Deacon William Leland House

The Bullard Memorial Farm is a historic farm located at 7 Bullard Lane in Holliston, Massachusetts. It was first settled by Benjamin Bullard in approximately 1652. The land was purchased from local Native Americans. Bullards farmed the land until 1916, when John Anson Bullard bequeathed it to the Bullard Memorial Farm Association (“BMFA”), which had been created in 1909. The main house was built in 1777 and enlarged in 1794; the property has a number of outbuildings, including a barn, a vinegar building, a cider building, a blacksmith shop, a library, a locker building, a small shed/horse barn, and a cottage. The farm includes 100 acres (40 ha) under a forestry and agricultural designation and another 50 acres (20 ha) are undeveloped pasture." The farm was listed on the National Register of Historic Places in 1995.

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.

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 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.

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 Sewall–Ware House was a historic house at 100 S. Main Street in Sherborn, Massachusetts. The house stood on land once belonging to Massachusetts judge Samuel Sewall (best known for his participation in the Salem witch trials). The house may have been constructed by Sewall's instructions for a tenant farmer. In the mid-18th century it was the boyhood home of Harvard College divinity professor Henry Ware, and remained in the Ware family well into the 19th century. It was added to the National Register of Historic Places in 1986. The house no longer stands at the location described in the listing papers, and has probably been demolished.

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 Asa Sanger House is a historic house in Sherborn, Massachusetts. The oldest portion of this 2+1⁄2-story timber-frame house is, based on architectural evidence, believed to date to the early decades of the 18th century. It has transitional styling, including features of First Period and later Georgian styling. At the time of the American Revolutionary War the house was owned by Asa Sanger, whose family was prominent in town civic and economic affairs.The house was listed on the National Register of Historic Places in 1986.

The Richard Sanger III House is a historic house in Sherborn, Massachusetts. It is a 2+1⁄2-story timber-frame house, five bays wide, with a side gambrel roof and clapboard siding. The windows of the front facade are symmetrically placed, but the door is slightly off-center, flanked by sidelight windows and topped by a gabled pediment. The house was built c. 1734, with a rear leanto added around 1775. It is unusual in the town as an 18th-century gambrel-roofed house with leanto. Sanger was the son of a Boston merchant, and one of the few people on the town documented to own slaves.The house was listed on the National Register of Historic Places in 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.

The Clark–Northrup House is a historic house in Sherborn, Massachusetts. Built c. 1845–55, it is a locally unusual example of a Greek Revival house with a more traditional Georgian side-gable roof. The house was listed on the National Register of Historic Places in 1986.