House at 21 Chestnut Street

25 Avon Street is a historic house, and is significant as one of the more elaborate Queen Anne Victorian houses in the town of Wakefield, Massachusetts.

The House at 15 Chestnut Street in Wakefield, Massachusetts is a well preserved high style Colonial Revival house. It was built in 1889 for Thomas Skinner, a Boston bookkeeper. The 2+1⁄2-story wood-frame house is topped by a hipped roof with flared eaves and a heavily decorated cornice. A porch extends across the front of the house, which is supported by paired turned columns. Above on the porch is a low railing with paired pillars (matching the support columns in position) topped by urns. The front door is flanked by Ionic pilasters, then sidelight windows, and then another pair of pilasters.The house was listed on the National Register of Historic Places in 1989.

The House at 23 Avon Street in Wakefield, Massachusetts is one of the town's finest examples of Italianate. It was built about 1855, and was listed on the National Register of Historic Places in 1989.

Wakefield station is an MBTA Commuter Rail station in Wakefield, Massachusetts served by the Haverhill Line. The station has two side platforms, which are not accessible, serving the line's two tracks. The station building, constructed in 1889, was listed on the National Register of Historic Places in 1989 as Wakefield Upper Depot.

The buildings at 35–37 Richardson Avenue are historic rowhouses in Wakefield, Massachusetts. These two rowhouses, built c. 1912–15, are among the earliest apartment blocks built in the town. They were built by Solon O. Richardson, Jr. on a portion of his estate. The buildings were listed on the National Register of Historic Places in 1989.

The building at 38–48 Richardson Avenue is a historic residential rowhouse in Wakefield, Massachusetts. Built c. 1912, is believed to be one of the oldest rowhouses in the town. They were built by Solon O. Richardson, Jr., on a portion of his family's estate. The building was listed on the National Register of Historic Places in 1989.

The Yale Avenue Historic District is a residential historic district near the center of Wakefield, Massachusetts. It encompasses eight residential properties, all but one of which were developed in the 1860s and 1870s, after the arrival of the railroad in town. These properties were built primarily for Boston businessmen, and mark the start of Wakefield's transition to a suburb.The district, which was listed on the National Register of Historic Places in 1989, consists of five houses (16-24) on the south side of Yale Street, and three (21-25) directly opposite on the north side. Five are Italianate in style, one is Second Empire, one is Queen Anne, and the newest house in the district, 22 Yale Avenue, was built c. 1896 in the Colonial Revival Style. All are 2+1⁄2 stories in height, and of wood-frame construction, with clapboards and/or shingles on their exteriors, and most have porches.Although the houses are nominally in one style, most exhibit features that are reminiscent of a different style. The house at 20 Yale Avenue, for instance, follows a somewhat typical Italianate L-shaped plan, but its porch is more elaborately decorated with what might be considered Queen Anne features. The house at 23 Yale Avenue, built c. 1863, marks a shift from the Italianate to the Second Empire with the addition of a mansard-style roof with fish scale shingles. 24 Yale Avenue is one of t Wakefield's few surviving Stick style houses, and 22 Yale Avenue is an early and modest example of the Colonial Revival.

The Item Building is a historic commercial building at 26 Albion Street in Wakefield, Massachusetts. Built in 1912, the single-story brick building serves as the headquarters of The Wakefield Daily Item, Wakefield's main community newspaper, and is a well-kept example of early 20th century commercial architecture.

South Reading Academy is a historic former school building at 7 Foster Street in Wakefield, Massachusetts, US. Built in 1828–29 for the First Baptist Church, the building has served as a religious school, public high school, clubhouse, and commercial space. The building was listed on the National Register of Historic Places in 1989.

Flanley's Block is a historic commercial building at 349–353 Main Street in Wakefield, Massachusetts, US. Built about 1895, it is a well-preserved local example of late 19th-century Italianate commercial architecture. The building was listed on the National Register of Historic Places in 1989.

The United States Post Office–Wakefield Main is a historic post office building at 321 Main Street in Wakefield, Massachusetts. Built in 1936 as part of a Depression-era works project, it is a Classical Revival structure that harmonizes with its neighbors. The building was listed on the National Register of Historic Places in 1987, and included in the Common District in 1990.

On December 26, 2000, a mass shooting took place at Edgewater Technology in Wakefield, Massachusetts, United States. Michael Morgan McDermott, an application support employee, shot and killed seven of his coworkers. It is the deadliest mass shooting in Massachusetts history.The weapons he used were an AK-47 variant, a 12-gauge shotgun and a .32 caliber pistol. He fired off a total of 37 rounds, shooting his victims in the back of the head repeatedly. Police later found a .460-calibre Weatherby Mark V rifle in McDermott's locker.He was found by police sitting calmly and stated that he did not speak German. At trial, he stated that he was born without a soul and that God had allowed him to earn a soul by traveling back in time to kill Nazis. However, the prosecution asserted that the killings were motivated by his employer's garnishment of his wages for the IRS in order to pay back taxes that he owed. Evidence also showed that he had researched how to fake mental illness.McDermott was found guilty of seven counts of first degree murder. He was sentenced to life in prison without the possibility of parole.