Asa Locke House

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 Joseph Remick House is a historic house in Winchester, Massachusetts. The two story stucco-clad house was built in 1909 by Joseph Remick, and is sometimes called the "Baby Sanborn House" for its resemblance to the much larger Sanborn House just down the road. The house has a central five-bay section, which is flanked by wings that are one story in front and two in back. The main section is five bays wide, with French windows on both floors. The center three on the first floor are topped by triangular pediments, while those on the second floor have keystones set just below a Greek key frieze. A balustrade rings the flat roof.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 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 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 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 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 Fowle-Reed-Wyman House is a historic First Period house in Arlington, Massachusetts. The house is a two-story wood-frame saltbox structure with integral lean-to, central chimney, and clapboard siding. Built about 1706, it is the oldest structure in Arlington, and is the best-preserved of the three First Period houses left in the town. A c. 1915 addition, sympathetic in style, extends to the rear. The house was built by John Fowle, who had inherited the land from his mother, and was sold the following year to Daniel Reed. From 1775 to 1924 the house was owned by members of the Wyman family.The house was listed on the National Register of Historic Places in 1975.

The Edmund Parker Jr. House is a historic house in Winchester, Massachusetts. The 2+1⁄2-story wood-frame house was built c. 1826, and is one of a few transitional Federal-Greek Revival houses in the town. It has the typical Federal plan of five bays wide and two deep, with a center entry framed by a Greek Revival portico. The house was built by Edmund Parker Jr., whose father was one of the first settlers in the area.The house was listed on the National Register of Historic Places in 1989.

The Capt. Josiah Locke House is a historic house in Winchester, Massachusetts. The two story wood frame Federal style house was built in 1803 by Josiah Locke, a captain in the Woburn militia (the area then being part of Woburn), in an area farmed by other members of his extended family (including his brother Asa). The interior of the house has retained significant early details, including period Federal and Greek Revival details, and very early wallpaper. The home is also notable as the residence of 9-time US Women's Figure Skating Champion Maribel Vinson Owen (1911-1961) and her daughter, 1961 US Women's Figure Skating Champion Laurence Owen (1944-1961), both of whom perished in the Sabena Flight 548 crash in February 1961.The house was listed on the National Register of Historic Places in 1979.

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 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.