Bullard Farm

The Deacon William Leland House is a historic house in Sherborn, Massachusetts. It is a 2+1⁄2-story main dwelling, five bays wide, with a small ell to the west. It has a side gable roof with central chimney, and relatively simple trim. The house was built in 1717 for Deacon William Leland, son of one of the area's first settlers, and has seen relatively little exterior alteration, unlike other early houses in the town.The house was listed on the National Register of Historic Places in 1986.

The H. G. Vaughn House is a historic summer estate house at 5 Sparhawk Road in Sherborn, Massachusetts.

The Addington Gardner House is a historic First Period house in Sherborn, Massachusetts. Its oldest portions dating to about 1730, it is one of the community's oldest surviving buildings, and a good example of transitional First-Second Period style. The house was listed on the National Register of Historic Places in 1990.

The Woodland Farm–Leland House is a historic house in Sherborn, Massachusetts. The oldest portion of this house, a three-bay section with chimney, was built c. 1705 by Hopestill Leland, and enlarged by the addition of a leanto to the rear c. 1715. About 1760 it was widened to a full five bay width, and ells were added to either side c. 1820 and 1950. The exterior has exhibits a variety of styles, with Federal and Italianate elements. The house's original clapboards have been shingled over.The house was listed on the National Register of Historic Places in 1986.

Oak Grove Farm is a historic First Period farmstead in Millis, Massachusetts. The 2+1⁄2-story wood-frame farmhouse was probably built in three phases, the first of which was in the early 18th century. Around this time, the left five bays of the house were built, as was a central chimney. In the second quarter of the 19th century, three bays were added to the right, giving the building its current asymmetrical eight-bay facade. Finally, in 1884 a series of modifications and additions were made. The central chimney was removed, a leanto section was added to the rear of the house, and the front porch was added. A second porch was also built onto the rear ell around this time.The land on which the farmhouse stands has been farmed by English settlers since at least 1677, when Josiah Rockwood (also sometimes referred to as "Rockett") owned the property. Although maps show a house at the site in 1713, there is no other documentary evidence of the house until 1783, when a deed transferring the farm, with house, was recorded. For much of the 19th century the farm was owned by the Lovell family; it was purchased by Lansing Millis (the namesake of the town) in 1879. Millis, a railroad executive, established a dairy farm on the property, and gave it the name "Oak Grove Farm". His family used the property as a summer residence until 1883, after which he converted the house into a boarding house for the farm workers. By 1893 (after Millis' death) the farm was reported to be the largest dairy farm in New England.In the 20th century the property changed hands a few times, but remained in use as a dairy farm. In 1984, with a sale planned to a developer, the town purchased the property as one of the last open spaces near the town center. The farmland has been converted for use as recreational facilities, and the house has been restored and is managed by the town as a rental property.The farm was listed on the National Register of Historic Places in 2011.

The Morse–Tay–Leland–Hawes House is a historic house in Sherborn, Massachusetts. The farmhouse was built about 1700 by James Morse (born 1686), and added to the National Register of Historic Places in 1986. It consists of a 2+1⁄2-story main house in 4 bays, with single story rear wing. Surface treatments are late Georgian in style, probably added by Dr. Jonathan Tay in the 1770s or 1780s, and include a semicircular fanlight and narrow Doric pilasters framing the front door.

The John Partridge House is a historic house in Millis, Massachusetts. It is a 2+1⁄2-story wood-frame house, five bays wide, with a side-gable roof, large central chimney, a front entry with Greek Revival surround. It was built in the second half of the 17th century (the exact date being disputed), and is among the oldest buildings in the town. John Partridge, Sr. or his son John, Jr. was its likely builder, the former having been granted the land in 1659.The house was listed on the National Register of Historic Places in 1974.

Prospect Hill Cemetery is a historic cemetery on Auburn Road in Millis, Massachusetts. Founded in 1714, it is the town's only cemetery. Covering more than 18 acres (7.3 ha), it has more than 2,800 burials. Among those buried in the cemetery are politician Christian Herter, who served as U.S. Secretary of State and Governor of Massachusetts, and two Medal of Honor recipients, Charles Church Roberts and William D. Newland. The cemetery was listed on the National Register of Historic Places in 2006 with the help of a short documentary film by a Millis High School Freshman Dustin Fresh.

The East Holliston Historic District encompasses an area of early colonial settlement and later development in Holliston, Massachusetts. The linear district extends along Washington Street (Massachusetts Route 16) between Old Locust Street and the northeast junction with Curve Street, and then the full length of Curve Street. The area includes some of Holliston's early settlements, including the site of its first meeting house, near Curve Street and Jarr Brook. In the late 18th and early 19th centuries Jarr Brook became a point of industrial development, leading to the construction of a number of Greek Revival houses. Significant construction ended in the district around 1870.The district was listed on the National Register of Historic Places in 2002.

Ware's Tavern is a historic tavern (now a private residence) in Sherborn, Massachusetts. The two story wood-frame structure was built c. 1780 by Benjamin Ware as a house for his family. It has a centered entry that is now sheltered by a Colonial Revival (early 20th century) surround. Ware's son Eleazer converted the building into a tavern; it was greatly enlarged with an ell to the rear c. 1840. The building ceased to be used as a tavern by 1889; an ell was removed sometime in the 19th century, and now stands at 109 S. Main Street.The tavern was listed on the National Register of Historic Places in 1986.

The Charles Holbrook House is a historic house in Sherborn, Massachusetts. Built c. 1870–75, this modest house is the town's finest example of Second Empire styling. It was built for Charles Albert Holbrook (1846-1899), whose family operated a large apple cider mill in town. The house was listed on the National Register of Historic Places on January 3, 1986.

The Joseph Twitchell House is a historic house in Sherborn, Massachusetts. It was built circa 1710, or possibly 1690, with a north wing dating from the early 1800s. It is one of a small number of houses in Sherborn that have elements that may date to the 17th century. It is a 2+1⁄2-story wood-frame saltbox house, 3 wide bays, with a massive central chimney, side-gable roof, and clapboard siding. Inside it is laid out as a central hall, one room on either side, and lean-to at the rear. The Georgian front door is flanked by Doric pilasters and topped by a multi-pane transom and entablature.The house was listed on the National Register of Historic Places in 1986.