Chapin Block

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

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/

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 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 George H. Hartwell House is a historic house at 105 Hamilton Street in Southbridge, Massachusetts. It is a rare example of a modest vernacular Italianate house in Southbridge, and one of the only ones built of brick. It was built in the 1850s, not long after that stretch of Hamilton Street was laid out, for Dr. George Hartwell, nephew of Dr. Samuel Hartwell. The Hartwells controlled the Hartwell Block on Main Street, and George Hartwell ran a pharmacy, which continued in business into the 1970s. While the house has significant Italianate features such as bracketed eaves and paired windows, it lacks the flat roof line that is characteristic of other local Italianate houses, and is less massive than the more imposing James Gleason House and Chamberlain-Bordeau House.The house 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.

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 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 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.

The Theodore Harrington House is a historic house at 77 Hamilton Street in Southbridge, Massachusetts.

The Dunbar-Vinton House is a historic house at Hook and Hamilton Streets in Southbridge, Massachusetts, USA. Probably built in the early 19th century, it is locally unusual for its brick construction at that time, and may have been built as a district schoolhouse. It was listed on the National Register of Historic Places in 1989.