This is a list of properties and historic districts in Winchester, Massachusetts, that are listed on the National Register of Historic Places.
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 Edward Hall House is a historic house in Arlington, Massachusetts. The 2+1⁄2-story wood-frame house was built c. 1890 for Mrs. Edward Hall by Charles Bacon, owner of the Felt Mills in Winchester. It is one of the most elaborate treatments of Queen Anne style in the town, with asymmetrical massing typical of the style, Art Nouveau carvings in some of its gable ends, an elaborately decorated porch, and a turret with conical roof. The interior was destroyed by fire in 1893.
The Abijah Thompson House is a historic house in Winchester, Massachusetts. The 1.5-story wood-frame house was built sometime between 1835 and 1850, and is a fine local example of Gothic Revival style. Its first documented owner, Abijah Thompson, was the first president of the Winchester Historical Society. The house bears resemblance to other Gothic Revival cottages in Wellesley and Newton, particularly because of the central polygonal bay, which is flanked by steeply pitched gables. It is also somewhat similar to the Moore House at 85 Walnut Street.
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 Arthur H. Russell House is a historic house in Winchester, Massachusetts. The 2+1⁄2-story wood-frame house was built in 1899 for Arthur H. Russell, a Boston lawyer who also served as moderator of Winchester's town meetings. The house is a distinctive local example of Medieval Revival styling, with heavily shingled elements, decorative vergeboard trim, and window styles of varying size and window pane type.
The Cole House is a historic house on Highland Avenue in Winchester, Massachusetts. Built in 1886, it is one of the town's most elaborate displays of Stick style decoration. The house was added to the National Register of Historic Places in 1989.
The Dike-Orne House was a historic house in Winchester, Massachusetts. A typical rambling New England farmstead, this c. 1850 house was one of the few mid-19th century farmhouses to survive into the late 20th century. The house was added to the National Register of Historic Places in 1989. It was demolished in 1996.
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. Edmund Dwight, the wealthy businessman who was its first owner, was married to a great-granddaughter of Thomas Jefferson. 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 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 Edward Gardner House is a historic house at Zero Gardner Place in Winchester, Massachusetts. Built about 1764, it is one of the oldest buildings in Winchester, and is also important for its association with the Gardner family, who were early settlers of the area. It 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 George Wyman House is a historic house in Winchester, Massachusetts. The 2.5-story wood-frame house was built in the late 1820s, and is a rare local example of transitional Federal-Greek Revival styling. Basically Federal in its form, with side gable roof and five bay front, its center entry with full-length sidelights is more Greek Revival in character. The house was built by George Wyman near the site of one of the first houses to be built in what is now Winchester.
The Harrison Parker Sr. House is a historic house in Winchester, Massachusetts. The 2+1⁄2-story wood-frame house was built in 1843 by Harrison Parker Sr., the owner of a local lumber mill. It is also one of the finer examples of Italianate style in the town, with a low-pitch hip roof with wide eaves decorated with brackets, and small attic windows set in the architrave. The second story windows have round-arch tops, and there are decorated porches on three sides. The interior includes well-preserved period details.
The Jacob Stanton House is a historic house in Winchester, Massachusetts, United States. It is a 2+1⁄2-story wood-frame house with a gabled front portico supported by two-story smooth columns. The main facade and the gable end are finished in flushboarding, and the second-story balcony features an ironwork railing. The house was built c. 1840 by Deacon Nathan Brooks Johnson, a local blacksmith who may have made the balcony railings. It is Winchester's only high-style temple-front Greek Revival house. After Johnson's death it was purchased by Jacob Stanton, who built the Brown & Stanton Block in downtown Winchester.
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 Kenelum Baker House is a historic house in Winchester, Massachusetts. Built in 1856 by a local master builder, it is a well-preserved example of vernacular Italianate styling. It was listed on the National Register of Historic Places in 1989.
Oak Knoll is a historic estate house in Winchester, Massachusetts. This large Queen Anne/Colonial Revival house was built in the early 1890s by Lewis Parkhurst, a partner in the publishing house of Winchester resident Edwin Ginn. Parkhurst's mansion is the last surviving late 19th-century mansion house in Winchester. The house was listed on the National Register of Historic Places in 1989.
The Patience and Sarah Gardner House is a historic house in Winchester, Massachusetts. This 2+1⁄2-story wood-frame house was built c. 1830 on land that had been in the Gardner family since the mid-17th century. Patience and Sarah Gardner were sisters who purchased the property in 1825, and lived there until their deaths in 1857 and 1864. The house is an excellent local example of vernacular Federal styling.
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.
