Dan Raymond House
Built about 1775 of home made brick by the "notorious" and "cunning" character, Dan Raymond, this home decried as "extravagant" in its time, would now be considered an unpretentious brick colonial. Except for an added ell, the house is nearly the same as during the Revolution when it was one of Sheffield's finest homes. The house is furnished with artifacts representative of Dan Raymond's time. The Museum shop is located in the Dan Raymond House.

Parker Hall Law Office
This two-room office, built about 1820, served three lawyers throughout the 19th century. In the mid 1970's, this building was rescued by the Historical Society and moved to its present location. The Parker Hall Law Office was listed in 1935 on the Historic American Buildings Survey.

Carriage House
This two-story c.1870 clapboard structure now serves as the site of a tool exhibit that showcases a variety of ingenious devices used in rural farms and in households of generations past.

Education Center
Fulfilling many purposes over the decades, this structure dating to 1876 owes its unusual shape to its function as a Victorian vegetable growing house that provided fresh greens in all seasons. It is now used as an education center for classes and workshops.

Mark Dewey Hatter’s Shop
Originally constructed about 1816 to serve as a hat and cap manufactory for Mark Dewey and his three young apprentices, the structure was rescued by the Society in the 1980’s and now serves as the Mark Dewey Research Center. While conducting his hat and cap business, Dewey lived next door in the Dan Raymond House. He sold the house and shop in 1828.

Smokehouse
Constructed about 1838 by Edward Fellows Ensign, the smokehouse was donated to the Society, moved in 2000 to its present location and restored. It is a rare example of a double chamber smokehouse and possibly was used to supply the needs not only of the Ensign family but also the inventory needs of the Old Stone Store, a country general store, which was owned by the same family. It is in working condition.

Old Stone Store
The Old Stone Store is the oldest existing mercantile establishment in Sheffield and was build circa 1834 by Major Eli Ensign with distinctive stone from a local quarry. Sitting as it does beside the 18th century meetinghouse and immediately in front of the 19th century town hall, it occupies an important location in the community, not only historically but also geographically. Rescued by the Society in 1999, it is presently undergoing extensive renovation and will open as a museum, exhibit space and information center in 2002.