Edward Braddock House

Winchester Hospital located in Winchester, Massachusetts is a notable hospital in northwest suburb of the city of Boston, United States. It is affiliated with Lahey Health. The hospital provides inpatient service and integrated home care to the population residing in Winchester, Woburn, Reading, Wilmington, North Reading, Stoneham, Burlington, Billerica, Medford, Malden, Wakefield, Tewksbury and several other surrounding communities.

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.

The Zachariah Richardson House is a historic house in Winchester, Massachusetts. The 2.5-story wood-frame house has an irregular six-bay facade, a side gable roof, and clapboard siding. It was built in 1818, but may incorporate elements of a schoolhouse built in 1794, which previously stood on that site. The house is significant for its association with the Richardson family, the first colonial settlers of the area (arriving in the Washington Street area by 1642).The house was listed on the National Register of Historic Places in 1989.

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 Highlands station was an MBTA Commuter Rail Lowell Line station located at Cross Street in the northern part of Winchester, Massachusetts. It originally opened in the mid-19th century under the Boston and Lowell Railroad (B&L) as a flag stop called North Winchester. In 1877, a local real estate developer constructed a new station building, which was renamed Winchester Highlands. The B&L became part of the Boston and Maine Railroad (B&M) in 1887. Service to the station gradually decreased in the 20th century, and the depot was replaced by a wooden shelter around 1943. The Massachusetts Bay Transportation Authority (MBTA) began subsidizing service on the line in 1965. Winchester Highlands and two other stations with low ridership were closed by the MBTA in June 1978.

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.

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 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 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.