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Beechwood is a Hudson River estate in Scarborough-on-Hudson, in Briarcliff Manor, New York. The estate was most notably the home of Frank A. Vanderlip and his family, and is a contributing property to the Scarborough Historic District. The house and property were owned by the Vanderlip family from 1906 to 1979.

The Downtown Ossining Historic District is located at the central crossroads of Ossining, New York, United States, and the village's traditional business district known as the Crescent. Among its many late 19th- and early 20th-century commercial buildings are many of the village's major landmarks—three bank buildings, four churches, its village hall, former post office and high school.

Archville is a hamlet in Mount Pleasant, New York. The hamlet consists of residences, businesses, and a fire station on Union Street, Arch Hill, and Requa Street, all abutting U.S. Route 9. Directly across Route 9 lies Rockwood Hall, part of the Rockefeller State Park Preserve. The volunteer Archville Fire Department serves the hamlet and surrounding area, from the Hudson River to Pocantico Lake and from the edge of Briarcliff Manor to the edge of Sleepy Hollow.

Ossining is a town located along the Hudson River in Westchester County, New York, United States. The population was 37,674 in the 2010 census. It contains two villages, the Village of Ossining and part of Briarcliff Manor, the rest of which is located in the Town of Mount Pleasant. Ossining is the location of Sing Sing maximum-security prison.

Highland Cottage, also known as Squire House, is located on South Highland Avenue (U.S. Route 9) in Ossining, New York, United States. It was the first concrete house in Westchester County, built in the 1870s in the Gothic Revival architectural style. In 1982 it was listed on the National Register of Historic Places; almost 30 years later, it was added to the nearby Downtown Ossining Historic District as a contributing property.

The Scarborough Day School was a private school in Scarborough-on-Hudson, in Briarcliff Manor, New York. Frank and Narcissa Cox Vanderlip established the school in 1913 at their estate, Beechwood. The school, a nonsectarian nonprofit college preparatory day school, taught students at pre-kindergarten to twelfth grade levels and had small class sizes, with total enrollment rarely exceeding 150 students.

Ossining High School (OHS) is a comprehensive public high school located in Ossining, New York, United States, along the Hudson River in northern Westchester County, New York. Serving grades 9 through 12, it is the sole high school within the Ossining Union Free School District. The school serves the entirety of the village of Ossining, portions of the Village of Briarcliff Manor, Town of Ossining, and Town of New Castle, as well as a very small southern portion of the Town of Yorktown.

Sleepy Hollow Cemetery in Sleepy Hollow, New York, is the final resting place of numerous famous figures, including Washington Irving, whose story "The Legend of Sleepy Hollow" is set in the adjacent burying ground at the Old Dutch Church of Sleepy Hollow. Incorporated in 1849 as Tarrytown Cemetery, the site posthumously honored Irving's request that it change its name to Sleepy Hollow Cemetery.

Sleepy Hollow is a village in the town of Mount Pleasant, in Westchester County, New York. The village is located on the east bank of the Hudson River, about 30 miles (48 km) north of New York City, and is served by the Philipse Manor stop on the Metro-North Hudson Line. To the south of Sleepy Hollow is the village of Tarrytown, and to the north and east are unincorporated parts of Mount Pleasant.

Peabody Preserve is a 40-acre (0.16 km2) natural land area located in between the Hudson River and Fremont Pond, in Sleepy Hollow, New York, United States. The Preserve contains hiking trails, multiple habitats, wetlands, a retaining pool and diverse species of flora and fauna. The Reserve was created to protect and restore native ecological communities and wetlands, serve as an outdoor classroom for students and teachers, and provide recreational opportunities to all visitors.