House at 39 Converse Street

The Dr. Charles Jordan House is a historic house at 9 Jordan Avenue in Wakefield, Massachusetts. Built c. 1885, it is one Wakefield's most elaborate Queen Anne Victorian houses. The 2+1⁄2-story wood-frame house is unusual for having a hipped roof; it also has a tower in the northwest corner, and a porch with Italianate pillars brackets. The house was built by Dr. Charles Jordan, a local physician and pharmacist with extensive land holdings in the area.The house was listed on the National Register of Historic Places in 1989.

The H. M. Warren School is a historic school building at 30 Converse Street in Wakefield, Massachusetts. Built c. 1895–1897, it is locally significant as a fine example of Renaissance Revival architecture, and for its role in the town's educational system. The building was listed on the National Register of Historic Places in 1989. It now houses social service agencies.

Wakefield Park Historic District is a residential historic district encompassing a portion of a late-19th/early-20th century planned development in western Wakefield, Massachusetts. The district encompasses sixteen properties on 8 acres (3.2 ha) of land out of the approximately 100 acres (40 ha) that comprised the original development. Most of the properties in the district are on Park Avenue, with a few located on immediately adjacent streets.The Wakefield Park development was laid out 1888 by J. S. Merrill, a local developer, on land southwest of the town center that had been used as farmland until the 1850s. Merrill developed some of the properties himself, and instituted deed restrictions on the sale of lots to ensure that the area would contain only high quality upper-middle-class homes. In the 1890s, when development in the area was at its peak, Merrill partnered with Charles Hanks, who successfully marketed the development as a healthy "garden suburb" alternative to city living.Architecturally, the houses that were built exhibited a variety of styles popular around the turn of the 20th century, often mixing architectural elements from different styles. One example of this eclecticism is the house at 8 Park Avenue: built c. 1900, it is a 2+1⁄2-story wood-frame house with a steeply pitched Colonial Revival-style roof, but with an entrance that is stylistically Craftsman/Bungalow. Its corner tower is typical of Queen Anne Victorians. A number of houses, including thouse at 2 and 4 Park, combine Shingle and Colonial Revival styles, while 24 Park is a more typical Queen Anne Victorian.The district was listed on the National Register of Historic Places in 1990.

The Charles Winship House was a historic house located at 13 Mansion Road and 10 Mansion Road in Wakefield, Massachusetts. The 2+1⁄2-story mansion (for which the road is named) was built between 1901 and 1906 for Charles Winship, proprietor (along with Elizabeth Boit) of the Harvard Knitting Mills, a major business presence in Wakefield from the 1880s to the 1940s. It was the town's most elaborate Colonial Revival building, featuring a flared hip roof with a balustrade on top, and a two-story portico in front with composite capitals atop fluted columns.The house was listed on the National Register of Historic Places in 1989.The architect of the house was the Boston-based firm Hartwell & Richardson. The ornate interior was designed by the firm Irving and Casson – A. H. Davenport Co.. Both firms were famous for their meticulous design as well as high quality of workmanship and materials. During The Winship House's construction in 1902, Irving and Casson – A. H. Davenport Co. was commissioned for work on the White House renovation.

The House at 6 Adams Street in Wakefield, Massachusetts is one of the best examples of Shingle style architecture in the town. It was designed by Boston architect Robert Pote Wait and built in 1885–86 to be his own home. It was listed on the National Register of Historic Places in 1989.

The House at 1 Morrison Avenue is one of a few Tudor Revival houses in Wakefield, Massachusetts. The 2+1⁄2-story wood-frame house has a hip roof with a copper crest, central dormer, and a larger projecting gable section on the left. The single story porch wraps around two sides of the house, and features a high gable over the front stairs which is decorated with bargeboard and half timbers. It was built c. 1890 on land that had been acquired and subdivided by J.S. Merrill and Charles Hanks as part of the major Wakefield Park subdivision.The house was listed on the National Register of Historic Places in 1989.

Our Lady of Nazareth Academy was a private, all-girls, Roman Catholic high school in Wakefield, Massachusetts. It was located in the Roman Catholic Archdiocese of Boston and operated from 1947 to 2009.

The House at 32 Morrison Road in Wakefield, Massachusetts is a well-preserved, architecturally eclectic, house in the Wakefield Park section of town. The 2+1⁄2-story wood-frame house features a gambrel roof with a cross gable gambrel section. Set in the front gable end is a Palladian window arrangement. The porch has a fieldstone apron, with Ionic columns supporting a pedimented roof. Above the front entry rises a two-story turret with conical roof. The house was built c. 1906–08, as part of the Wakefield Park subdivision begun in the 1880s by J.S. Merrill.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.

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 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 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.