Winchester Savings Bank

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 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.

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.

The US Post Office—Winchester Main is a historic post office at 48 Waterfield Road in Winchester, Massachusetts. The single-story Classical Revival brick building was built in 1927 and 1928 by John P. Curley for the United States Postal Service. The building features neo-Classical temple fronts on its three principal facades, with a more elaborate projecting instance on the long south-facing facade, where the main entrance is located. The cornice has a simple dentil moulding in limestone; the roof is flat, but there is a raised clerestory section in the center.The building was listed on the National Register of Historic Places in 1987, and included in the Winchester Center Historic District in 1986.

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.

Winchester Center station is a temporarily closed MBTA Commuter Rail station in Winchester, Massachusetts. The station, located on a viaduct in downtown Winchester, was closed effective January 8, 2021 due to structural deterioration. Prior to closure, it served all Lowell Line trains as well as a limited number of Haverhill Line trains which run via the Wildcat Branch. Winchester Center station was not accessible prior to the closure, but accessible high-level platforms are being added during renovations taking place from December 2021 to April 2024.

Winchester High School is a comprehensive 9–12 high school located in Winchester, Massachusetts, United States. Founded in 1850, it moved into its current location in the spring of 1972. Ranked 29th among Massachusetts High Schools, close to 98% of students graduated in 2016, with about 96% of those continuing to higher education.A major three-phase reconstruction and expansion of the school started in 2014 and was completed in September 2017. Most of the school was rebuilt using the original structural frame. After the complete redesign of the interior of the building, approximately 75% of classrooms now have exterior windows and direct day-lighting versus 25% in 1972. The original internal courtyard was enclosed to create the 2-story dining commons and assembly space. Winchester High School remained in use during construction.

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 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 Jacob Stanton House is a historic house in Winchester, Massachusetts, United States. It is a 2+1⁄2-story wood-frame house with a gabled front portico supported by two-story smooth columns. The main facade and the gable end are finished in flushboarding, and the second-story balcony features an ironwork railing. The house was built c. 1840 by Deacon Nathan Brooks Johnson, a local blacksmith who may have made the balcony railings. It is Winchester's only high-style temple-front Greek Revival house. After Johnson's death it was purchased by Jacob Stanton, who built the Brown & Stanton Block in downtown Winchester.The house was listed on the National Register of Historic Places in 1989.

The Abijah Thompson House is a historic house in Winchester, Massachusetts. The 1.5-story wood-frame house was built sometime between 1835 and 1850, and is a fine local example of Gothic Revival style. Its first documented owner, Abijah Thompson, was the first president of the Winchester Historical Society. The house bears resemblance to other Gothic Revival cottages in Wellesley and Newton, particularly because of the central polygonal bay, which is flanked by steeply pitched gables. It is also somewhat similar to the Moore House at 85 Walnut Street.The house was added to the National Register of Historic Places in 1989.

The William Simonds House is a historic house in Winchester, Massachusetts. The two-story wood-frame house was built in 1877 by William Simonds, and is a good local example of Second Empire styling. It has the classic mansard roof, and a symmetrical three bay front facade. On the first floor, projecting bay windows flank the entry; their bracketed roof lines are joined to that of the wide porch that shelters the front entry. The mansard roof is pierced by dormers with rounded windows.The house was listed on the National Register of Historic Places in 1989.