Fort Heath

Grovers Cliff is a shoreline escarpment at Broad Sound near the Port of Boston and by extension, the landform extending into the sea (headland) that is the "Highlands" section of Winthrop, Massachusetts. The headland is at the north end of Winthrop Beach and is noted for an 1847 survey station, WWI & II fortifications and a Cold War nuclear bunker used by the US Army, USCG, USN, USAF, and FAA as Fort Heath, the eponym of the landform's current apartment complex. A northern area of the headland is the municipal Small Park and the remainder is primarily the Fort Heath Apartments. Streets include Highland Avenue and Pond Street which had been constructed by the 1930s at the perimeter of Fort Heath.

The Highland School, also the Arthur W. Dalrymple School, is a historic school building at 36 Grovers Avenue in Winthrop, Massachusetts. The Georgian Revival two story brick building was built in 1920–21 to replace a nearby school that burned down in 1920. It was built on the site of the Leighton Resort, a popular summer destination. The school's later dedicatee was a local resident who taught at the school and later became Winthrop's superintendent of schools.The building was added to the National Register of Historic Places in 2014.

The Deane Winthrop House is an historic house at 34 Shirley Street in Winthrop, Massachusetts. Deane Winthrop (1623–1704) was the sixth son of the second colonial governor of the Massachusetts Bay Colony, John Winthrop. The oldest part of the house was built about 1675 with an addition made in 1696. It is currently owned by the Winthrop Improvement and Historical Association and is open to visitors by appointment. This building is one of the oldest wood frame houses in the country and is the oldest continuously lived in home in the United States. The house was added to the National Register of Historic Places in 1990. In 2009, an addition was made to the barn to store Winthrop Improvement and Historical Association artifacts and documents. Originally thought to have been constructed earlier, a dendrochronology survey of the tree rings in 2002 confirmed that the earliest part of the house was built in 1675.

Winthrop Parkway is a historic parkway in Revere, Massachusetts. The parkway, built between 1909 and 1919 and now designated as part of Route 145, runs for about 0.75 miles (1.21 km), from Eliot Circle (the junction with the Revere Beach Parkway and Revere Beach Boulevard) southeast to the Revere-Winthrop line. Acquisitions for its construction represent the last public purchase of oceanfront lands in Revere. It was listed on the National Register of Historic Places in 2004.

Fort Banks was a U.S. Coast Artillery fort located in Winthrop, Massachusetts. It served to defend Boston Harbor from enemy attack from the sea and was built in the 1809 during what is known as the Endicott period, a time in which the coast defenses of the United States were seriously expanded and upgraded with new technology. Today, the fort's mortar battery is on the National Register of Historic Places. The fort was active during World War II as the site of the Harbor Defense Command Post (HDCP) for the Harbor Defenses of Boston, and was greatly expanded with numerous temporary structures (see 1938 map at top left). Because of its campus-like appearance and the fact that it was located on land, close of Boston, the fort was known as "The Country Club" by Coast Artillery soldiers pleased to be posted there. Fort Banks was named for Nathaniel P. Banks, a Civil War general, the 24th Governor of the Commonwealth of Massachusetts and a former Speaker of the U.S. House of Representatives.

The Harbor Defenses of Boston was a United States Army Coast Artillery Corps harbor defense command. It coordinated the coast defenses of Boston, Massachusetts from 1895 to 1950, beginning with the Endicott program. These included both coast artillery forts and underwater minefields. The command originated circa 1895 as the Boston Artillery District, was renamed Coast Defenses of Boston in 1913, and again renamed Harbor Defenses of Boston in 1925.

Winthrop High School is a public four-year high school in Winthrop, Massachusetts, United States. It is a part of Winthrop Public Schools. The current school building, with 187,917 square feet (17,458.1 m2) of space, had a cost of $80.2 million, with about $42.5 million or 60% of the costs covered by the Massachusetts School Building Authority. The building is shared with Winthrop Middle School. The first steel beams were put up in 2015 and opening was to occur in fall 2016. Note: Winthrop Middle School and Winthrop High School are housed in the same building, but are two separate and distinct schools with their own administration.

Winthrop Beach is the main beach of Winthrop, Massachusetts. It is located along Winthrop Shore Drive, spanning the roadway. The beach begins off Crest Avenue at an area known as the "Green Bars", named for the green railings along the seawall. The beach ends at the base of Water Tower Hill. The ocean has five wave breakers known as the "Five Sisters" offshore to protect nearby neighborhoods from the large swells that occur during storms. Winthrop Beach is open year round to the public from dawn to dusk, and lifeguards are on duty from late June to early September.

Lewis Lake is a lake in the U.S. state of Massachusetts. It is located 0.5 mi southeast of Winthrop.

The Mary T. Ronan School, originally the Bradstreet Avenue School, is a historic former school building at 154 Bradstreet Avenue in Revere, Massachusetts. The 2+1⁄2-story Classical Revival style brick building was built in 1896, during a period of rapid growth in the city's Beachmont neighborhood. It was eventually renamed in honor of one of its early principals. The building was converted to senior housing in 1981. It is architecturally noted for its elaborate entrance section, with full-height brick pilasters at the corners, and a round-arch opening flanked by narrow round-arch windows.The building was added to the National Register of Historic Places in 1982.

Winthrop Shore Drive is a historic parkway in Winthrop, Massachusetts. The mile-long parkway runs through the Winthrop Beach Reservation, and is administered by the Massachusetts Department of Conservation and Recreation (DCR). The parkway is one of a series of ocean parkways (and the second one built) that make up a network of parkways connecting major open spaces in the Greater Boston area. Both the parkway and reservation were designed in the mid-1890s by Charles Eliot for the Metropolitan Parks Commission, a predecessor to the DCR. Land was acquired for the parkway in 1899, and construction was largely completed in 1900.The parkway was listed on the National Register of Historic Places in 2004.

The Winthrop Center/Metcalf Square Historic District encompasses the historic center of the city of Winthrop, Massachusetts. Although the area was settled early in Massachusetts history (c. 1637), the Winthrop peninsula remained sparsely populated until the 19th century. Its central area did not begin significant development until there was some industrial development in the first half of the 19th century, and accelerated with the arrival of the railroad later in the 19th century. It is centered on Metcalf Square, at the junction of Pauline, Hermon, and Winthrop Streets; the district extends northward along Hermon and Winthrop, and also includes properties as far east as Cross Street.Most of the over 100 buildings in the district are residential, and were built between about 1880 and 1940. The oldest house in the district is believed to be 257 Winthrop Street, which is thought to have been built in the 1790s and restyled with Greek Revival details in the 19th century. (This is in contrast to Winthrop's oldest house, the c. 1675 Deane Winthrop House, which lies outside the district.) The most prominent buildings are the cluster of municipal and religious buildings around Metcalf Square: the Town Hall (1929) and Library (1898) are both Renaissance Revival structures, while the police station (formerly a post office) is a Colonial Revival building from 1932, and the Methodist Church is a Colonial/Classical Revival from 1930.There are some fine examples of well-preserved 19th-century architectural styles in the district. Noteworthy Italianate houses include 11 George Street, whose gables are studded with decorative brackets indicative of the style, and 233 Winthrop Street, the city's only towered Italianate villa. Particularly good examples of Queen Styling are found at 180 and 272 Winthrop; the latter in particular is distinguished for its turret, which has a bulbous roof and carved wooden panel decorations.The district was listed on the National Register of Historic Places in 2010.