Shelter Island Windmill

Sylvester Manor is a historic manor on Shelter Island in Suffolk County, New York, USA.

Manhanset Chapel, also known as Mechanics' Hall, is a historic nondenominational chapel at 24 N. Ferry Road in Shelter Island, Suffolk County, New York. It was built in 1890 and moved to its present site in 1924. It was originally located on the grounds of the Manhaset House Hotel. It is a modest, frame Gothic Revival style structure. It consists of a gabled nave; a prominent, square engaged tower; a distinct chancel with a lower gabled roof; and a rear entrance wing.It was added to the National Register of Historic Places in 1997.In 1986, the Osofsky family donated the chapel to the Shelter Island Historical Society, which restored it to the 1924 period of its significance when it was used by the Junior Order of United American Mechanics. In 2011, Randy Osofsky repurchased the chapel with her husband, Stephen Kessler, for use as an arts and events space for Shelter Island.

James Havens Homestead is a historic home located at Shelter Island in Suffolk County, New York. The house was built in 1743 and expanded in the early- mid-19th century. It is a large wood-frame building with wood-shingle sheathing, broad gable roof, wraparound porch, and rear wings. The main section includes a two-story, three-bay side-entrance-hall dwelling which was enlarged to four bays with a wide two-story, one-bay addition. Also on the property is a small wood-frame shed.It was added to the National Register of Historic Places in 1986.The house is owned by the Shelter Island Historical Society and operated as a historic house museum.

Shelter Island Heights is a hamlet and census-designated place (CDP) located in the Town of Shelter Island, in Suffolk County, New York, United States. It is located on the north side of Shelter Island, surrounding the village of Dering Harbor. The population was 1,601 at the time of the 2020 census.

Shelter Island is an island town in Suffolk County, New York, United States, near the eastern end of Long Island. The population was 3,253 at the 2020 United States census.

Shelter Island is a hamlet and census-designated place (CDP) within the Town of Shelter Island in Suffolk County, New York, United States. The population was 1,602 at the time of the 2020 census. The community is on Shelter Island, between the North and South Forks of Long Island, and is reachable only by ferry. Many of the properties are owned by wealthy New York City residents who use the island as a weekend retreat. Shelter Island is characterized by a quieter and less social lifestyle than that of the nearby Hamptons.

Dering Harbor is a village in the Town of Shelter Island, in Suffolk County, New York, United States. As of the 2020 census, the village population was 50, making it the least populous village in the State of New York. The Incorporated Village of Dering Harbor is located on the northern side of Shelter Island, east of the hamlet of Shelter Island Heights.

Shelter Island Heights Historic District is a national historic district located at Shelter Island Heights in Suffolk County, New York. There are 141 contributing buildings and one contributing structure.It was added to the National Register of Historic Places in 1993.

Shelter Island Country Club is a historic country club located at Shelter Island in Suffolk County, New York. The club was established in 1901 and consists of a nine-hole golf course, club house, driving range, and maintenance facility. The club house is a two-story Colonial Revival-style wood-frame building with a side-gabled gambrel roof with five dormer windows on both the east and west elevations. It features a full-length front porch on the east and north sides.It was added to the National Register of Historic Places in 2009.

Union Chapel is a historic Methodist chapel located in Shelter Island Heights, Suffolk County, New York. It was built in 1875 and is a wood-frame structure with wood-shingle sheathing. The chapel's main three-bay facade has a 2+1⁄2-story bell tower with a double-door center entrance at its base; a small porch shelters the entry. It is the most important extant structure associated with the Shelter Island Heights Grove and Camp Meeting Association, a Methodist camp established in 1872.It was added to the National Register of Historic Places in 1984.

The Smith-Ransome Japanese Bridge of South Ferry Hills on Shelter Island, New York is one of the first 'reinforced concrete construction' structures built in North America by engineer Ernest L. Ransome for the mineral prospector known as the "Borax King", Francis Marion Smith. Installed in the late 19th century at Smith's East Coast estate, 'Presdeleau', it is an example of ferro-concrete construction enabling an elegant design of what was a popular early 20th century period piece, the Japanese style bridge. It is listed on the New York State and National Register of Historic Places as a significant historical landmark and one of the last surviving two by Ernest Ransome.

Greenport is the terminus of the Main Line (Greenport Branch) of the Long Island Rail Road. It is officially located at Wiggins Street and Fourth Street in the Village of Greenport, New York, although the property spans as far east as 3rd Street and the Shelter Island North Ferry terminal.