Shepherd Brooks Estate

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 Horace Hatch House is a historic house in Winchester, Massachusetts. Originally located on Lloyd Street, this c. 1835 Greek Revival cottage was moved to its present location on Grove Street c. 1843. It is a locally rare example of a side gable Greek Revival cottage whose roof overhangs its full-width front porch. The house is similar to the nearby Hovey-Winn House, and may have been built by the same housewright, John Coats.The house was listed on the National Register of Historic Places in 1989.

The Deacon John Symmes House is a historic house in Winchester, Massachusetts. Built about 1807, it is a fine local example of Federal period architecture, and is also significant for its association with the Symmes family, who were among Winchester's earliest settlers. The house was listed on the National Register of Historic Places in 1989.

The Thomas Ayer House is a historic house at 8 Grove Street in Winchester, Massachusetts. Built about 1864, it is a conservative but detailed example of early Italianate architecture. It was built for a prominent local businessman and politician. The house was listed on the National Register of Historic Places in 1989.

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 Mystic Lakes, consisting of Upper Mystic Lake and Lower Mystic Lake, are closely linked bodies of water in the northwestern suburbs of Boston, Massachusetts. The lakes lie at an elevation of 1 meter above sea level, within the towns of Winchester, Arlington, and Medford, Massachusetts. Upper Mystic Lake is fed by the Aberjona River, and drains south, over the Mystic Dam, into Lower Mystic Lake, which in turn empties into the Mystic River and then Boston Harbor.

The Marshall Symmes House is a historic house in Winchester, Massachusetts. Built c. 1817, it is a rare local example of Federal period brick-end house, and is further notable for its association with the Symmes family, who were among Winchester's earliest settlers. The house was listed on the National Register of Historic Places in 1989.

The Mystic Dam (and its gatehouse) are a historic dam and gatehouse between Lower and Upper Mystic Lakes in the suburbs north of Boston, Massachusetts. The dam was built in 1864–65 by the Charlestown Water Commission (Charlestown then being separate from Boston) as part of a water supply system. It was located at a narrow point between the Lower and Upper Mystic Lakes, with its west end in Arlington and its east end in Medford. The water system it was a part of eventually merged into the Metropolitan District Commission (MDC), predecessor to the Massachusetts Water Resources Authority (MWRA) and the Massachusetts Department of Conservation and Recreation (DCR).As built, the dam was over 1,500 feet (460 m) long and 16 feet (4.9 m) high, with most of that length (about 1,000 feet (300 m)) consisting of earthen embankments lined with riprap and puddle clay. Near its center is a spillway area consisting of a series of square columns constructed of granite blocks and a masonry apron. These columns are grooved on their inner faces to facilitate the installation of stop logs. A wooden walkway with a plank railing ran across the top of the dam. A wooden fish ladder was built, but removed at a later date. A gatehouse on the Medford side was used to connect the upper lake to a brick-lined aqueduct that delivered the water to Charlestown. The lake area impounded by the dam is 186 acres (75 ha).The dam and gatehouse were each listed on the National Register of Historic Places in 1990. By the early 2000s, the dam was known to not be in very good condition, with failing spillway masonry, erosion, and other damage to the dam's stonework. A major storm in 2006 flooded portions of the surrounding area, and highlighted the potential inability of the dam to handle a significant high-water event, leading to catastrophic flooding of downstream areas. Between 2010 and 2012 major work was undertaken to improve the dam's condition. A new spillway was constructed to the east of the old spillway, which received a new spillway apron. Work was done on the embankments and the shores near the upper areas of the dam, and a new fish ladder and bridge were built. The historic gatehouse was also rehabilitated, and modern controls were added, enabling improved control over the water levels behind the dam.

Mystic Valley Parkway is a parkway in Arlington, Medford, Somerville, and Winchester, Massachusetts. It is listed on the National Register of Historic Places, and forms part of Route 16.

The Marshall Symmes Tenant House is a historic house in Winchester, Massachusetts, USA. Built in the 1870s as a rental property on land owned by Marshall Symmes (1789-1889), this Italianate house is notable for its association with the Symmes family, who were among Winchester's first settlers. 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.

Wedgemere station is an MBTA Commuter Rail station in the southeast portion of Winchester, Massachusetts. Wedgemere is served by all Lowell Line trains, as well as a small number of Haverhill Line trains which run via the Wildcat Branch. The station consists of two platforms serving the line's two tracks on an elevated grade. The 1957-built station building, largely unused, is adjacent to the inbound platform. After several years of work, the station was made fully accessible in February 2013.