Winchester High School (Massachusetts)

St. Mary's Catholic Church is a historic church at 159 Washington Street in Winchester, Massachusetts. The church is part of St Mary's Parish, which includes St Mary's School. Both are part of Roman Catholic Archdiocese of Boston.

The Winchester Savings Bank is a bank headquartered at 661 Main Street in Winchester, Massachusetts. The bank is an independent, mutual, state-chartered institution with a mission of meeting the financial needs of the communities which it serves. The bank is directed by a board of trustees elected by the bank's corporators, a group of civic-minded, local individuals. Since the Bank is mutual, all profits from operations are reinvested in the bank.

The George Brine House is a historic house in Winchester, Massachusetts. Built about 1865, it is a well-preserved example of Second Empire architecture. It was listed on the National Register of Historic Places in 1989.

Winchester Town Hall is a historic town hall at 71 Mount Vernon Street in Winchester, Massachusetts. The 2+1⁄2-story brick building was built in 1887 to a design by Rand and Taylor. It was funded in part by a bequest from William Parsons Winchester, for whom the town is named. Stylistically the building has Queen Anne and Romanesque Revival styling. Its most prominent feature is the clock tower, a four-plus story square tower topped by a pointed roof with gables.The building was listed on the National Register of Historic Places in 1983, and included in the Winchester Center Historic District in 1986.

The Edward Sullivan House is a historic house in Winchester, Massachusetts. This small, 1+1⁄2 story house was built around 1875, and is the best-preserved example of a 19th-century worker's cottage in the town. It is three bays wide, with a side-gable roof, and simple vernacular Italianate styling. It has almost no exterior architectural styling, except for a transom window and modest entablature over the front door. The house is one of five owned by Edward Sullivan, a stonemason, and is located near St. Mary's Catholic Church, an area where many Irish immigrants sought to settle.The house was listed on the National Register of Historic Places in 1989.

The O. W. Gardner House is a historic house in Winchester, Massachusetts. The 1+1⁄2-story wood-frame house was built c. 1840 by Oliver W. Gardner, and was originally one of a pair built in the area (the other is no longer extant). It is one of Winchester's finest examples of Gothic Revival architecture, with elaborate scroll-sawn vergeboard in its steep gables, which also occurs in miniature on the gable-roofed portico that shelters the door. It has windows topped by label mouldings, and some windows are topped by a Gothic pointed-arch. The corner boards have elaborately grooved pilasters.The house was listed on the National Register of Historic Places in 1989.

The Pressey-Eustis House is a historic house in Winchester, Massachusetts. The 1+1⁄2-story wood-frame house was built in the early 1850s, and is a fine local example of Gothic Victorian decoration. It has an L-shaped layout typical of the period, with a porch at the crook of the L. Its most distinctive features are the vergeboard featuring an unusual acorn pattern, and the finials at the gable tops. George Eustis, town treasurer 1910–24, lived here from c. 1870 to 1940.The house was listed on the National Register of Historic Places in 1989.

The S. B. White House is a historic house in Winchester, Massachusetts. The 1+1⁄2-story wood-frame house was built in the early 1850s, and is one of the finest local examples of Gothic Revival architecture. Its exterior is finished in clapboards, and its steeply-pitched gables are decorated with icicle-like vergeboard. Its entry is flanked by sidelight windows and sheltered by porch added later. The house was built and owned by Samuel B. White, Jr., who served as Winchester's first town treasurer.The house was listed on the National Register of Historic Places in 1989.

The Amy B. Mitchell House is a historic house at 237 Highland Avenue in Winchester, Massachusetts. The 2+1⁄2-story wood-frame house was built c. 1909 in an area made fashionable after the establishment of the Middlesex Fells Reservation, and is an excellent local example of Medieval Revival styling. It features jerkin-headed cross gable sections decorated with vertical valances, exposed rafter ends, and a rustic fieldstone chimney.The house was added to the National Register of Historic Places in 1989.

The Winchester Center Historic District encompasses the commercial and civic heart of Winchester, Massachusetts. It is roughly bounded Mt. Vernon and Washington Streets, Waterfield Road, Church and Main Streets. The district includes a number of Romanesque Revival buildings, including Winchester Town Hall and the Winchester Savings Bank building on Mount Vernon Street. Noted architects who contributed to the district include Robert Coit and Asa Fletcher. The district was listed on the National Register of Historic Places in 1986.

The James H. Mann House is a historic house at 23 Hancock Street in Winchester, Massachusetts. The 2+1⁄2-story wood-frame house was built by James H. Mann for his own use. Mann was a prominent local builder who also built the Carr-Jeeves House, another picturesque house with a mixture of architectural elements. This house is predominantly Gothic Revival in character, with its main body topped by a double roof roughly looking like a monitor. There is a three-story tower topped by a jerkin-headed roof, whose gable lines are decorated by Stick-style vergeboard.The house was listed on the National Register of Historic Places in 1989.

Winchester is a town in Middlesex County, Massachusetts, located 8.2 miles (13.2 km) north of downtown Boston as part of the Greater Boston metropolitan area. It is also one of the wealthiest municipalities in Massachusetts. The population was 22,970 at the 2020 United States Census.