Wildwood Cemetery

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."

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.

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 Carr-Jeeves House is a historic house in Winchester, Massachusetts. Built in 1869, it is fine local example of Second Empire architecture. It 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 DeRochmont House is a historic house in Winchester, Massachusetts. Built about 1876 by a Maine lumber magnate as part of the exclusive Rangeley Estate, it is one three examples of Panel Brick Queen Anne architecture in the town. 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 house was listed on the National Register of Historic Places in 1989.

The Skillings Estate House is a historic house in Winchester, Massachusetts. Built about 1880 by a Maine lumber magnate David Skillings, it is one of four houses he built as part of his exclusive Rangeley Estate. The house was listed on the National Register of Historic Places in 1989.

The historic house at 38 Rangeley Road in Winchester, Massachusetts is one of three Panel Brick in an exclusive late 19th century subdivision. The house was listed on the National Register of Historic Places in 1989 as the Samuel Elder House, on the incorrect belief that it was the home of Samuel Elder, a prominent Boston lawyer.

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 house was added to the National Register of Historic Places in 1989.

Winchester Center station is a temporarily closed MBTA Commuter Rail station in Winchester, Massachusetts. The station, located on a viaduct in downtown Winchester, was closed effective January 8, 2021 due to structural deterioration. Prior to closure, it served all Lowell Line trains as well as a limited number of Haverhill Line trains which run via the Wildcat Branch. Winchester Center station was not accessible prior to the closure, but accessible high-level platforms are being added during renovations taking place from December 2021 to April 2024.

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.