The first Academy building in Orange was constructed about 1821, across from Orange Green. In 1878-1879, a larger building replaced it. The second floors of both successive buildings were used for the school, while the first floors were used as assembly rooms by the town. In the twentieth century, town offices began moving into the building, which was enlarged to the rear. Administrative use by town government continued until a new Town Hall was built in 1967. The building next served as offices for the town’s Board of Education until 1989. Since then, the Academy has been leased to the Orange Historical Society for use as a museum.
The Federal-style house at 603 Orange Center Road in Orange, which dates to around 1800, was the first house to be built on Orange Center Green. Records indicate that the property was owned by Benjamin Clark in 1810 and it has remained in the Clark family ever since. The Clark farm, known as Maple View Farm, was established in the 1790s. A working dairy and produce farm, it now provides horse-related activities for the public.
The first meetinghouse in North Milford, now Orange, was constructed on the north end of what is now Orange Center Green in 1792. At that time, residents of Orange were still members of the Milford Congregational Church, but a separate Ecclesiastical Society was eventually formed in 1804. The separate Town of Orange was incorporated in 1822. The current Orange Congregational Church, designed by David Hoadley, was built in 1810-1811.
The Town of Orange was incorporated in 1822 and soon new buildings began to be constructed in the vicinity of the new town’s Green. The Stone-Otis House was one such structure, built around 1830 for Dennis Stone. A prominent citizen, Stone owned the town’s second general store, located in his home. Around 1840, he added a large front display window to the house for the store. Stone and his family later moved to Kansas. The house, which is transitional between the Federal and Greek Revival styles, was sold Phoebe and Charles Otis, a tool and dye maker, in 1887. The family sold the house to the town in 1966. The restored house is now a museum and the headquarters of the Orange Historical Society.