James H. Mann House

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.

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 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.

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.

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.

The Moore House is a historic house in Winchester, Massachusetts. The 1+1⁄2-story Gothic Revival house was probably built sometime in the 1840s, possibly by George Moore, a local builder whose family was listed as resident there 1865–1931. The house is distinctive for having three steeply pitched gable dormers in front, decorated with vergeboard, and for a small mansard-roofed tower added to the rear in the 1870s. The single-story front porch has a flat roof, with a decorative jigsawn valance.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 Edward A. Brackett House is a historic octagon house at 290 Highland Avenue in Winchester, Massachusetts. Built in the early 1850s by sculptor Edward Augustus Brackett, and based on popular plans described by Orson Squire Fowler, it is Winchester's only octagonal house. The house was listed on the National Register of Historic Places in 1989.

The Edward Braddock House is a historic house in Winchester, Massachusetts. Built in 1893, it is a high-quality example of Colonial Revival architecture with Shingle style elements. The house was listed on the National Register of Historic Places in 1989.

The Cole House is a historic house on Highland Avenue in Winchester, Massachusetts. Built in 1886, it is one of the town's most elaborate displays of Stick style decoration. The house was added to the National Register of Historic Places in 1989.