House at 2 Nichols Street

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 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 Nathaniel Cowdry House is a historic house at 71 Prospect Street in Wakefield, Massachusetts. Built about 1764, it is one of Wakefield's oldest buildings, built by a member of the locally prominent Cowdry family, who were early settlers. The house was listed on the National Register of Historic Places in 1989.

The Captain Goodwin–James Eustis House is a historic house in Wakefield, Massachusetts. Built about 1760 and enlarged around 1830, it is a good local example of Greek Revival architecture, which was owned by a prominent local businessman and civic leader. The house was listed on the National Register of Historic Places on March 2, 1990, where it is listed as the "Captain Goodwin–James Custis 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 House at 88 Prospect Street in Wakefield, Massachusetts is one of three houses in the family compound of Elizabeth Boit. Built in 1913, the compound of which this house is a part is the only estate of one of Wakefield's major industrial figures to survive. 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.

The House at 90 Prospect Street in Wakefield, Massachusetts is one of three houses in the family compound of Elizabeth Boit. Built in 1913, the compound of which this house is a part is the only estate of one of Wakefield's major industrial figures to survive. The house was listed on the National Register of Historic Places in 1989.

The Elizabeth Boit House is a historic house at 127 Chestnut Street in Wakefield, Massachusetts. Elizabeth Boit, co-founder of the Harvard Knitting Mills, also built on the west side, creating an estate compound on the summit of Cowdry's Hill that included three residences, formal gardens, a playhouse, and greenhouse. All three residences, 88 and 90 Prospect Street, and 127 Chestnut Street (1910-1913), were designed in the English Cottage style by Wakefield architect Harland Perkins. The stucco structures have red tile roofs, recessed entries, exposed purlins, and irregular fenestration. This, the main house is 2+1⁄2 stories in height, with an angled three-part layout, and is oriented toward the courtyard formed by the three buildings.This house was listed on the National Register of Historic Places in 1989, for its architecture, and for its association with Elizabeth Boit. She was one of the first highly placed female executives in the male-dominated management ranks of textile firms of the period, and is believed to be the only woman in a top executive position in the United States textile industry in 1923. She pioneered improvements in worker conditions, offering health care to factory workers and providing bonuses based on company profits. The compound she built at Chestnut and Prospect Streets is the only surviving estate of Wakefield's leading business executives. The home was listed for sale on September 16, 2021, for $1,990,000 and sold on November 4, 2021, for $2,750,000.

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 House at 22 Parker Road is one of a few high style Colonial Revival houses in Wakefield, Massachusetts. The 2+1⁄2-story wood-frame house is estimated to have been built in the 1880s. It has a hip roof, corner pilasters, and gable end dormers, the center one having a swan-neck design. The main facade is divided into three sections: the leftmost has a rounded bay with three windows on each level, and the right section has a Palladian window configuration on the first floor, and a pair of windows on the second. The central section has the front door, sheltered by a porch that wraps around to the right side, flanked by sidelights and topped by a fanlight. Above the front door is a porch door flanked by wide windows and topped by a half-round window with Gothic style insets.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.