Building at 38–42 Worcester Street

The Sacred Heart Church Historic District encompasses the complex of buildings associated with the Sacred Heart Church on Charlton Street in Southbridge, Massachusetts. The complex, which was listed on the National Register of Historic Places in 1989, is the second Roman Catholic parish (after Notre Dame) built to serve Southbridge's growing Franco-American population. The four buildings in the complex were built between 1909 and 1926 in the Colonial Revival style.The parish was formally established in 1908, and construction on its buildings began in 1909. The first two to be built were the rectory and convent. The rectory, at 40 Charlton Street, is a 2+1⁄2-story brick structure with a hipped roof which is pierced by a few gable dormers. Its front facade features a central rounded bay, and both side facades have projecting rectangular bays. The convent is of similar styling, except its front facade features two side rounded bays and a central porch. Its rear facade also features an entry porch.The school, which opened in 1910, was at first run by the Sisters of Nicolette, who also ran the Notre Dame parish school. The building is a large two-story brick block, with projecting sections at the center of each side that rise up to the roof line on three sides, and above the main roof line on the front, which features three round Roman arched doorways. The main roof his hipped, as are the roof lines of the projecting sections.The church was not completed until 1926. Unlike the other buildings, it has a marked Gothic character, with Gothic-style arched windows, buttresses, and Gothic ornamental detailing.

The George Sumner House is a historic house at 32 Paige Hill Road in Southbridge, Massachusetts. The 2+1⁄2-story late Federal wood-frame house was built sometime before 1830, probably for Major George Sumner (who is recorded as its owner in 1855). Sumner was a leader in the early development of the textile industry in Southbridge, being the first in the area to offer as a service the complete cycle of woolen textile processing, although some work was still initially done in homes, not in a factory setting. The house is notable for the fanlight window on the gable end, which is a late 19th-century addition.The house was listed on the National Register of Historic Places in 1989.

St. George's Greek Orthodox Church is a historic Greek Orthodox Church building at 55 North Street in Southbridge, Massachusetts. Built in 1932, it is the oldest Orthodox church in the city, and is a locally rare example of Byzantine and Greek architecture. The church was listed on the National Register of Historic Places in 1989.

The Twinehurst American Optical Company Neighborhood is a residential historic district in Southbridge, Massachusetts. It consists of seven three family houses built by the owners of the American Optical Company to provide housing for their workers. The district was listed on the National Register of Historic Places in 1989.Six of the seven houses are on Twinehurst Place, a short loop near the junction of Paige Hill Road and Central Street; one house has an address on Central Street but is physically adjacent to the others. The center of the loop is an open grassy area, giving a clear view of the neighborhood. All of the houses were built between 1915 and 1917, and exhibit Colonial Revival characteristics despite subsequent alteration. The typical house has a three-bay front facade, with the building entrances in the end bays, topped by a gabled pediment above. Two of the buildings have only a single entrance. Most of the buildings have three-part picture windows in the center bay.The houses appear to be somewhat typical 2+1⁄2-story two-family houses, with their gables toward the street. However, each has extended dormers sufficient to provide a full apartment on the third floor. Each unit originally had a porch on the south side, but in all cases these have been subsequently enclosed. The houses originally had wood-shingle siding, but this has generally been changed: on some of the houses it has been replaced by wider wood siding, and on others by synthetic siding. Despite these changes, Colonial Revival trim details have generally been preserved.

The Central Mills Historic District encompasses a historic mill complex on the Quinebaug River in central Southbridge, Massachusetts. Located at the corner of Foster and North Streets, the site consists of three brick buildings, the oldest of which has portions dating to 1837. Despite being extensively rebuilt in the early 20th century, the complex has an appearance that is more typical of 19th century mills.The Central Manufacturing Company was established in 1837, and was one of Southbridge's major employers well into the 20th century. The company built its premises on the site of Southbridge's earliest grist- and sawmills, and the town grew around the facility. By late in the 19th century most New England textile mills were in decline, due to increased competition in the South. However, Central Manufacturing embarked on a major renovation of its plant in 1908. It knocked a significant portion of the 1837 plant, and built the present two story brick structure, with the surviving 1837 section attached to its rear. The building is in the Romanesque Revival style, with rounded arch windows and a small tower.In addition to the main factory building, there are two other buildings in the complex. One is a small single story office building, also built in 1908 and with Romanesque Revival styling. This building is on the same parcel as the main building. The third building is a more utilitarian brick warehouse, built 1915, which is located across North Street (but also fronting on Foster) from the main building.The district was listed on the National Register of Historic Places in 1989.

The Windsor Court Historic District is a residential historic district in Southbridge, Massachusetts, United States. It is a collection of five three-family residences located on Windsor Court and adjacent North Street that were built by the American Optical Company between 1915 and 1917 to provide worker housing. The district was listed on the National Register of Historic Places in 1989.

The House at 3 Dean Street in Southbridge, Massachusetts is a rare well-preserved example of a worker housing cottage built by the locally important American Optical Company. It is a small 1+1⁄2-story house, three bays wide, presenting its side to the street. At the time of its listing on the National Register of Historic Places in 1989, it still had the original siding from its original construction, about 100 years earlier, which included cut shingles in the gable, and bracketed eaves. These details have since been lost or obscured by the application of modern siding (see photo).

The House at 34 Benefit Street in Southbridge, Massachusetts is a modest factory worker's cottage built by the American Optical Company during a period of its expansion in the 1870s. After opening its new Main Plant in The Flats section of Southbridge, workers began to migrate there from the Globe Village neighborhood, increasing demand for housing in that area. It is a narrow 1+1⁄2-story wood-frame structure, which has some architectural style despite its simplicity. The styling is basically Italianate in influence, with wide eaves, and a porch with decorative posts, balustrade, and brackets.The house was listed on the National Register of Historic Places in 1989.

Southbridge station is a former train station in Southbridge, Massachusetts. Built in 1910 by the New York, New Haven and Hartford Railroad (NYNH&H), it is a rare local example of Spanish Mediterranean architecture, and is the only surviving railroad building in the town. The building was listed on the National Register of Historic Places in 1989 as New York, New Haven & Hartford Passenger Depot. It presently serves as the town's registry for motor vehicles.

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.

The house at 59–63 Crystal Street in Southbridge, Massachusetts is a well-preserved multiunit residential structure built to provide worker housing for the American Optical Company around the turn of the 20th century. It is a 2.5-story wood-frame house, in a late Victorian style with both Italianate and Colonial Revival elements. Its side hall, gable front appearance is typical of many late 19th century houses in Southbridge.The house was listed on the National Register of Historic Places in 1989.

The Comins-Wall House is a historic house located at 42 Hamilton Street in Southbridge, Massachusetts. Built about 1850, it is a distinctive local example of a Greek Revival cottage with later Victorian embellishments. It was listed on the National Register of Historic Places on June 22, 1989.