Cole House (Winchester, Massachusetts)

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 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 Marshall W. Jones House is a historic house in Winchester, Massachusetts. A 2.5-story wood-frame Colonial Revival structure, it was built c. 1901 for Marshall W. Jones, a local businessman and active member of the local Board of Health. The house is sited near the Middlesex Fells Reservation, which had recently been established, making the area attractive to wealthy businessmen. The house has an asymmetrical facade dominated by differently-sized cross gables, which are decorated with half-timbering and vergeboard. There is a port cochere between the gables, supported by Tuscan columns.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 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 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 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.

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 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 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 Louis N. Maxwell House is a historic house in Winchester, Massachusetts. The 2.5-story wood-frame house was built c. 1890 for Louis N. Maxwell, and is one of the finest examples of Shingle style architecture in Winchester. Although the main roof ridge is parallel to the street, the front facade presents a cross gable with roof line that sweeps down to the first floor. The entry is recessed behind a porch area underneath this gable, and there is a turret with conical roof to the gable's left.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.