House at 5 Bennett Street

The Massachusetts State Armory is a historic armory in Wakefield, Massachusetts. Built in 1913, it is a fine local example of Classical Revival architecture, and a symbol of the town's long military history. The building was listed on the National Register of Historic Places in 1989. It presently houses the Americal Civic Center, a local community center.

The Michael Sweetser House is a historic house at 15 Nahant Street in Wakefield, Massachusetts. The 2+1⁄2-story timber-frame house was built c. 1755 by Michael Sweetser, an early settler of the area. It is traditionally Georgian in character, although its front door surround was added during Greek Revival period of the mid 19th century. One of the house's 19th century occupants was Paul Hart Sweetser, one of the founders of the Massachusetts Teachers Association and a locally active politician.The house was listed on the National Register of Historic Places in 1989.

The House at 12 West Water Street in Wakefield, Massachusetts is a rare local example of a Second Empire house. The wood-frame house was built around 1860, and has two full stories, and a third beneath the mansard roof. It is three bays wide, with a wide double-door entry, and a porch across the front with elaborately decorated posts. The house may have been built by Cyrus Wakefield, owner of the Wakefield Rattan Company, and sold to a company employee. A later owner was George Cox, who owned a billiard parlor in the town center.The house was listed on the National Register of Historic Places in 1989.

Wakefield Centre station is a former railway station at 57 Water Street (Route 129) in Wakefield, Massachusetts. Built in the early 1870s, it is a surviving element of the railroad infrastructure that enabled Wakefield's growth as an industrial center in the late 19th century. The depot was added to the National Register of Historic Places in 1989 as Centre Depot. As of 2008, the former depot serves as a restaurant.

40 Crescent Street is a historic house in Wakefield, Massachusetts, and is significant as a particularly fine example of a Greek Revival style house.

The Item Building is a historic commercial building at 26 Albion Street in Wakefield, Massachusetts. Built in 1912, the single-story brick building serves as the headquarters of The Wakefield Daily Item, Wakefield's main community newspaper, and is a well-kept example of early 20th century commercial architecture.

South Reading Academy is a historic former school building at 7 Foster Street in Wakefield, Massachusetts, US. Built in 1828–29 for the First Baptist Church, the building has served as a religious school, public high school, clubhouse, and commercial space. The building was listed on the National Register of Historic Places in 1989.

The Dr. S. O. Richardson House is a historic house at 694 Main Street in Wakefield, Massachusetts, United States. Built in the late 1830s, this wood-frame house is one of the finest Greek Revival houses in Wakefield, and was the home of Dr. Solon O. Richardson, a locally prominent physician and real estate developer. The house was listed on the National Register of Historic Places in 1989.

The Wakefield Rattan Company was the world's leading manufacturer of rattan furniture and objects in the second half of the 19th century. Founded by Cyrus Wakefield in 1851 in South Reading, Massachusetts (now Wakefield), it perfected machinery for working with rattan, developing looms for weaving chair seats and mats. Its products also included wicker furniture and baby carriages. The company also successfully found uses for previously wasted portions of the plant, using shavings to create baling fabric and floor coverings. Its products were available throughout the United States.

The Wakefield Trust Company is a historic commercial building at 371 Main Street in Wakefield, Massachusetts. Built in 1924, it is one of three buildings on the west side of Main Street (along with the library and main post office) that give the town center a strong Classical Revival flavor. The building was listed on the National Register of Historic Places in 1989.

The buildings at 35–37 Richardson Avenue are historic rowhouses in Wakefield, Massachusetts. These two rowhouses, built c. 1912–15, are among the earliest apartment blocks built in the town. They were built by Solon O. Richardson, Jr. on a portion of his estate. The buildings were listed on the National Register of Historic Places in 1989.

Flanley's Block is a historic commercial building at 349–353 Main Street in Wakefield, Massachusetts, US. Built about 1895, it is a well-preserved local example of late 19th-century Italianate commercial architecture. The building was listed on the National Register of Historic Places in 1989.