Hillside Avenue Historic District (Medford, Massachusetts)

The Lawrence Light Guard Armory is a historic armory building at 92 High Street in Medford, Massachusetts. The three-story granite and brick building was built in 1891 to a design by Shepley, Rutan and Coolidge. The Romanesque Revival building has massive granite quoins on the corners, a granite course between the first and second floors, and granite lintel sections above its windows. The entrance, centered on the north facade, is flanked by round turrets with crenellated tops.The building was listed on the National Register of Historic Places in 1975.

The Medford Pipe Bridge is a historic plate girder pipeline bridge over the Mystic River, between S. Court St. and the Mystic Valley Parkway in Medford, Massachusetts. It was built in 1897 as part of the Metropolitan Water Board's northern high and low service. The bridge carries a 20" high-service pipe and a 48" low-service pipe between the Chestnut Hill Reservoir and Spot Pond that are cross connected with the Mystic Water Works pumping station in Somerville. The bridge was built by the New Jersey Steel & Iron Company in Trenton, New Jersey, and placed on abutments designed by Cheney & Trumbull. It also carries foot traffic.The bridge was listed on the National Register of Historic Places in 1990. A postcard ca. 1938 calls it the "Foot Bridge over Mystic River", Medford, Mass.

The Isaac Hall House is a historic house located at 43 High Street in Medford, Massachusetts.

The John B. Angier House is a historic house located at 129 High Street in Medford, Massachusetts.

The Jonathan Wade House is a historic First Period house at 13 Bradlee Road in Medford, Massachusetts. It is one of a handful of houses in the city with brickwork from the 17th century (the other two known survivors are the Isaac Royall House and the Peter Tufts House). A brick house is known to have been standing on this site in 1689, when Jonathan Wade, Jr., died. The house was given Georgian styling in the mid-18th century, and was owned for many years in the 19th century by Samuel C. Lawrence, Medford's first mayor.The house was listed on the National Register of Historic Places in 1975.

The Henry Bradlee Junior House is located in Medford, Massachusetts. It was designed in the Queen Anne style by Peabody & Stearns circa 1881–1882. This was one of three houses built by the Halls and the Bradlees on their estate. This home was built for Henry Bradlee Junior, his wife Maude (Abbot) Bradlee and their son, Edward who was born in Boston in 1880. Henry and Maude were married on January 21, 1879 and this house was in part a wedding gift to them. They were married by Rev Leighton Parks in Boston, Massachusetts. The other two houses were built in the mid to late 1850s for Dudley C. Hall and for Henry Bradlee Sr. and his wife Hepsa Hall Bradlee. Of those homes, according to a survey by the Massachusetts Historical Commission, the Henry Bradlee Junior House is the best preserved. The MHC report states in part: Its many porches, turned posts, balconies, porte-cochere and chimney with divided flues (to allow space for a window to be placed in the center of its base) are the best details of their type in Medford. Mentioned in a deed of 1882, the house was probably constructed between March 1881 when the one and three-quarter acre [7,100 m3] parcel on which it stood was first surveyed, and April 1882, when Dudley Bradlee granted a mortgage on the property to Henry Bradlee and his wife, Maude. The only major alteration to the house has been the replacement of its original decorative shingle work with stucco. This change was probably made around 1910 when the area was being built up with fashionable Stucco Style houses. Henry Bradlee Junior came from an upper-class family from the Medford and Boston area. He was born January 30, 1851, and died April 13, 1894. His grandfather, Josiah Bradlee of Boston is known to have participated in the event known as the Boston Tea Party in 1773. He was a descendant of Governor Simon Bradstreet of the Massachusetts Bay Colony, as well as of Charles Tufts. Henry Bradlee Jr. had two siblings, Ellen Marion Bradlee and Dudley Hall Bradlee.

The Unitarian Universalist Church of Medford and The Osgood House are a historic Unitarian Universalist church building and parsonage house at 141 and 147 High Street in Medford, Massachusetts.

The Joseph K. Manning House is a historic house in Medford, Massachusetts. Built in 1875, this three story wood-frame house is the most elaborate Second Empire house in the city. The most prominent feature of this architecturally complex building is a hexagonal pavilion attached to its porch at the western corner. It has an elaborate jigsaw-cut frieze and Stick style decorative woodwork, with a balustrade with heavy turned balusters. The house's mansard roof is shingled in multiple bands of colored slate, and pierced by pedimented dormers. At the upper roof line there is iron cresting. The house was built for Joseph King Manning, the son of a wealthy lumber dealer.The house was listed on the National Register of Historic Places in 1989.

The US Post Office–Medford Main is a historic post office at 20 Forest Street in Medford, Massachusetts. Built in 1937, it is a fine example of construction work funded by the Public Works Administration, a jobs program of the 1930s. It was listed on the National Register of Historic Places in 1986.

The Bigelow Block is a historic commercial and residential building at the corner of Forest and Salem Streets in Medford, Massachusetts. The Victorian block was built in 1886 for the locally prominent Bigelow family; it is a four-story brick building with sandstone trim, terra cotta plaques, and copper-clad turret at the corner. It occupies a prominent position in the center of Medford, and is one of few surviving 19th century commercial buildings in the city.The building was listed on the National Register of Historic Places in 1975.

The Old Medford High School is a historic high school building at 48–64 Forest Street in Medford, Massachusetts. The building presently houses condominiums and a community theater. It was built in 1894–1896 and added to the National Register of Historic Places in 1983.In 1914, an addition was added to the building, nearly doubling it in size, due to the growth of Medford. In 1929 the north wing was constructed, followed by the south wing ten years later. In 1984, the city sold the building to a property developer to convert it into condominiums.

The Grace Episcopal Church is an Episcopal church designed by noted American architect H. H. Richardson, with a major stained glass window by John LaFarge. It is located at 160 High Street, Medford, Massachusetts and now listed on the National Register of Historic Places. The church was constructed 1867-1869. It is one of Richardson's earliest works and the second of his churches (now the earliest remaining since his Unity Church, Springfield, has been demolished). Its cornerstone was laid in 1867 but by August 1868 it was evident that construction costs would exceed the budget. After the Brooks family covered the remaining construction costs, it became a private chapel under Episcopal law. In 1873 the family delivered the church to the parish, and it then was consecrated by the Bishop of Maine. The church is designed in a picturesque Gothic style with 90-foot (27 m) high steeple (square base, octagonal spire), asymmetrical massing, and rough-cut walls of glacial boulder with granite trim. A massive slate roof, in gray with bands of red slate, dominates the nave's low walls and the five-sided apse attached to its east wall. The church has undergone extensive modifications from its original design. In 1882 a Sunday school annex was appended, in 1883 the nave interior was redecorated, and in 1957 further additions were made. In 1962 the chancel was reworked and Richardson's original altar given to the Brooklyn Museum. In the early 1970s Richardson's dark-stained interior was replaced by a brighter woodwork. As of 2007 only the pulpit remains of his original interior. LaFarge's window, "Rebecca at the Well", forms the center of the nave's south wall, and was probably installed in 1884 or 1885.