Joseph Remick House

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 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 house was listed on the National Register of Historic Places in 1989.

The Sanborn House is one of the few surviving country house models in Winchester, Massachusetts. Nine and one-half acres of property was purchased in 1904 by Oren Sanborn, younger son of James Sanborn, the co-founder of Chase & Sanborn Coffee Company.

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.This residential area was not formally laid out as a subdivision. It was in this area that Massachusetts politician and orator Edward Everett had an estate in the 1850s; it is for him that Everett Avenue is named. The earliest house is at 8 Everett Avenue, built in 1880, in the Colonial Revival style, which predominated in construction until the advent of the 20th century. One of the finest examples of this style is the Smith-designed Chadwick House at 24 Everett Avenue, combining stucco walls with brick trim on the corners and window trim.Houses built in the 20th century tended by be either Neo-Rationalist, Tudor Revival, or Craftsman in their styling. Many houses in this time were designed either by Dexter Blaikie, Phineas Nickerson, or both in partnership. A house Blaikie designed for himself, at 45 Everett Avenue, is a relatively simple example of Tudor Revival styling. A more elaborate example of that style, designed by Blaikie and Nickerson is the Martin House at 23 Sheffield Road. The district includes a total of 129 properties, of which only 20 do not contribute to its significance. These are mostly excluded because they do not meet the normal 50-year cutoff period for historical significance, although a few buildings have been compromised by unsympathetic alterations.

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. 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 house is a 2+1⁄2-story wood-frame structure, originally finished in clapboard siding. It is basically rectangular, with a rounded central bay on the eastern facade, facing the lake. A single-story porch wraps around three sides of the building. Significant alterations were made to the house in the 1890s, including the stuccoing of the exterior, and the addition of a two-story ell to the northeast corner. These changes were made under the auspices of local architect Robert Coit. A second, single-story, addition was made to the northwest corner in 1985. The original 12-acre (4.9 ha) property purchased by the Dwights was subdivided c. 1940, leaving the house on just 2 acres (0.81 ha). The house's stable was then converted to a residence, and stands on an adjacent lot in Arlington.The house was added to the National Register of Historic Places in 1989.

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.

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.

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 (c. 1660).The house was listed on the National Register of Historic Places in 1989.

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 Henry Grover House is a historic house at 223–225 Cambridge Street in Winchester, Massachusetts. The wood-frame 2+1⁄2-story double house was built in the 1880s by Henry Grover, who farmed 25 acres (10 ha) of surrounding land. In the late 20th century, the Purcell family operated a flower stand on the property known as "Purcell's Pansy Patch". When the site was developed for housing beginning in 2009, the house was rehabilitated as part of the development.The house was built in 1885 and added to 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.Prior to William Firth's consolidation of land ownership southwest of Wedge Pond in the late 19th century, this area of Winchester was sparsely inhabited. The oldest house in the area is an 1843 Greek Revival structure at 3 Wildwood Street. Two houses were built near Wedge Pond in the 1850s and 1860s, of which the Charles Curtis House (1965, 9-11 Grassmere Avenue) is a particularly fine example of Carpenter Gothic; the Bellows House, built in 1854, is also Gothic Revival in character. In the 1880s and early 1890s three Queen Anne/Stick style houses were built, of which the Langley House (1887) at 10 Pine Street is the most elaborate.After Firth had acquired most of the land in the area, he subdivided into ample house lots, and laid out Glengarry Road and Grassmere Avenue. He hired Robert Coit to design houses which are predominantly Colonial Revival and Medieval Revival (Tudor) in character. Coit's designs used shingling to a significant degree, and mixed in features from other popular revival styles. Firth's own house at 37 Dix Street, built in 1937, is, however, a relatively straightforward Colonial Revival design, with a gambrel roof and modillioned cornice, and with gable dormers and a full-width front porch supported by Doric columns.