Simon Plimpton Farmhouse

The Judson–Litchfield House is a historic house at 313 South Street in Southbridge, Massachusetts. Built sometime in the 1830s, it is a well-preserved local example of brick Greek Revival architecture, of which there are few surviving examples in the city. The house was listed on the National Register of Historic Places in 1989.

The Westville Dam is located on the Quinebaug River between Southbridge and Sturbridge, about 1.3 miles (2.1 km) west of the Southbridge town center and 18 miles (29 km) southwest of Worcester, Massachusetts. Designed and constructed by the United States Army Corps of Engineers, this dam substantially reduces flooding along the Quinebaug and Thames rivers. Construction of the project began in June 1960 with completion in August 1962 at a cost of US$5.6 million. The Westville reservoir is located within the Quinebaug River Watershed and is part of the Thames River Basin. Access to the site is available from Interstate 84 and State Route 131.

The Napoleon LaRochelle Two-Family House is a historic house at 30 Pine Street in Southbridge, Massachusetts. An excellent example of a vernacular Victorian duplex, it was probably built around 1890 for Napoleon LaRochelle, a polisher for the American Optical Company. He owned this and another house next door which was built in the same style. Its plan is a typical front-gable side entry layout, this time with a central cross gable. It has some bargeboard decoration on the front gable, and its front porch features a basket-weave railing.It was built in 1890 and added to the National Register of Historic Places in 1989.

The H. Morse House is a historic house at 230 South Street in Southbridge, Massachusetts. The 2+1⁄2-story wood-frame house was probably built in the 1840s, and is a well-preserved example of a rural Greek Revival farmhouse. It was shown on an 1855 map as being owned by H. Morse, in the 1870s by Lyman Morse, and in 1878 by "Misses Morse". The house has some excellent Greek Revival features, including pilastered corner borders and an ornately decorated front door surround. A two-story addition was made to the side of the house in the 1870s, and another was made to the rear in the 20th century.The house was listed on the National Register of Historic Places in 1989.

The Glover Street Historic District is a residential historic district in Southbridge, Massachusetts. The district encompasses a cluster of nineteen houses on or adjacent to Glover Street between High and Poplar Streets. The area was fully developed beginning in the first decades of the 20th century, filling in a previous round of development that had taken place in the 1890s. These houses were targeted at Southbridge's growing middle class.The land on which Glover Street was laid out was originally part of the Clarke-Glover Farm. In the 1880s a series of Gothic style 1+1⁄2-story cottages were built at the northern end of Glover Street. Six of these in particular feature jigsaw-cut bargeboard trim decoration and are among the best preserved of their type in Southbridge. This period of development also saw construction of a house and barn with Italianate Victorian styling.The second construction phase ran from the 1910s to the 1930s, and once again saw the construction of modestly sized houses in the styles of the period. Most of these structures are Colonial Revival in styling, although there is one house with some Bungalow/craftsman styling. The district includes one house that predates the development of Glover Street: a vernacular frame house dating to the early 19th century that faces High Street at its corner with Glover. That house may have been associated with the Clarkes whose land it was.The district was listed on the National Register of Historic Places in 1989.

The Lorenzo R. Stone House is a historic house at 218 South Street in Southbridge, Massachusetts. It was built between 1830 and 1855 for Lorenzo Stone, occupation unknown. Other houses were built in this area during the same time period due to the expansion of the Globe Village area, and were occupied to middle class workers and supervisors of the Hamilton Woolen Company. This is a 2+1⁄2-story wood-frame house, with a simple three-bay side-hall configuration. The exterior features fine Greek Revival detailing, including corner pilasters and a pedimented gable with frieze trim. The house is not out of scale with the modest houses that surround it.The house was listed on the National Register of Historic Places in 1989.

The Albert H. Wheeler House is a historic house at 219 South Street in Southbridge, Massachusetts. It was built in the late 19th century, and is an example of a modest Queen Anne Victorian. Its owner, Albert H. Wheeler, was a Civil War veteran and dry goods merchant with a shop in the Globe Village neighborhood. Wheeler died in the 1910s, and his widow lived in the house until at least 1928. It was eventually acquired by the American Optical Company and used for company housing.The house follows a simple L-shaped plan, with a front porch in the crook of the L that was added in the 20th century. The house was added to the National Register of Historic Places in 1989.

The Clarke–Glover Farmhouse is a historic house at 201 South Street in Southbridge, Massachusetts. Built about 1830, it is a good local example of Greek Revival architecture. It was listed on the National Register of Historic Places in 1989.

The High–School Streets Historic District encompasses a cluster of fourteen houses representing one of the best well preserved mid-19th century residential districts in Southbridge, Massachusetts. Located in the city's Globe Village area, the houses are predominantly Greek Revival in style. The district was listed on the National Register of Historic Places in 1989.

The Hamilton Mill—West Street Factory Housing is a historic house at 45 West Street in Southbridge, Massachusetts. Built in the second quarter of the 19th century, it was a particularly architecturally elaborate example of a worker tenement house with Greek Revival elements, and was listed on the National Register of Historic Places in 1989 for its architecture. It has since been resided, losing most of those features.

The Globe Village Fire House is a historic former fire house on West Street at Main Street in Southbridge, Massachusetts. It is the first of two fire stations built by the city in the 1890s; the other, the Elm Street Fire House, is still in use as a fire station. The building was listed on the National Register of Historic Places in 1989. At the time of its listing it had been repurposed for use by a veterans group.

The Hamilton Mill Brick House is a historic house at 16 High Street in Southbridge, Massachusetts. Built c. 1855 by the Hamilton Woolen Mill Company, it is one of a small number of brick company housing units to survive from that time. The house was listed on the National Register of Historic Places on June 22, 1989.