Woodland Farm–Leland House

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 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 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.

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 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.

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

The Thomas Fleming House is a historic house located in Sherborn, Massachusetts.

Sherborn is a town in Middlesex County, Massachusetts, United States. Located in Boston's MetroWest region, is in area code 508 and has the ZIP code 01770. As of the 2020 U.S. Census, the town population was 4,401.Sherborn shares its highly ranked public school system with the town of Dover. In addition to Dover, Sherborn is bordered by the towns of Natick, Framingham, Ashland, Millis, Holliston, and Medfield.