Winchester Highlands station

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.

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 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 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 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 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.

Cross Street station was an MBTA Commuter Rail station in northern Winchester, Massachusetts, on the border with Woburn. The station first opened in the mid-1840s as Richardson Row on the Woburn Branch Railroad, part of the Boston and Lowell Railroad (B&L). It was renamed Cross Street in 1876. The Boston and Maine Railroad (B&M) leased the B&L in 1887, built a new depot at Cross Street in 1893, and replaced it with a concrete shelter in 1955. The Massachusetts Bay Transportation Authority (MBTA) began subsidizing service on the Woburn Branch in 1965 and purchased the line in 1976. The station was closed along with the Woburn Branch in 1981.

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 House at 114 Marble Street in Stoneham, Massachusetts is a well-preserved Gothic Victorian cottage, built c. 1850. It is a 1+1⁄2-story wood-frame house with a rear ell, sheathed in wooden clapboards. It has a front gable centered over the main entry, which features turned posts and balusters, and a Stick-style valance. Windows in the gable ends have pointed arches characteristic of the style. The front gable is decorated with vergeboard.The house was listed on the National Register of Historic Places in 1984.

The Charles Russell House is a historic house at 993 Main Street in Winchester, Massachusetts. The 2+1⁄2-story wood-frame house was built by Charles Russell in 1841, on a site that was one of the first settled in what is now Winchester. The five-bay facade has a center entry that is framed by sidelight and transom windows, and is sheltered by a portico with fluted Ionic columns. The house also has corner pilasters and a high entablature.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.