Isle of Wight County, Virginia

Boykin's Tavern is a historic inn and tavern located at Isle of Wight, Isle of Wight County, Virginia. The original structure was built about 1790, and expanded to two stories with a 1+1⁄2-story gambrel-roofed wing in the early 19th century. A two-story wing and two-story porch were added in 1900–1902. It has four brick external end chimneys and a standing seam metal gable roof. The interior reflects the transition between the Colonial and Federal styles. It is the only surviving structure associated with the Isle of Wight Courthouse of 1800. The building is occupied by a local history museum. It was listed on the National Register of Historic Places in 1974.

Isle of Wight is an unincorporated community in and the county seat of Isle of Wight County, Virginia, United States. Originally, Isle of Wight County was named Warrosquyoake Shire. This was changed to the current name of Isle of Wight in 1637.

Isle of Wight Academy (IWA) is a private non-profit day school located in Isle of Wight County, Virginia. It was founded in 1967 as a segregation academy. The school has students from Pre-kindergarten to 12th grade and is non-sectarian and coeducational.

Four Square is a historic home and farm located near Smithfield, Isle of Wight County, Virginia. The original structure was built in 1807, and is a two-story, five-bay, L-shaped frame dwelling. Also on the property are eight contributing domestic outbuildings, and a variety of barns and other farm buildings.It was listed on the National Register of Historic Places in 1979.

Robert Tynes House, also known as Tynes Plantation, is a historic plantation house located near Smithfield, Isle of Wight County, Virginia. The house was built in 1750 and is a two-story, three-bay, Georgian style brick dwelling with a gambrel roof. The interior features a center-passage single-pile plan. Also on the property are the contributing garden and well, smokehouse / frame shed, and kitchen foundation. In 1802, its owner Timothy Tynes granted manumission of his 81 slaves and the division of his 4,000 acre estate primarily to his slaves.It was listed on the National Register of Historic Places in 2007.

Joseph Jordan House, also known as Boykin's Quarter, Jordan's, and Hatty Barlow Moody Farm, is a historic home located near Raynor in Isle of Wight County, Virginia, United States. The original structure was built about 1795, and is a 1+1⁄2-story, three-bay, frame structure with brick ends. It was later expanded with a two-story, one room, frame addition and a one-bay kitchen ell. The house features clerestory monitors that were probably added about 1820–1840. Also on the property are a variety of contributing outbuildings.It was listed on the National Register of Historic Places in 1979.

Wolftrap Farm was a historic home located near Smithfield, Isle of Wight County, Virginia. The house was built about 1820, and is a 2+1⁄2-story, three-bay, Federal style frame dwelling. It was a one-story rear elevation surmounted by a double tier of dormer windows. The house has a double-pile, hall-parlor plan and measures approximately 32 feet, 6 inches, square. The house has been dismantled.It was listed on the National Register of Historic Places in 1974, and was delisted in 2017

William Scott Farmstead, also known as the Roberts House and Ennis Pond House, is a historic home located near Windsor, Isle of Wight County, Virginia. The house was built about 1775, and is a two-story, five-bay, gable roofed brick dwelling. It has a rear frame addition dated to the mid- to late-19th century. The front facade features a pedimented one bay porch supported by Doric order columns. The interior retains much of its early Federal interior woodwork. Also on the property are the contributing servants' quarters, smokehouse, barn, and corn crib.It was listed on the National Register of Historic Places in 1991.

Windsor High School is a public high school located in Windsor, Virginia in Isle of Wight County.

Windsor is an incorporated town in Isle of Wight County in the Hampton Roads region of southeastern Virginia in the United States. It is located near the crossroads of U.S. Route 460 and U.S. Route 258. The population was 2,626 at the 2010 census, up from 916 at the 2000 census.

Smithfield Historic District is a national historic district located at Smithfield, Isle of Wight County, Virginia. It encompasses 289 contributing buildings and 2 contributing structures in the historic downtown and surrounding residential areas of Smithfield. There are 211 houses, 37 commercial buildings, 1 warehouse, 4 churches, 10 barns, 1 smokehouse, 23 garages, 1 farm office, 1 colonial kitchen, and 2 corncrib structures. Notable buildings include the original county clerk's office (1799), county jail, Wentworth-Barrett House (c. 1752), Wentworth–Grinnan House (c. 1780), King-Atkinson House (c. 1800), Smith-Morrison House (1770s), Hayden Hall (c. 1810, c. 1846), Boykin House (c. 1876), Goodrich House (1886), Thomas House (1889), Smithfield Academy (1827), Christ Episcopal Church (1832, 1892), and Hill Street Baptist Church (1923). Located in the district and separately listed are the Old Isle of Wight Courthouse, Smithfield Inn, Windsor Castle Farm, and P. D. Gwaltney Jr. House.It was listed on the National Register of Historic Places in 1973.

Henry Saunders House is a historic home located near Windsor, Isle of Wight County, Virginia, United States. The house was built about 1796, and is a 1+1⁄2-story, three bay Georgian style frame dwelling. It has a gable roof with dormers and a one-story side wing. Also on the property are four additional contributing buildings and one contributing structure.It was listed on the National Register of Historic Places in 1991.