Captain Goodwin–James Eustis House

The William Stimpson House is a historic house at 22 Prospect Street in Wakefield, Massachusetts. The 2+1⁄2-story timber-frame house was built sometime before 1795, probably by William Stimpson, son of the local doctor. It has conservative Federal styling, most notably due to its central chimney rather than the more typical twin chimneys of the period. The building's internal layout and two kitchen fireplaces suggest that it was built as a two-family residence.The house was listed on the National Register of Historic Places in 1989.

The Deacon Thomas Kendall House is a historic house at One Prospect Street in Wakefield, Massachusetts. This timber frame, 2+1⁄2-story five-bay house has Federal styling, but its massive central chimney indicates that parts of the house likely predate the Federal period, and in a style that predates 1750 (Dea. Kendall lived 1618–1681). The house is believed to have suffered fire damage in 1786 and been reconstructed at that time, incorporating salvaged materials. Its exterior trim exhibits several different styles, that on the north and west sides more finely carved. The second-floor windows on the south side are smaller and set near the eaves, a typical colonial period feature. The house was listed on the National Register of Historic Places in 1989.Deacon Thomas Kendall was an influential member of the community, serving as a selectman, commissioner, and deacon of the church for 36 years. He and his wife, Rebecca, had 10 children, and when she died, at the age of 85, she had 175 grandchildren and great-grandchildren. The Kendalls were among the earliest settlers of the Reading area (of which Wakefield was a part until the 19th century). The house was owned for much of the 19th century by the Emerson family, who also owned it at the time of the 1786 fire.

The West Ward School is a historic school at 39 Prospect Street in Wakefield, Massachusetts. Built in 1847, it is the only surviving Greek Revival schoolhouse (of four built) in the town. The building was listed on the National Register of Historic Places in 1989. It is now maintained by the local historical society as a museum property.

The House at 2 Nichols Street in Wakefield, Massachusetts, is a well-preserved, architecturally eclectic house built in the 1890s. The 1+1⁄2-story frame house has elements of the Tudor Revival, Queen Anne, and Shingle styles, and is one of two identical houses built by local builder Berndt Heurlin. It has a hip roof, but transverse gables, one of which has a rounded bay, giving it a Queen Anne feel. The foundation exterior is fieldstone, and there are several stained glass windows.The house was listed on the National Register of Historic Places in 1989.The house was also the childhood home of the renowned Swedish-American artist, Magnus Colcord Heurlin (July 5, 1895 – March 10, 1986). Colcord Heurlin attended the Fenway School of Illustration in Boston, MA, where he studied under Harold Mathews Brett (1880-1955), the director of the newly opened school. Heurlin began illustrating covers for pulp magazines in the 1920s and 1930s and later joined the WPA Federal Arts Project, creating two murals for the Bedford Elementary School in Westport, CT. But he is best known for his vivid, oil-pastel depictions of Alaskan natives and early settler life in northern Alaska.

Temple Israel Cemetery is a historic Jewish cemetery on North Avenue in Wakefield, Massachusetts. The cemetery was established by the Temple Israel congregation of Boston in 1859. Unlike the adjacent Lakeside Cemetery, whose landscape is of winding paths, this cemetery is laid out in a rectilinear grid. Stones are somewhat uniform in their content, often listing places of birth and death. Markers placed early in the cemetery's history are predominantly marble, while many of those placed in the 20th century are granite or limestone. The cemetery's most notable burial is that of Rabbi Joshua Liebman.The cemetery was listed on the National Register of Historic Places in 1989.

The Beacon Street Tomb is a historic receiving tomb in the Lakeside Cemetery of Wakefield, Massachusetts. Built about 1858, it is one of the finest examples of Greek Revival architecture. It was listed on the National Register of Historic Places in 1989.

The House at 509 North Avenue in Wakefield, Massachusetts is a small Greek Revival cottage. The single story wood-frame house was built c. 1848 and moved to its present location c. 1869. The house is three bays wide and one deep, and exhibits very simple Greek Revival styling, including a boxed cornice and simple door and window surrounds. This house was probably built on land subdivided from holdings of ice companies working on nearby Lake Quannapowitt. Its earliest documented resident was listed in the town's 1869 directory as a shoemaker.The house was listed on the National Register of Historic Places in 1989.

The Church–Lafayette Streets Historic District encompasses a well-preserved collection of late 18th- and early 19th-century houses in Wakefield, Massachusetts. It includes properties on Church Street between Common Street and North Avenue, and on Lafayette Street between Common and Church Streets. The district was added to the National Register of Historic Places in 1989.

The Lakeside Cemetery Chapel is a historic chapel in Lakeside Cemetery, on North Avenue in Wakefield, Massachusetts. The stone chapel, built 1913, is one of a few Neo-Gothic buildings in the town. Roughly resembling English country churches, the building has a steeply pitched slate roof, with sidewalls containing supporting buttresses. The front and rear of the chapel both have projecting entry sections that repeat the sharply pitched gable.The chapel was listed on the National Register of Historic Places in 1989.

The Jonas Cowdry House is a historic house at 61 Prospect Street in Wakefield, Massachusetts. Built c. 1833, the Federal style wood-frame house is three bays wide and four deep, a significant local variant to conventional Federal style architecture. The house was listed on the National Register of Historic Places in 1989.

The Suell Winn House is a historic house at 72-74 Elm Street in Wakefield, Massachusetts. The house was built c. 1805 for Major Suell Winn, a local farmer, and is one of the best representatives of Federal-style architecture in Wakefield. It is a 2+1⁄2-story wood-frame structure, with two interior chimneys, a five-bay facade, and an elegant doorway with sidelight windows and an architrave. An ell extends the house to the right. Winn, a native of nearby Burlington, was killed crossing the railroad that divided his landholdings, after attending a town meeting where he protested the need for improved crossing signals at that location.The house was listed on the National Register of Historic Places in 1989.

95 Chestnut Street is a historic house located in Wakefield, Massachusetts. It is significant as an example of a well-preserved vernacular Greek Revival style house.