Winchester is a town in Middlesex County, Massachusetts, United States, 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 Albert Ayer House is a historic house in Winchester, Massachusetts. Built around the year 1865, it is a conservative but detailed example of early Italianate architecture. It was built for a locally prominent civic leader. 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 Alfred Vinton House is a historic house at 417 Main Street in Winchester, Massachusetts. It is a two-story wood-frame structure, three bays wide, with a side gable roof that has bracketed eaves. The front is symmetrically arranged, with a center entrance flanked by sidelight windows, and set under an elaborately decorated front porch. A round-arch window stands above the entrance. Gardner Symmes, a local builder, built the Italianate house c. 1854, and may have lived in it before Alfred Vinton, a local lawyer who married into the Symmes family, bought it in 1862. It remained in the Vinton family into the 1920s.
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 Asa Locke House is a historic house in Winchester, Massachusetts. Built in the mid-19th century, it is a well-preserved local example of a side-hall Italianate farmhouse. It is also notable for its association with the locally prominent Locke family, who settled the area in 1699. The house was listed on the National Register of Historic Places in 1989.
The Edmund Dwight House is a historic house at 5 Cambridge Street in Winchester, Massachusetts, straddling the town line with Arlington. It was built in 1858 in an Italianate style. It was one of the first and grandest country houses built in Winchester at a time when Boston businessmen were seeking to build such houses. The house's design is believed to be based loosely on that of Jefferson's Monticello. The house is sited for an expansive view of the Upper Mystic Lake. This residence was also home to Claude Shannon, the father of Information theory, and his wife Betty Shannon. While living there, they installed a chair lift that took the rider from the home down to the lake.
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 Everett Avenue–Sheffield Road Historic District is a historic district encompassing one of the finest residential districts from the turn of the 20th century in Winchester, Massachusetts. The district is roughly triangular in shape, bounded in the north by Bacon Street, on the west by Church Street, Sheffield West, and Sheffield Road, and on the south and heast by the Upper Mystic Lake and Mystic Valley Parkway. It is characterized by winding roads, with relatively large houses on well-proportioned lots. Most of the houses were built between 1890 and 1916, and all exhibit some architectural sophistication. A significant number of properties were designed by either F. Patterson Smith or Dexter Blaikie, two local architects. The district was listed on the National Register of Historic Places in 1989.
The Firth–Glengarry Historic District encompasses a residential area of Winchester, Massachusetts consisting of well-preserved high quality houses built mainly between 1880 and 1900. The district lies between Wildwood Street and Wedge Pond, and includes properties on Pine Street, Glengarry Road, Grassmere Avenue, Dix Street, and Wildwood Street; houses on Curtis Street and Curtis Circle, are excluded from the district. Much of the area was laid out by developer William Firth, and many of its houses were designed by Boston architect Robert Coit. The 13.44-acre (5.44 ha) district was listed on the National Register of Historic Places in 1989.
The Hovey-Winn House is a historic house at 384 Main Street in Winchester, Massachusetts. The 1+1⁄2-story Greek Revival cottage was built c. 1841 by John Coats, a local housewright who built a number of houses along Main Street. It is one of a small number of local houses (the nearby Horace Hatch House is another) with a side gable roof that overhangs a full-width Doric porch. The house in the 19th century had a number of locally prominent individuals, include Reverend William Eustis, druggist Josiah Hovey, and Hovey's son-in-law Denis Winn, who owned the town's first livery stable.
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 Robert Bacon House is a historic house at 6 Mystic Valley Parkway in Winchester, Massachusetts. Built about 1830, it is one of the town's only surviving examples of high-style transitional Federal/Greek Revival styling. It was built for a local businessman whose nearby mills (no longer surviving) were major employers of the period. The house was listed on the National Register of Historic Places in 1989.
The historic house at 38 Rangeley Road in Winchester, Massachusetts is one of three Panel Brick in an exclusive late 19th century subdivision. The house was listed on the National Register of Historic Places in 1989 as the Samuel Elder House, on the incorrect belief that it was the home of Samuel Elder, a prominent Boston lawyer.
St. Mary's Catholic Church is a parish church of the Catholic Church in Winchester, Massachusetts, within the Archdiocese of Boston. It is noted for its historic church at 159 Washington Street, which was listed on the National Register of Historic Places in 1989, reflecting its important role among the local Irish Catholic community. The parish also operates St. Mary's Early Learning Center, a preschool and kindergarten, the successor to St. Mary’s School, a parochial school which operated until 2020.
The Thomas Ayer House is a historic house at 8 Grove Street in Winchester, Massachusetts. Built about 1864, it is a conservative but detailed example of early Italianate architecture. It was built for a prominent local businessman and politician. The house was listed on the National Register of Historic Places in 1989.
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.
Wedgemere station is an MBTA Commuter Rail station in the southeast portion of Winchester, Massachusetts, served by the Lowell Line. The station has two side platforms serving the line's two elevated tracks. The 1957-built station building, largely unused, is adjacent to the inbound platform. After several years of work, the station was made fully accessible in February 2013.
The Wedgemere Historic District encompasses the largest single 19th-century residential development of Winchester, Massachusetts. It is one of the town's largest surviving 19th-century residential subdivisions, with a concentration of high-quality residences built between about 1890 and 1920. The district was listed on the National Register of Historic Places in 1989.
Wildwood Cemetery is a historic cemetery at Palmer and Wildwood Streets in Winchester, Massachusetts.
Winchester Center station is a MBTA Commuter Rail station in Winchester, Massachusetts, served by the Lowell Line. The station is located on a viaduct in downtown Winchester, with two accessible side platforms serving the line's two tracks. The station was temporarily closed on January 8, 2021 due to structural deterioration. The first portion of the rebuilt station opened on October 1, 2024, with the remaining portion opened in June 2025.
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 Hospital located in Winchester, Massachusetts is a notable hospital in northwest suburb of the city of Boston, United States. It is affiliated with Beth Israel 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.
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.
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 2023, with about 96% of those continuing to higher education.