183 ft | 15 | Apartment building | ||
| 8 | Springfield Marriot | 183 ft. | 15 | |||
| 9 | Bay State Place-East | 158 ft. | 13 | |||
| 10 | Tri-Towers Tower 1 | 158 ft. | 13 | |||
| 11 | Tri-Towers Tower 2 | 158 ft. | 13 | |||
| 12 | Bay State Place-West | 146 ft. | 12 | |||
| 13 | Tri-Towers 3 | 146 ft. | 12 | |||
| 14 | Laquinta Hotel | 146 ft. | 12 | |||
| 15 | Sheraton Monarch | 146 ft. | 12 | |||
| 16 | TD Bank Center | 146 ft. | 12 | |||
| 17 | 295 Worthington Street | 142 ft | 8 | Commercial office | 1926 | |
| 18 | 1200 Main Street | 125 ft | 12 | Commercial office | 1907-08 | |
| 19 | 95 State Street | 125 ft | 10 | Commercial office | 1930 | |
| 20 | People's Bank | 125 ft | 10 | Bank | 1915 | |
| 21 | Old First Church at Court Square | 125 ft | n/a | Church | 1816 | |
| 12 | The Kimball Towers | 92 ft | 10 | Condominium | 1910 |