House at 22 Parker Road

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 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.

The House at 13 Sheffield Road in Wakefield, Massachusetts is a well-preserved Craftsman/Bungalow style house. The 1+1⁄2-story house was built c. 1918 out of fieldstone with a stucco exterior. The roof has extended eaves with exposed purlins, and a large cross-gable section on the right side. Strapwork on the walls give the house a Tudor Revival appearance. The subdivision in which it was built was laid out in 1916 in an area known as Cowdrey's Hill, after an early settler.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 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 House at 30 Sheffield Road is one of the more creative early 20th-century Craftsman style houses in Wakefield, Massachusetts. The 1+1⁄2-story house was built (c. 1916) predominantly of fieldstone and finished in stucco, and was one of the first houses built in the Sheffield Road subdivision. The main body of the house as a gable roof, with two cross-gable sections facing front sheltering porches set on heavy columns. The entry is in the center of the front facade, topped by a small gable end, and with a small pergola in front.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 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.

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.

The House at 20 Morrison Road in Wakefield, Massachusetts is a well-preserved Colonial Revival house. The 2+1⁄2-story wood-frame house originally had a semicircular portico, a relative rarity in Wakefield. The porch has turned balusters, and the three roof dormers have pedimented gable ends. The house was built about 1890 on land originally part of the large estate of Dr. Charles Jordan, that was developed in the 1880s as Wakefield Park.The house was listed on the National Register of Historic Places in 1989.

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.