Buildings at 35–37 Richardson Avenue

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 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.

The House at 21 Chestnut Street is one of the best preserved Italianate houses in Wakefield, Massachusetts. It was built c. 1855 to a design by local architect John Stevens, and was home for many years to local historian Ruth Woodbury. The house was 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 House at 12 West Water Street in Wakefield, Massachusetts is a rare local example of a Second Empire house. The wood-frame house was built around 1860, and has two full stories, and a third beneath the mansard roof. It is three bays wide, with a wide double-door entry, and a porch across the front with elaborately decorated posts. The house may have been built by Cyrus Wakefield, owner of the Wakefield Rattan Company, and sold to a company employee. A later owner was George Cox, who owned a billiard parlor in the town center.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.

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 Wakefield Trust Company is a historic commercial building at 371 Main Street in Wakefield, Massachusetts. Built in 1924, it is one of three buildings on the west side of Main Street (along with the library and main post office) that give the town center a strong Classical Revival flavor. 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 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.