Building at 25–27 River Street

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.

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.

The William E. Alden House is a historic house at 428 Hamilton Street in Southbridge, Massachusetts. Built in 1882 for a prominent local businessman, it is a fine example of a modest home with Queen Anne and Stick style decoration. It was listed on the National Register of Historic Places in 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.

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 Holy Trinity Episcopal Church, formerly the Evangelical Free Church, is a historic church building at 446 Hamilton Street in Southbridge, Massachusetts. Built in 1869 for a nominally non-denominational congregation of senior Hamilton Woolen Company employees, it has house an Episcopal congregation since 1921. The building is architecturally noted for its Romanesque and Gothic Revival features, and was listed on the National Register of Historic Places in 1989.

The Cliff Cottage is a historic cottage at 187 Mill Street (at its corner with Cliff Street) in Southbridge, Massachusetts. Built before 1855, it is a distinctive combination of Greek Revival and Gothic features executed in stone. It was listed on the National Register of Historic Places in 1989.

The Academie Brochu is a historic school at 29 Pine Street in Southbridge, Massachusetts. Built in 1899, it is one of the city's most imposing Colonial Revival buildings, and a significant element of the development of its Franco-American community. The building was listed on the National Register of Historic Places on June 22, 1989. It was gifted to Harrington Memorial Hospital and now houses Harrington Health System offices.

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.

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

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 Chamberlain-Bordeau House is a historic house at 718 Main Street in Southbridge, Massachusetts. Built sometime between 1855 and 1870, it is one of the best preserved Italianate houses in the city. It was listed on the National Register of Historic Places in 1989.