Henry Grover House

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 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 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 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 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 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 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 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.

Wildwood Cemetery is a historic cemetery at Palmer and Wildwood Streets in Winchester, Massachusetts. The cemetery was founded in 1851 and added to the National Register of Historic Places in 1989. This cemetery was established using part of the $3000 gift from Colonel William P. Winchester that was donated on condition that the town be named after him. It was one of the first public spaces laid out after Winchester was incorporated, on land just west of the former Middlesex Canal. It is laid out in the rural cemetery fashion popular in the mid-19th century, with winding lanes a country landscaping. The designer was Amasa Farrier of neighboring Stoneham, who used as his inspiration the published works of Andrew Jackson Downing and John Claudius Loudon. Land was purchased in 1851, and was ready for use the following year. Older graves from the small cemetery at the First Congregational Church were transferred here in 1853. As a result, the oldest dated burials are in 1805. The entrance gateway was added as part of a landscape design developed by the Olmsted Brothers in 1937.Notable persons buried in the cemetery include Massachusetts Governor Samuel Walker McCall (1851–1923), Rev. Howard James Chidley (1878–1966), engineer Harold Kilbrith Barrows (1873–1954), linguist Joshua Whatmough (1897–1964), artist Joseph Foxcroft Cole (1837–1892), and artist Dana Pond (1881–1962). Other prominent burials include philanthropist and peace activist Edwin Ginn, local developer David Skilling, and Harrison Parker, owner of a local mill. It is also the burial ground for many members of locally prominent families, including members of the Symmes, Locke, Richardson, and Johnson families.

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 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.

Snug Gables is a historic house built for Thomas Dreier by Frank Chouteau Brown in Winchester, MA. It was built in 1920 and named after Dreier's wife, Blanche "Snug" Drier. Dreier ran the "Thomas Dreier Service" out of a print shop in the basement, which distributed advertising publications and motivational short stories to area business leaders. After Brown completed a project in 1923 to improve the grounds, it was featured in the August 1923 US edition of what was then known as Country Life Magazine. The house was also featured in advertisements for La Touraine coffee in newspapers throughout New England and New York. One of these was titled "Where Thomas Dreier Lives and Works," describing the household's reputation for hospitality. Another version entitled "Mrs. Thomas Dreier Keeps Here 21 Separate Accounts" notes the organization and careful approach of the matriarch, which leads her to serve La Touraine coffee.Dreier wrote "Sunshine on the Business Trail" at Snug Gables, and several of the short stories within describe the house. Short works by Dreier are engraved on bronze plaques around the property. The Dreiers sold Snug Gables in 1933. After several short term tenants, and the Armstrong and Knox families, each of which owned it for more than a decade, it was purchased in 1968 by the noted physician Alexander Leaf. It remained in the Leaf family until shortly after Alexander's death in 2013.Mr. Brown's architectural drawings and photos of the house are on file at Historic New England. Mr. Dreier's records also contain detailed information about the property, and are on file at the University of South Florida. Snug Gables is listed in the Society of Architectural Historians "Buildings of Massachusetts: Metropolitan Boston."