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The E. B. Cummings House is a historic house at 52 Marcy Street in Southbridge, Massachusetts. Built in the 1870s, it is an unusually late example of Greek Revival architecture with Italianate embellishments and later Victorian additions. The house was listed on the National Register of Historic Places on June 22, 1989.

St. Peter's Roman Catholic Church—St. Mary's School was a historic church and school building at Hamilton and Pine Streets in Southbridge, Massachusetts. Built in 1853, it was the first Roman Catholic church located in south-central Massachusetts, and one of only two Greek Revival church buildings in the city. Later used as a school and parish hall, it was destroyed by fire in December 1999. The building was listed on the National Register of Historic Places in 1989.

The A. Kinney House is a historic house located in Southbridge, Massachusetts.

The Mary E. Wells School is a historic school building at 80 Marcy Street in Southbridge, Massachusetts. Built in 1916, it is one the last known commissions of the architectural firm Peabody & Stearns. It was built with funding from Mary E. Wells, wife of George Wells, founder of the locally prominent American Optical Company. The building was listed on the National Register of Historic Places in 2023. The building was used as a school until 2012, and has since been converted into residences.

Trinity Catholic Academy is a private Roman Catholic school located on the grounds of St. Mary's Church in Southbridge, Massachusetts. It is located in the Roman Catholic Diocese of Worcester.The school has an approximate enrollment of 250 students and classes range from Pre-K to the 8th grade. The student body is predominantly Catholic, but the Academy does accept students of all faiths. The school official Facebook page is:https://www.facebook.com/TCABobcats/

The Alexis Boyer House is a historic house at 306 Hamilton Street in Southbridge, Massachusetts. Built in 1888, it is a good local example of Queen Anne/Stick style architecture. It was built for Alexis Boyer, a political leader in the city's sizable French Canadian community. The house was listed on the National Register of Historic Places in 1989.

Notre Dame Catholic Church is a historic church in Southbridge, Massachusetts. It is one of two churches serving the Parish of Saint John Paul II; Saint Mary Church, located at the corner of Marcy and Hamilton Street, also serves as the location of the Parish Center and Rectory. Notre Dame was built from 1912 to 1916 and added to the National Register of Historic Places in 1989.

The J. M. Cheney Rental House is a historic house at 32 Edwards Street in Southbridge, Massachusetts. It is a well-preserved vernacular Victorian house exhibiting details in a number of different styles. It was built in the late 19th century, during a second phase of construction in the Hamilton Street area that replaced larger properties of wealthier owners with smaller, more densely site, middle-class housing. This house was built for J. M. Cheney, treasurer of the Litchfield Shuttle Company, who owned several properties in the area, including the adjacent Kinney House, and also lived nearby. There is no hard evidence the property was intended for use as a rental, but this seems likely.The basic house layout, a three-wide side-hall plan, was typical of the period, but the house's ornamentation is not. The window caps and the rounded gable window are Italianate in styling, but there is also a steeply pointed Gothic-style gable dormer, and the gable ends are decorated with Stick style ornaments. The front porch exhibits both Italianate and Queen Anne styling, with turned posts, brackets, and a decorative rectangular patterned balustrade.The house was listed on the National Register of Historic Places in 1989.

The J. J. Oakes House is a historic house at 14 South Street in Southbridge, Massachusetts. It is one of a few surviving Second Empire houses in Southbridge. The two story wood-frame house was built sometime before 1870 for James Jacob Oakes, who grew up nearby, and owned a dry goods and clothing store in town. The house was later acquired by J. J. Delahanty, who owned a furniture store in the Alden-Delahanty Block in Globe Village. Although it is predominantly Second Empire in its styling (as indicated by the concave slate mansard roof), it also has significant Italianate detailing, including the three bay facade and bracketed eaves.The house was listed on the National Register of Historic Places in 1989.

Beechwood is a historic house at 495 Main Street in Southbridge, Massachusetts. Built in 1868, it is prominent locally as a fine early example of Stick style architecture, and as one of the first houses to be built that became one of the city's upper-class neighborhoods. It was listed on the National Register of Historic Places in 1989.

The Chapin Block is a historic commercial building at 208-222 Hamilton Street in Southbridge, Massachusetts. Built in 1888, it is the only Shingle style commercial building in Southbridge. It was listed on the National Register of Historic Places in 1989.

The Building at 29–31 River Street in Southbridge, Massachusetts, is one of two once similar triple-deckers built during a housing boom related to the success of the nearby Hamilton Woolen Company. Of six such houses built in the 1910s and 1920s on River Street, only it and 25-27 River Street remain. The building was listed on the National Register of Historic Places in 1989, since when its historic integrity has been compromised.