Jacob Stanton House

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 house was listed on 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.

The Parker House is a historic house in Winchester, Massachusetts. This two story wood-frame house was probably built in the 1850s by Kenelum Baker, a local builder, and is an elaborately styled Italianate house. It has wide eaves studded with paired brackets, and the porch, eave, and cupola all have a simple scalloped molding. The square cupola has round-arch windows, and the porch wraps around three sides of the house.The house was listed on the National Register of Historic Places in 1989.

The Hutchinson-Blood House is a historic house at 394-396 Main Street in Winchester, Massachusetts, United States. The 2.5-story wood-frame house was built around 1840 by John Coats, a local housewright. The Greek Revival house was built by Coats for his in-laws, Samuel and Lucetta Hutchinson. It is basically Federal in styling, although it has a Greek Revival entry surround. The main house has had a two-story addition added to the rear, as well as a side porch.The house was listed on the National Register of Historic Places in 1989.

The Sharon House is a historic house in Winchester, Massachusetts. The 2.5-story wood-frame house was built c. 1835, and has basic Greek Revival styling. It is most notable as including a rare surviving remnant of the shoe manufacturing industry, which was a cottage industry in the area in the first half of the 19th century. The building's rear ell, a two-story structure, is believed to have originally been used for that purpose. It is not known if it (the ell) was built in place or moved to that location and attached to the house. The house also stands adjacent to the site of the Black Horse Tavern, and early 18th century landmark.The house was listed on the National Register of Historic Places in 1989.

The John Mason House is a historic house in Winchester, Massachusetts. This two-story wood-frame house was built sometime in the 1860s, probably for Joshua Stone, who sold it to John Mason sometime before 1875. Mason was one of the first Boston businessmen to establish a suburban residence in Winchester. The house has a variety of high-style Italianate features, including a characteristic low-pitch hip roof with decorative brackets, and a three-bay front facade in which paired narrow windows are topped by decorative framing. The front entry is sheltered by a portico supported by multiple columns and pilasters, with a bracketed roof.The house 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 house was listed on the National Register of Historic Places in 1989.

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 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 Trowbridge-Badger House is a historic house in Winchester, Massachusetts. The large 2.5-story house was built c. 1886, and is an excellent local representative of predominantly Queen Anne styling with Colonial Revival features. The house's irregular roof line, with many gables and projecting sections, is typically Queen Anne, while the shingled porch with Tuscan columns is Colonial Revival. Little is known of its early owners beyond their names.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.The building was listed on the National Register of Historic Places in 1987, 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.