House at 95 Chestnut Street

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 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.

The House at 39 Converse Street in Wakefield, Massachusetts, United States, is a well-preserved Queen Anne Victorian house. It was built c. 1880 as part of a real estate development along Converse Street. It is a 2+1⁄2-story wood-frame structure, with a hip roof and cross gable. It features decorative shingle bands in sections on the second floor, and between the first and second floors. The L-shaped house has a second story projecting gabled section over a rounded projecting bay on the first floor.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 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 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 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 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 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 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.