Otis-Wyman House

Winter Hill is a neighborhood in Somerville, Massachusetts. It gets its name from the 120-foot hill that occupies its landscape, the name of which dates back to the 18th century. Winter Hill is located roughly north of Medford Street, west of McGrath Highway, and east of Magoun Square.

The house at 21 Dartmouth Street in Somerville, Massachusetts is a well preserved Queen Anne style house. The 2.5-story wood-frame house was built c. 1890, possibly for Rufus Stickney, one of the developers of the area during that time. Its most distinctive feature is the front gable end, which contains a projecting box with a pair of windows, supported by brackets and topped by an entablature. The upper floors also include bands of decoratively cut shingles.The house was listed on the National Register of Historic Places in 1989.

The H. Warren House is a historic house in Somerville, Massachusetts. The two story wood-frame house was built c. 1870, probably by J. K. Moore, a local cabinet maker. It is one of the finest Second Empire structures in the Winter Hill area of the city. The mansard roof is pierced by numerous gabled and pedimented dormers, the cornice is lined with dentil molding and studded with brackets, and the house corners have quoins designed to resemble stonework.The house was listed on the National Register of Historic Places in 1989.

The Elisha Hopkins House is a historic house in Somerville, Massachusetts. The 2.5-story wood-frame house was built c. 1868 by Elisha Hopkins, a ship's master. It has a typical period Italianate plan, with three bays across and small center gable. The gables have oculi windows characteristic of the style, and there is a later Colonial Revival front porch with turned posts and brackets, and a gable over the entry stair.The house was listed on the National Register of Historic Places in 1989.

Langmaid Terrace is a historic apartment complex at 359—365 Broadway in the Winter Hill neighborhood of Somerville, Massachusetts. The architecturally eclectic brick building was built in 1891 by the heirs of Samuel P. Langmaid, a local landowner. The Langmaid family was also responsible for the Langmaid Building on Highland Avenue. The architect was J. Pickering Putnam of Boston. The building is Queen Anne in inspiration with multiple roof lines, gables, and towers of varying heights and styles. Dormers project from the mansard roof, faced with stepped brick.The building was listed on the National Register of Historic Places in 1989.Since 2009, the end unit at 365 Broadway has received notice as the residence of Barack Obama from 1988 to 1991 while he attended Harvard Law School.In 2021, a granite marker commemorating Obama's residency was placed in the front garden area, deemed the President Obama Rose Garden At Winter Hill, MA.

The Peter and Oliver Tufts House (also known as the Peter Tufts House) is a historic house in Somerville, Massachusetts. Built about 1714, it is one of the oldest houses in the city's Winter Hill neighborhood, and was owned in the 19th century by members of the Tufts family responsible for developing the city's brickyards. The building was added to the National Register of Historic Places in 1989.

The Charles Adams-Woodbury Locke House is an historic house in Somerville, Massachusetts. The Greek Revival house was built about 1840 for a Boston leather merchant and was one of the first residences of a commuter, rather than a farmer, in the Winter Hill neighborhood of the city. The house was listed on the National Register of Historic Places in 1989.

The Downer Rowhouses are two sets of Second Empire row houses that are back to back at 55 Adams Street and 192-200 Central Street, Somerville, Massachusetts. Built c. 1880, they are among the first buildings of their type built in the city. The two groups were separately listed on the National Register of Historic Places on September 18, 1989, as Downer Rowhouses (Central Street) and Downer Rowhouses (Adams Street).

The Susan Russell House is a historic house in Somerville, Massachusetts. The 1.5-story Greek Revival cottage is estimated to have been built in the 1830s, based on a stylistic analysis. It is a rare survivor of a style that was once common in Somerville. Greek Revival element is its door surround. The house was added to the National Register of Historic Places in 1989.The land on which the Susan Russell House sits was purchased from Oliver Tufts in the early 19th century.

The Broadway Winter Hill Congregational Church is a historic church building at 404 Broadway in Somerville, Massachusetts. Built in 1890–91 to a design by Hartwell and Richardson for a Congregationalist congregation founded in 1865, it is one of the city's only examples of Shingle style architecture, and one of its finer architect-designed buildings from the 19th century. The building was listed on the National Register of Historic Places in 1989. It is now home to the Vida Real Church.

Gilman Square is a neighborhood in the area around Central Hill in Somerville, Massachusetts. Historic Gilman Square is at the junction of Medford, Pearl, and Marshall streets and has been a small commercial center since the mid 19th-century but with the development of the Gilman Square Green Line station, city planning documents consider the area within a rough ten-minute walk of the new station to be part of the Gilman Square neighborhood. Neighborhood lines are fuzzy and Gilman Square is sometimes considered part of the extensive Winter Hill neighborhood. The area has also been referred to as Central Hill, and distinct from Winter Hill to the north, Spring Hill to the southwest, and Prospect Hill to the southeast.

Gilman Square station is an under-construction light rail station on the Massachusetts Bay Transportation Authority (MBTA) Green Line located at Gilman Square in Somerville, Massachusetts. The accessible station has a single island platform serving the two tracks of the Medford Branch, which parallels the Lowell Line. It is planned to open in mid-2022 as part of the Green Line Extension (GLX) and will be served by the E branch. The Boston and Lowell Railroad (B&L) opened a station at Winter Hill in 1863; it was rebuilt in 1886–1888. The station was served by the Boston and Maine Railroad, successor to the B&L, until around 1930. Extensions to the Green Line were proposed throughout the 20th century, most with Winter Hill as one of the intermediate stations. A Gilman Square station at the Winter Hill site was officially chosen for the GLX in 2008. Cost increases triggered a wholesale reevaluation of the GLX project in 2015, and a scaled-down station design was released in 2016. A design and construction contract was issued in 2017. Construction of Gilman Square station began in early 2020 and was largely completed by late 2021.