The Town of Cheshire can trace it's roots indirectly from the town of New Haven by way of Wallingford, 2 generations removed. Today it is still a home to many people who commute daily to the new Haven area for work. Originally founded as the West Farm area of Wallingford, if got it's official name of Cheshire from a the Brooks family who emigrated here from Cheshire in England.
The early settlers were not only farmers but also were extensively into the mining of copper and barium sulfite, which was used extensively in the production of glass, paint and cloth. The first manufacturing company to start up in Cheshire, was aptly called the Cheshire Mfg Co, which produced ivory combs and buttons. Part of the original company, which was called the Ball & Socket Co, has been merged with the Waterbury Co, but still produces military buttons for our armed services.
Sales data for 2009 is as follows:
| CY 2008 | CY 2009 | Current active | Mos of Inventory | Currently under contract | |
| RESIDENTIAL | 205 | 187 | 136 | 11 | 33 |
| CONDOS | 59 | 75 | 44 | 6 | 15 |
In 2009, 205 residential properties were sold with a range in value from $ 80,500 to $1,350,000 with a median sales price of $373,000. Days on market avg of 56
By comparison, there were 187 units sold in 2008 with a range in value from $184,000 to $1,270,000 with a median sales price $380,000. Days on market avg of 51.
Cheshire still enjoys somewhat of a manufacturing base in the north end of town. There are still several active truck farms in town. In addition, Cheshire is known s the bedding capital of New England with many nurseries located throughout the town. The old trolley line, once know as the Farmington line has since been cleaned, cleared and paved and servers as a walking and activities trail running almost 8 miles through the town.
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