It was listed on the National Register of Historic Places in 2000[1] as a good example of privately organized 19th century urban planning.

Originally much larger in size than today, several neighboring communities broke off from the town during the 18th and 19th centuries, reducing it to one of Connecticut's smallest municipalities by area.

The point to the north of the confluence of the Naugatuck and Housatonic Rivers was privately developed in the 1830s by Anson Phelps and Sheldon Smith, businessmen who sought to revive the city's flagging economy with industrial development.

Approximately half the street frontage flanking the green is lined by churches and their associated parsonages and rectories.

The other main civic building is the Sterling Opera House, built in 1889 on Elizabeth Street to a design by H. Edwards Ficken.